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Copper-Catalyzed Double Friedel-Crafts Alkylation of Tetrahydroquinolines Under Aqueous Conditions: Efficient Synthesis of gem-Diarylacetic Esters

2020-01-13 08:41:19


Daggupati V. Ramana,[a] Karu Sudheer Kumar,[a,b] Ealeswarapu Srujana,[a] and Malapaka Chandrasekharam

 

 

Introduction
Ester, amide and amino groups are widely present in bioactive molecules and their incorporation into an organic molecule warrants multistep synthesis sequence. However, functionaliza- tion of inexpensive glycine ester or amide would be an effective strategy and represent important building blocks for drug de- velopment and natural product synthesis. Alkylation of arenes and heteroarenes is a challenging task in organic chemistry and Friedel-Crafts reaction is known to be the most suitable  choice.[1] Traditionally alkyl halides and alcohols have  been  used as alkylating agents and particularly benzyl halides, benzyl alcohols and styrenes are suitable electrophiles for the genera- tion of 1,1-diarylalkanes. New developments in the Friedel- Crafts alkylation and their efficacy in aqueous media have been recently reviewed.[2] Double Friedel-Crafts alkylation of indoles with non-symmetrical divinyl ketones was achieved for the syn- thesis of complex tricyclic indoles.[3] Though double Friedel- Crafts alkylation provides easy entry to gem-diaryl alkyl com- pounds,[4] reports on glycine esters as alkylating agents in Frie- del-Crafts reactions are not very common. Several reports ap- peared on the α-C-H functionalization of glycine esters/amides using various nucleophiles in presence of metal or metal-free catalysts in organic solvents.[5] Congde Huo reported copper- catalyzed oxidative arylation of glycine derivatives with indoles in THF/H2O.[6] The same group also reported a very interesting triarylaminium salt-promoted synthesis of bisindolyl acetic esters from glycine ester derivatives where the scope of the nucleophile is limited to indole and industrially unacceptable DCM solvent was used.[7]

 

We have previously demonstrated the copper-catalyzed α- arylation,[8] amidation/imidation[9] of N-arylglycine esters under mild conditions. Tetrahydroquinolines (THQs) belong to a class of heterocycles of high pharmacological value and in general organic reactions in water as solvent attracted tremendous in- terest over other organic solvents due to its green and environ- mentally benign nature.[10] Therefore an efficient method  for the synthesis of α-diaryl alkyl compounds from aryl/heteroaryl nucleophiles promoted by green solvents is highly warranted.   In continuation of our interest in C-H functionalizations involv- ing the most abundant, less expensive, non-toxic iron and cop- per catalysts and water-mediated reactions,[11] we herein report  a double Friedel-Crafts alkylation reaction of glycine ester on heteroaryl (tetrahydroquinolines, 2-meTHQ and indoles) and  aryl (N-methyl aniline) nucleophiles to generate gem-diaryl/het- eroarylacetic esters with less expensive, non-toxic copper cata- lyst and environmentally benign aqueous conditions.

 

Results and Discussion
Methyl 2-(p-tolylamino)acetate 1a and tetrahydroquinoline 2a were chosen as model substrates and the reaction was con- ducted in the presence of 10 mol-% CuCl in DCE solvent  at  room temperature for 24 h under open flask conditions, antici- pating the formation of tetrahydroquinolinyl glycine ester deriv- ative resulting from α-C-H functionalization. However the formation of methyl 2,2-bis(1,2,3,4-tetrahydroquinolin-6-yl)- acetate 3aa (10 %) was observed along with the expected prod- uct (R)-methyl 2-(1,2,3,4-tetrahydroquinolin-6-yl)-2-(p-tolyl- amino)acetate 3aa (25 %). This result instigated us to optimize the conditions for the unexpected double Friedel-Crafts alkyl- ation product 3aa (Table 1). Various solvents were  tested  for this reaction and water was found to be the most suitable sol- vent for the predominant formation of the double Friedel-Crafts alkylation product 3aa (entries 2–11, Table 1). The solvents DCE, ACN, DCM, THF and toluene at room temperature favored the formation of 3aa, whereas the reaction conducted at 100 °C in toluene solvent resulted in the exclusive  formation  of  3aa  in 23 %. While in MeOH, the selectivity and the overall yields were not encouraging, the reaction is not efficient in p-xylene solvent even at elevated (120° C) reaction temperature. The reaction is not successful with the solvents, DMF and DMSO, and the start- ing materials remained unreacted even at 120 °C. Among the catalysts CuI, CuII and FeCl3 employed for the reaction, CuI pro- duced an improved yield of 3aa (entries 12–17, Table 1). The conditions were then optimized for the reaction temperature, time and the catalyst loading under water solvent and CuI cata- lyst conditions (entries 18–23, Table 1). In the absence of a cata- lyst, the reaction does not proceed  (entry 24, Table  1). Under  the optimized reaction conditions, stirring the reaction mixture with 10 mol-% of CuI  catalyst  in  water  solvent  at  100  °C  for 24 h, the desired product 3aa was obtained in 85 % yield.

 

With the optimised conditions in hand, we examined the substrate scope for the double Friedel-Crafts alkylation reaction of glycine esters/amide with different nucleophiles i.e., 2- meTHQ, substituted indoles and N-methyl aniline to generate diverse gem-di-aryl/-heteroarylacetic esters/amide. Different N- arylglycine ester derivatives (R = Me, Et, nBu, iPr, tBu and Bn) were treated with THQ under the optimised reaction conditions to produce the corresponding desired products in excellent yields (3aa–3fa, Table 2). The scope of the nucleophile was suc- cessfully extended to 2-meTHQ, N-methyl aniline and 1-, 5- and 6,7-disubstituted indole derivatives. The copper-catalyzed reac- tion proceeds smoothly with 2-meTHQ and N-arylglycine ester 1a resulting in  the  formation  of  the  desired  product  3ab  in 65 % yield (Table 2). N-methyl aniline was treated with different N-arylglycine esters (R = Me, Bn) and the reactions proceeded well to afford the corresponding desired products in  good  yields (3ac, 3fc, Table 2). Various substituted indoles employed as nucleophiles, for the double Friedel-Crafts alkylation reaction protocol with N-arylglycine ester 1a, delivered the correspond- ing products in good to excellent yields (3ad–3ag, Table 2). Under the optimized reaction conditions, we also observed the formation of α-C-H functionalization products in some of the cases, in very low yields.

 

The double Friedel-Crafts alkylation reaction protocol also works for the glycine amide derivative, 1-(pyrrolidin-1-yl)-2-(p- tolylamino) ethanone using 2-meTHQ or indole as nucleophiles, and delivered the corresponding alkylated products in very  good yields (Scheme 1).
To understand the mechanism for the double Friedel-Crafts alkylation reaction, we carried out the following experiments as depicted in the Scheme 2. When the reaction was carried out in the presence of radical scavenger BHT (20 mol-%) under the standard conditions, the absence of the formation of the dou- ble Friedel-Crafts product and α-C-H functionalization product indicates that the reaction follows a radical-mediated path. The reaction did not proceed in the absence of  oxygen  implying that molecular oxygen is essential for the reaction to proceed. The intermediacy of the α-C-H functionalization  is  confirmed  by the formation of the double Friedel-Crafts alkylated product in 58 % yield from the reaction of 3aa  (0.5  mmol)  with  THQ (1.0 mmol).

 

Based on previous literature reports and our recent investiga- tions on CuI-catalyzed α-C-H functionalizations adjacent to the nitrogen atom, we proposed a plausible mechanism for this double Friedel-Crafts alkylation reaction as shown in the  Scheme 3. Initially, CuI in presence of atmospheric oxygen gen- erates CuIIOO radical, which might abstract hydrogen radical from glycine derivative 1 delivering radical intermediate A, fur- ther interconverts to the iminium intermediate B. Nucleophile attack on intermediate B resulted in the α-C-H functionalization product 3. Then a second oxidation occurred on 3 compound to form another iminium intermediate C, followed by nucleo- phile addition resulted in the intermediate D. Finally, the double Friedel-Crafts alkylated product produced from the intermedi- ate D, by the loss of aniline.

 

Conclusions
In conclusion, we have successfully demonstrated a double Frie- del-Crafts reaction protocol of N-arylglycine esters/amide with heteroaryl (tetrahydroquinolines, 2-meTHQ and indoles) and  aryl (N-methyl aniline) nucleophiles. Under the reaction condi- tions both the α-C-H functionalization and gem-diaryl/hetero- arylacetic esters/amide could be generated, however in the present investigation, the reaction conditions are optimized for double Friedel-Crafts products in excellent yields. The reaction   is carried out with a less  expensive,  non-toxic copper  catalyst  in aqueous and open flask conditions. A single electron transfer (SET) mechanism was proposed for the reaction.

 

Experimental Section
General Procedure for the Preparation of Compound 3: A mix- ture of N-arylglycine esters 1  (1 mmol), tetrahydroquinoline/2- meTHQ/N-methylaniline/indole 2  (2  mmol)  and  CuI  (0.1  mmol,  10 mol-%) in water (2 mL) solvent was stirred at 100 °C under open air (TLC) Subsequently, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The organic layer was dried with anhydrous Na2SO4 and then the solvent was removed under reduced pressure. The resulting mixture was concentrated under vacuum and the residue was purified by column chromatog- raphy (silica gel, petroleum ether/ethyl acetate as an eluent) to af- ford the desired coupling products 3.

 

Acknowledgments
DVR grateful to the University Grant Commission (UGC), New Delhi, India for the award of Senior Research Fellowship (SRF).

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2-Methyl-3-nitrophenylboronic acid

Catalog No.:AA00HAW2

CAS No.:1072945-60-8 MDL No.:MFCD06201025

MF:C7H8BNO4 MW:180.9537

89-55-4

7-Fluoro-2-methylquinoline-8-boronic acid

Catalog No.:AA003BW8

CAS No.:1072945-61-9 MDL No.:MFCD11504838

MF:C10H9BFNO2 MW:204.9934

89-55-4

4-(Ethylsulfonamido)phenylboronic acid

Catalog No.:AA007WM0

CAS No.:1072945-62-0 MDL No.:MFCD10699608

MF:C8H12BNO4S MW:229.0612

89-55-4

3-(Propylsulfonamido)phenylboronic acid

Catalog No.:AA0084ZE

CAS No.:1072945-64-2 MDL No.:MFCD10699610

MF:C9H14BNO4S MW:243.0878

89-55-4

3-(Butylsulfonamido)phenylboronic acid

Catalog No.:AA007WLZ

CAS No.:1072945-65-3 MDL No.:MFCD10699611

MF:C10H16BNO4S MW:257.1143

89-55-4

4-(Butylsulfonamido)phenylboronic acid

Catalog No.:AA003K3Y

CAS No.:1072945-66-4 MDL No.:MFCD10699612

MF:C10H16BNO4S MW:257.1143

89-55-4

3-(Cyclopropanesulfonamido)phenylboronic acid

Catalog No.:AA007EPO

CAS No.:1072945-67-5 MDL No.:MFCD10699613

MF:C9H12BNO4S MW:241.0719

89-55-4

4-(Cyclopropanesulfonamido)phenylboronic acid

Catalog No.:AA0090C6

CAS No.:1072945-68-6 MDL No.:MFCD10699614

MF:C9H12BNO4S MW:241.0719

89-55-4

4-Chloropyridine-3-boronic acid , HCl

Catalog No.:AA007EPN

CAS No.:1072945-69-7 MDL No.:MFCD09972093

MF:C5H6BCl2NO2 MW:193.8236

89-55-4

3-Fluoro-4-(5-methyl-1,3,4-oxadiazol-2-yl)phenylboronic acid

Catalog No.:AA007WLY

CAS No.:1072945-71-1 MDL No.:MFCD09972094

MF:C9H8BFN2O3 MW:221.9808

89-55-4

3-(2-(Piperidin-1-yl)ethylcarbamoyl)phenylboronic acid, HCl

Catalog No.:AA008SR9

CAS No.:1072945-72-2 MDL No.:MFCD11053816

MF:C14H22BClN2O3 MW:312.6001

89-55-4

3-(Cyclohexyl(methyl)carbamoyl)phenylboronic acid

Catalog No.:AA007EPM

CAS No.:1072945-73-3 MDL No.:MFCD09972095

MF:C14H20BNO3 MW:261.1245

89-55-4

4-(2-Morpholinoethoxy)phenylboronic acid, HCl

Catalog No.:AA003JXH

CAS No.:1072945-74-4 MDL No.:MFCD10699615

MF:C12H19BClNO4 MW:287.5476

89-55-4

6-Bromo-4-methylpyridine-3-boronic acid

Catalog No.:AA003N1O

CAS No.:1072945-75-5 MDL No.:MFCD09037489

MF:C6H7BBrNO2 MW:215.8403

89-55-4

2-Chloro-6-fluoro-3-methoxyphenylboronic acid

Catalog No.:AA0090CD

CAS No.:1072945-77-7 MDL No.:MFCD09972096

MF:C7H7BClFO3 MW:204.3911

89-55-4

1-(6-Chloropyrimidin-4-yl)pyrazole-4-boronic acid

Catalog No.:AA003CZ2

CAS No.:1072945-81-3 MDL No.:MFCD09972097

MF:C7H6BClN4O2 MW:224.4121

89-55-4

4-(4-Nitrophenoxy)phenylboronic acid

Catalog No.:AA0090C5

CAS No.:1072945-82-4 MDL No.:MFCD10699618

MF:C12H10BNO5 MW:259.0225

89-55-4

4-(Carboxymethoxy)phenylboronic acid

Catalog No.:AA007WLX

CAS No.:1072945-84-6 MDL No.:MFCD03425920

MF:C8H9BO5 MW:195.9651

89-55-4

2-Acetamido-5-chlorophenylboronic acid

Catalog No.:AA003BIM

CAS No.:1072945-85-7 MDL No.:MFCD11504839

MF:C8H9BClNO3 MW:213.4260

89-55-4

6-(Methoxycarbonyl)pyridine-3-boronic acid

Catalog No.:AA007EPL

CAS No.:1072945-86-8 MDL No.:MFCD09800559

MF:C7H8BNO4 MW:180.9537

89-55-4

1-Methyl-1H-benzoimidazole-6-boronic acid

Catalog No.:AA007WLW

CAS No.:1072945-87-9 MDL No.:MFCD09972099

MF:C8H9BN2O2 MW:175.9803

89-55-4

1-(3-Chlorophenyl)pyrazole-4-boronic acid

Catalog No.:AA008SSG

CAS No.:1072945-88-0 MDL No.:MFCD09878353

MF:C9H8BClN2O2 MW:222.4360

89-55-4

1-(2-Chlorophenyl)pyrazole-4-boronic acid

Catalog No.:AA003CRB

CAS No.:1072945-91-5 MDL No.:MFCD09972101

MF:C9H8BClN2O2 MW:222.4360

89-55-4

1-p-Tolylpyrazole-4-boronic acid

Catalog No.:AA00386F

CAS No.:1072945-92-6 MDL No.:MFCD09972102

MF:C10H11BN2O2 MW:202.0175

89-55-4

3-(4-Nitrophenoxy)phenylboronic acid

Catalog No.:AA007EPK

CAS No.:1072945-93-7 MDL No.:MFCD09972103

MF:C12H10BNO5 MW:259.0225

89-55-4

3-(2-Nitro-4-trifluoromethylphenoxy)phenylboronic acid

Catalog No.:AA007WLV

CAS No.:1072945-94-8 MDL No.:MFCD09972104

MF:C13H9BF3NO5 MW:327.0205

89-55-4

3-(2-Nitrophenoxy)phenylboronic acid

Catalog No.:AA007EPJ

CAS No.:1072945-95-9 MDL No.:MFCD09972105

MF:C12H10BNO5 MW:259.0225

89-55-4

Ethyl (3-boronobenzoylamino)acetate

Catalog No.:AA007EPI

CAS No.:1072945-97-1 MDL No.:MFCD09878356

MF:C11H14BNO5 MW:251.0436

89-55-4

2-Chloro-5-methoxypyridine-4-boronic acid

Catalog No.:AA003BK0

CAS No.:1072945-98-2 MDL No.:MFCD09972106

MF:C6H7BClNO3 MW:187.3887

89-55-4

4-Cyanopyridine-2-boronic acid

Catalog No.:AA003L6T

CAS No.:1072946-01-0 MDL No.:MFCD08703250

MF:C6H5BN2O2 MW:147.9271

89-55-4

3-(p-Tolylcarbamoyl)phenylboronic acid

Catalog No.:AA003I78

CAS No.:1072946-03-2 MDL No.:MFCD10699620

MF:C14H14BNO3 MW:255.0769

89-55-4

N-(3-Chloro-4-fluorophenyl) 3-boronobenzamide

Catalog No.:AA003BN6

CAS No.:1072946-04-3 MDL No.:MFCD09972110

MF:C13H10BClFNO3 MW:293.4858

89-55-4

3-Boronoisonicotinic acid

Catalog No.:AA003IWD

CAS No.:1072946-05-4 MDL No.:MFCD10696649

MF:C6H6BNO4 MW:166.9271

89-55-4

3-(3-Isopropylthioureido)phenylboronic acid

Catalog No.:AA0090CS

CAS No.:1072946-07-6 MDL No.:MFCD09972112

MF:C10H15BN2O2S MW:238.1143

89-55-4

Ethyl (4-boronobenzoylamino)acetate

Catalog No.:AA003BR1

CAS No.:1072946-08-7 MDL No.:MFCD09972113

MF:C11H14BNO5 MW:251.0436

89-55-4

4-Fluoro-2,5-dimethylphenylboronic acid

Catalog No.:AA007WLG

CAS No.:1072946-10-1 MDL No.:MFCD10699621

MF:C8H10BFO2 MW:167.9732

89-55-4

3-Fluoro-4-(4-methoxybenzylthio)phenylboronic acid

Catalog No.:AA007WLF

CAS No.:1072946-13-4 MDL No.:MFCD10699622

MF:C14H14BFO3S MW:292.1336

89-55-4

4-(2-Cyanovinyl)phenylboronic acid

Catalog No.:AA0084ZC

CAS No.:1072946-14-5 MDL No.:MFCD09972115

MF:C9H8BNO2 MW:172.9763

89-55-4

N-(3,4-Difluorophenyl) 3-boronobenzamide

Catalog No.:AA0090CA

CAS No.:1072946-15-6 MDL No.:MFCD09972116

MF:C13H10BF2NO3 MW:277.0312

89-55-4

4-(Methylsulfonyl)-2-(trifluoromethyl)phenylboronic acid

Catalog No.:AA0037XX

CAS No.:1072946-16-7 MDL No.:MFCD10699623

MF:C8H8BF3O4S MW:268.0179

89-55-4

3-(3-Methylthioureido)phenylboronic acid

Catalog No.:AA0090BX

CAS No.:1072946-17-8 MDL No.:MFCD09972118

MF:C8H11BN2O2S MW:210.0611

89-55-4

4-(3-Methylthioureido)phenylboronic acid

Catalog No.:AA007WLE

CAS No.:1072946-18-9 MDL No.:MFCD10699624

MF:C8H11BN2O2S MW:210.0611

89-55-4

2-Chloro-4-methoxypyridine-3-boronic acid

Catalog No.:AA003BJY

CAS No.:1072946-19-0 MDL No.:MFCD09972119

MF:C6H7BClNO3 MW:187.3887

89-55-4

6-(4-Methoxybenzylcarbamoyl)pyridine-3-boronic acid

Catalog No.:AA0084ZB

CAS No.:1072946-22-5 MDL No.:MFCD10699628

MF:C14H15BN2O4 MW:286.0909

89-55-4

Monolithium 4-methoxypyridine-3-boronate

Catalog No.:AA003S2V

CAS No.:1072946-24-7 MDL No.:MFCD10699631

MF:C6H7BLiNO3 MW:158.8767

89-55-4

2-Chloro-6-methoxypyridine-3-boronic acid

Catalog No.:AA008SRM

CAS No.:1072946-25-8 MDL No.:MFCD11053826

MF:C6H7BClNO3 MW:187.3887

89-55-4

2-Chloro-5-methoxypyridine-3-boronic acid

Catalog No.:AA007WLD

CAS No.:1072946-26-9 MDL No.:MFCD10699632

MF:C6H7BClNO3 MW:187.3887

89-55-4

3-(Diethylcarbamoyl)-2-fluorophenylboronic acid

Catalog No.:AA007WLC

CAS No.:1072946-28-1 MDL No.:MFCD10699633

MF:C11H15BFNO3 MW:239.0511

89-55-4

4-(1-BOC-piperidin-4-yloxy)-2-methoxyphenylboronic acid

Catalog No.:AA003JV5

CAS No.:1072946-29-2 MDL No.:MFCD10699635

MF:C17H26BNO6 MW:351.2024

89-55-4

4-(1-BOC-piperidin-4-yloxy)-3-methoxyphenylboronic acid

Catalog No.:AA003JV6

CAS No.:1072946-30-5 MDL No.:MFCD10699636

MF:C17H26BNO6 MW:351.2024

89-55-4

4-Pentylcyclohex-1-enylboronic acid

Catalog No.:AA003BTU

CAS No.:1072946-31-6 MDL No.:MFCD10699637

MF:C11H21BO2 MW:196.0942

89-55-4

5-Chloro-2-methyl-4-(trifluoromethyl)phenylboronic acid

Catalog No.:AA003MKK

CAS No.:1072946-33-8 MDL No.:MFCD11053801

MF:C8H7BClF3O2 MW:238.3992

89-55-4

3,4,5-Trichloro-2-methylphenylboronic acid

Catalog No.:AA003IBK

CAS No.:1072946-34-9 MDL No.:MFCD11053802

MF:C7H6BCl3O2 MW:239.2913

89-55-4

4-Boronophthalic acid

Catalog No.:AA00386E

CAS No.:1072946-35-0 MDL No.:MFCD11053803

MF:C8H7BO6 MW:209.9486

89-55-4

2,6-Dichloro-3-nitrophenylboronic acid

Catalog No.:AA007EPD

CAS No.:1072946-37-2 MDL No.:MFCD10699640

MF:C6H4BCl2NO4 MW:235.8173

89-55-4

2,3,4-Trichloro-5-nitrophenylboronic acid

Catalog No.:AA003FB9

CAS No.:1072946-38-3 MDL No.:MFCD11053804

MF:C6H3BCl3NO4 MW:270.2623

89-55-4

2,6-Dichlorobenzylboronic acid

Catalog No.:AA003BIC

CAS No.:1072946-39-4 MDL No.:MFCD11053805

MF:C7H7BCl2O2 MW:204.8463

89-55-4

4-(1,3-Dioxolan-2-yl)-2,6-difluorophenylboronic acid

Catalog No.:AA00386D

CAS No.:1072946-41-8 MDL No.:MFCD11053806

MF:C9H9BF2O4 MW:229.9732

89-55-4

4-(Aminomethyl)-3-fluorophenylboronic acid, HCl

Catalog No.:AA008SR6

CAS No.:1072946-45-2 MDL No.:MFCD11053810

MF:C7H10BClFNO2 MW:205.4222

89-55-4

5-(Aminomethyl)-2-fluorophenylboronic acid, HCl

Catalog No.:AA007EPC

CAS No.:1072946-46-3 MDL No.:MFCD11053811

MF:C7H10BClFNO2 MW:205.4222

89-55-4

5-((Boc-Amino)methyl)furan-2-boronic acid

Catalog No.:AA003BUP

CAS No.:1072946-49-6 MDL No.:MFCD11053783

MF:C10H16BNO5 MW:241.0487

89-55-4

6-Chloro-2-methoxypyridine-3-boronic acid

Catalog No.:AA0084ZA

CAS No.:1072946-50-9 MDL No.:MFCD11053817

MF:C6H7BClNO3 MW:187.3887

89-55-4

3-(1,3-Dioxolan-2-yl)-5-(trifluoromethyl)phenylboronic acid

Catalog No.:AA003BNA

CAS No.:1072946-51-0 MDL No.:MFCD00008782

MF:C10H10BF3O4 MW:261.9902

89-55-4

2-(Bromomethyl)-3,4,5-trichlorophenylboronic acid

Catalog No.:AA003BHA

CAS No.:1072946-53-2 MDL No.:MFCD11053838

MF:C7H5BBrCl3O2 MW:318.1874

89-55-4

3-(2-(Piperidin-1-yl)ethylcarbamoyl)phenylboronic acid

Catalog No.:AA007WLA

CAS No.:1072946-54-3 MDL No.:MFCD11053842

MF:C14H21BN2O3 MW:276.1391

89-55-4

5-(3-Boronophenyl)pentanoic acid

Catalog No.:AA003M1N

CAS No.:1072946-56-5 MDL No.:MFCD11053844

MF:C11H15BO4 MW:222.0454

89-55-4

3-(4-Carboethoxybutyl)phenylboronic acid

Catalog No.:AA003BNB

CAS No.:1072946-57-6 MDL No.:MFCD11053845

MF:C13H19BO4 MW:250.0986

89-55-4

2-Ethoxypyridine-4-boronic acid

Catalog No.:AA003H3V

CAS No.:1072946-58-7 MDL No.:MFCD07374989

MF:C7H10BNO3 MW:166.9702

89-55-4

2-Carboxypyridine-4-boronic acid

Catalog No.:AA003KRM

CAS No.:1072946-59-8 MDL No.:MFCD11504842

MF:C6H6BNO4 MW:166.9271

89-55-4

1-(4-Carboxybutyl)indole-5-boronic acid

Catalog No.:AA003M3N

CAS No.:1072946-60-1 MDL No.:MFCD11053846

MF:C13H16BNO4 MW:261.0814

89-55-4

3-(4-Carboxybutoxy)-2,4,6-trifluorophenylboronic acid

Catalog No.:AA003I10

CAS No.:1072946-61-2 MDL No.:MFCD11504843

MF:C11H12BF3O5 MW:292.0162

89-55-4

2-Chloro-3-fluoropyridine-5-boronic acid

Catalog No.:AA003BW3

CAS No.:1072946-66-7 MDL No.:MFCD04112500

MF:C5H4BClFNO2 MW:175.3532

89-55-4

2,4,6-Trifluoro-3-hydroxyphenylboronic acid

Catalog No.:AA003BHY

CAS No.:1072951-37-1 MDL No.:MFCD11053885

MF:C6H4BF3O3 MW:191.9004

89-55-4

5-(BOC-Aminomethyl)thiophene-2-boronic acid

Catalog No.:AA00389P

CAS No.:1072951-39-3 MDL No.:MFCD11504845

MF:C10H16BNO4S MW:257.1143

89-55-4

2-Fluoro-5-(morpholine-4-carbonyl)phenylboronic acid

Catalog No.:AA003BKC

CAS No.:1072951-41-7 MDL No.:MFCD11504847

MF:C11H13BFNO4 MW:253.0346

89-55-4

2-(Methoxycarbonyl)-4-(trifluoromethyl)phenylboronic acid

Catalog No.:AA003BHE

CAS No.:1072951-42-8 MDL No.:MFCD11504848

MF:C9H8BF3O4 MW:247.9636

89-55-4

2-Bromo-5-fluoropyridine-4-boronic acid

Catalog No.:AA007EPA

CAS No.:1072951-43-9 MDL No.:MFCD04973353

MF:C5H4BBrFNO2 MW:219.8042

89-55-4

6-Fluoroquinoline-8-boronic acid

Catalog No.:AA003BW6

CAS No.:1072951-44-0 MDL No.:MFCD11504849

MF:C9H7BFNO2 MW:190.9668

89-55-4

5-Fluoroquinoline-8-boronic acid

Catalog No.:AA003BVA

CAS No.:1072951-45-1 MDL No.:MFCD11504850

MF:C9H7BFNO2 MW:190.9668

89-55-4

8-Trifluoromethoxyquinoline-5-boronic acid

Catalog No.:AA007EP9

CAS No.:1072951-46-2 MDL No.:MFCD11504851

MF:C10H7BF3NO3 MW:256.9737

89-55-4

8-Trifluoromethylquinoline-6-boronic acid

Catalog No.:AA007WL9

CAS No.:1072951-47-3 MDL No.:MFCD11504852

MF:C10H7BF3NO2 MW:240.9743

89-55-4

3-Bromo-5-(trifluoromethoxy)phenylboronic acid

Catalog No.:AA007EP8

CAS No.:1072951-48-4 MDL No.:MFCD11504853

MF:C7H5BBrF3O3 MW:284.8230

89-55-4

2-Hydroxy-4-trifluoromethylphenylboronic acid

Catalog No.:AA0084Z9

CAS No.:1072951-50-8 MDL No.:MFCD03094996

MF:C7H6BF3O3 MW:205.9269

89-55-4

3,4-Bis(methoxycarbonyl)phenylboronic acid

Catalog No.:AA0084Z8

CAS No.:1072951-51-9 MDL No.:MFCD11504854

MF:C10H11BO6 MW:238.0017

89-55-4

2-Fluoro-5-pentanoylphenylboronic acid

Catalog No.:AA003BKF

CAS No.:1072951-52-0 MDL No.:MFCD11504855

MF:C11H14BFO3 MW:224.0365

89-55-4

2,6-Dichloropyridine-4-boronic acid

Catalog No.:AA008XCV

CAS No.:1072951-54-2 MDL No.:MFCD09751352

MF:C5H4BCl2NO2 MW:191.8078

89-55-4

5-Trifluoromethylquinoline-8-boronic acid

Catalog No.:AA003BUR

CAS No.:1072951-55-3 MDL No.:MFCD11504856

MF:C10H7BF3NO2 MW:240.9743

89-55-4

5-Bromo-2-trifluoromethoxyphenylboronic acid

Catalog No.:AA0090CK

CAS No.:1072951-56-4 MDL No.:MFCD11504857

MF:C7H5BBrF3O3 MW:284.8230

89-55-4

4-[(2-Isopropyl-5-methylphenoxy)methyl]phenylboronic acid

Catalog No.:AA007WFI

CAS No.:1072951-58-6 MDL No.:MFCD08276834

MF:C17H21BO3 MW:284.1578

89-55-4

3,5-Diiodo-2-methoxyphenylboronic acid

Catalog No.:AA003IKQ

CAS No.:1072951-59-7 MDL No.:MFCD08457647

MF:C7H7BI2O3 MW:403.7486

89-55-4

2-((3-(Trifluoromethyl)phenoxy)methyl)phenylboronic acid

Catalog No.:AA0084Z7

CAS No.:1072951-60-0 MDL No.:MFCD09038421

MF:C14H12BF3O3 MW:296.0495

89-55-4

3-(3'-Fluorobenzyloxy)phenylboronic acid

Catalog No.:AA003BN7

CAS No.:1072951-62-2 MDL No.:MFCD08276822

MF:C13H12BFO3 MW:246.0420

89-55-4

2-[(2',6'-Diisopropylphenoxy)methyl]phenylboronic acid

Catalog No.:AA003G4V

CAS No.:1072951-64-4 MDL No.:MFCD08705265

MF:C19H25BO3 MW:312.2110

89-55-4

2-[(4'-Chloro-1-naphthyloxy)methyl]phenylboronic acid

Catalog No.:AA003G55

CAS No.:1072951-65-5 MDL No.:MFCD08705266

MF:C17H14BClO3 MW:312.5553

89-55-4

4-[(4-tert-Butyl-2-methylphenoxy)methyl]phenylboronic acid

Catalog No.:AA007EP7

CAS No.:1072951-67-7 MDL No.:MFCD09265139

MF:C18H23BO3 MW:298.1844

89-55-4

3-[(2'-Isopropyl-5'-methylphenoxy)methyl]phenylboronic acid

Catalog No.:AA003IOK

CAS No.:1072951-74-6 MDL No.:MFCD22200781

MF:C17H21BO3 MW:284.1578

89-55-4

2-[(4'-tert-Butyl-2'-methylphenoxy)methyl]phenylboronic acid

Catalog No.:AA003G5A

CAS No.:1072951-76-8 MDL No.:MFCD08276830

MF:C18H23BO3 MW:298.1844

89-55-4

4-(2'-Fluorobenzyloxy)phenylboronic acid

Catalog No.:AA003BR2

CAS No.:1072951-78-0 MDL No.:MFCD08705274

MF:C13H12BFO3 MW:246.0420

89-55-4

4-(4'-Isopentyloxyphenyl)phenylboronic acid

Catalog No.:AA003BRA

CAS No.:1072951-81-5 MDL No.:MFCD08276971

MF:C17H21BO3 MW:284.1578

89-55-4

3,5-Dibromo-2-fluorophenylboronic acid

Catalog No.:AA003BNQ

CAS No.:1072951-82-6 MDL No.:MFCD08276977

MF:C6H4BBr2FO2 MW:297.7122

89-55-4

3-Bromo-5-butoxyphenylboronic acid

Catalog No.:AA003BOJ

CAS No.:1072951-84-8 MDL No.:MFCD08457637

MF:C10H14BBrO3 MW:272.9314

89-55-4

6-Bromo-2-fluoro-3-propoxyphenylboronic acid

Catalog No.:AA003N14

CAS No.:1072951-85-9 MDL No.:MFCD09038422

MF:C9H11BBrFO3 MW:276.8952

89-55-4

3-Bromo-2-isopropoxy-5-formylphenylboronic acid

Catalog No.:AA003IXT

CAS No.:1072951-86-0 MDL No.:MFCD09750471

MF:C10H12BBrO4 MW:286.9149

89-55-4

2-[(2-Isopropyl-5-methylphenoxy)methyl]phenylboronic acid

Catalog No.:AA003G4X

CAS No.:1072951-87-1 MDL No.:MFCD08276821

MF:C17H21BO3 MW:284.1578

89-55-4

6-Bromo-3-butoxy-2-fluorophenylboronic acid

Catalog No.:AA003N1B

CAS No.:1072951-88-2 MDL No.:MFCD08276825

MF:C10H13BBrFO3 MW:290.9218

89-55-4

3-(4-Methoxybenzyloxy)phenylboronic acid

Catalog No.:AA0084TO

CAS No.:1072951-89-3 MDL No.:MFCD09038416

MF:C14H15BO4 MW:258.0775

89-55-4

3-[(4-Chloro-3-methylphenoxy)methyl]phenylboronic acid

Catalog No.:AA003ION

CAS No.:1072951-91-7 MDL No.:MFCD09265140

MF:C14H14BClO3 MW:276.5232

89-55-4

3,5-Dimethyl-4-(3',5'-dimethoxybenzyloxy)phenylboronic acid

Catalog No.:AA007EP6

CAS No.:1072951-94-0 MDL No.:MFCD22421632

MF:C17H21BO5 MW:316.1566

89-55-4

2-Bromo-3-butoxy-6-fluorophenylboronic acid

Catalog No.:AA003GJT

CAS No.:1072951-95-1 MDL No.:MFCD08276824

MF:C10H13BBrFO3 MW:290.9218

89-55-4

4-(3'-Fluorobenzyloxy)phenylboronic acid

Catalog No.:AA003JYC

CAS No.:1072951-98-4 MDL No.:MFCD00010512

MF:C13H12BFO3 MW:246.0420

89-55-4

3-Formyl-4-isopropoxyphenylboronic acid

Catalog No.:AA003BPN

CAS No.:1072952-00-1 MDL No.:MFCD08705272

MF:C10H13BO4 MW:208.0188

89-55-4

3-(2'-Methoxybenzyloxy)phenylboronic acid

Catalog No.:AA0084TN

CAS No.:1072952-02-3 MDL No.:MFCD08276833

MF:C14H15BO4 MW:258.0775

89-55-4

3-(4'-Fluorobenzyloxy)phenylboronic acid

Catalog No.:AA003I06

CAS No.:1072952-03-4 MDL No.:MFCD08705238

MF:C13H12BFO3 MW:246.0420

89-55-4

3-Ethylsulfinylphenylboronic acid

Catalog No.:AA003BND

CAS No.:1072952-07-8 MDL No.:MFCD03092933

MF:C8H11BO3S MW:198.0471

89-55-4

3-Carboxy-2-fluorophenylboronic acid

Catalog No.:AA007EP5

CAS No.:1072952-09-0 MDL No.:MFCD03095128

MF:C7H6BFO4 MW:183.9295

89-55-4

2-Ethylsulfinylphenylboronic acid

Catalog No.:AA0084TM

CAS No.:1072952-11-4 MDL No.:MFCD03095262

MF:C8H11BO3S MW:198.0471

89-55-4

2-Amino-4,5-difluorophenylboronic acid

Catalog No.:AA003BIP

CAS No.:1072952-14-7 MDL No.:MFCD03095340

MF:C6H6BF2NO2 MW:172.9251

89-55-4

5-Hexenylboronic acid

Catalog No.:AA003QSK

CAS No.:1072952-16-9 MDL No.:MFCD10567048

MF:C6H13BO2 MW:127.9772

89-55-4

5-Chloro-2-fluoro-4-methoxyphenylboronic acid

Catalog No.:AA007EP3

CAS No.:1072952-18-1 MDL No.:MFCD04112552

MF:C7H7BClFO3 MW:204.3911

89-55-4

2-Isopropoxy-4-trifluoromethylphenylboronic acid

Catalog No.:AA007WFG

CAS No.:1072952-21-6 MDL No.:MFCD04972374

MF:C10H12BF3O3 MW:248.0067

89-55-4

2-Boronofuran-3-carboxylic acid

Catalog No.:AA0084TK

CAS No.:1072952-23-8 MDL No.:MFCD06203510

MF:C5H5BO5 MW:155.9012

89-55-4

2-Fluoro-5-hydroxymethylphenylboronic acid

Catalog No.:AA007WFF

CAS No.:1072952-25-0 MDL No.:MFCD06656276

MF:C7H8BFO3 MW:169.9460

89-55-4

2,6-Difluoropyridine-3-boronic acid hydrate

Catalog No.:AA003BIF

CAS No.:1072952-27-2 MDL No.:MFCD06657881

MF:C5H6BF2NO3 MW:176.9138

89-55-4

5-Formyl-3-methylthiophene-2-boronic acid

Catalog No.:AA003BVB

CAS No.:1072952-28-3 MDL No.:MFCD06657888

MF:C6H7BO3S MW:169.9940

89-55-4

2-Picoline-5-boronic acid hydrate

Catalog No.:AA008SSJ

CAS No.:1072952-30-7 MDL No.:MFCD06657901

MF:C6H10BNO3 MW:154.9595

89-55-4

2-Picoline-3-boronic acid HCl

Catalog No.:AA0033CQ

CAS No.:1072952-34-1 MDL No.:MFCD06659489

MF:C6H9BClNO2 MW:173.4052

89-55-4

3-Picoline-4-boronic acid HCl

Catalog No.:AA003BQ3

CAS No.:1072952-40-9 MDL No.:MFCD06659519

MF:C6H9BClNO2 MW:173.4052

89-55-4

5-Chloro-2-fluoro-4-methylphenylboronic acid

Catalog No.:AA0084TJ

CAS No.:1072952-42-1 MDL No.:MFCD07368241

MF:C7H7BClFO2 MW:188.3917

89-55-4

5-Hydroxy-2-methoxyphenylboronic acid

Catalog No.:AA003NVO

CAS No.:1072952-43-2 MDL No.:MFCD07368831

MF:C7H9BO4 MW:167.9550

89-55-4

3-Fluoro-5-methylpyridine-4-boronic acid

Catalog No.:AA003BPJ

CAS No.:1072952-44-3 MDL No.:MFCD07368843

MF:C6H7BFNO2 MW:154.9347

89-55-4

2-Fluoro-5-methylpyridine-3-boronic acid

Catalog No.:AA003BKD

CAS No.:1072952-45-4 MDL No.:MFCD07368857

MF:C6H7BFNO2 MW:154.9347

89-55-4

2-Bromo-5-methoxypyridine-4-boronic acid

Catalog No.:AA003BJ3

CAS No.:1072952-48-7 MDL No.:MFCD07781222

MF:C6H7BBrNO3 MW:231.8397

89-55-4

(4,5-Dimethoxy-2-(methoxycarbonyl)phenyl)boronic acid

Catalog No.:AA007WFD

CAS No.:1072952-49-8 MDL No.:MFCD07781232

MF:C10H13BO6 MW:240.0176

89-55-4

2-Fluoro-3-(ethoxycarbonyl)phenylboronic acid

Catalog No.:AA0084TH

CAS No.:1072952-52-3 MDL No.:MFCD08064050

MF:C9H10BFO4 MW:211.9827

89-55-4

3-Chloro-4-formylphenylboronic acid

Catalog No.:AA007EP1

CAS No.:1072952-53-4 MDL No.:MFCD08274473

MF:C7H6BClO3 MW:184.3847

89-55-4

Benzovindiflupyr

Catalog No.:AA01DZFR

CAS No.:1072957-71-1 MDL No.:MFCD30725523

MF:C18H15Cl2F2N3O MW:398.2340

89-55-4

Sr-3677

Catalog No.:AA008RLJ

CAS No.:1072959-67-1 MDL No.:MFCD16619390

MF:C22H24N4O4 MW:408.4504

89-55-4

1-Ethyl-1h-pyrazol-5-ol

Catalog No.:AA007EOZ

CAS No.:107296-34-4 MDL No.:MFCD13151912

MF:C5H8N2O MW:112.1298

89-55-4

4-(6-Methyl-4,8-dioxo-1,3,6,2-dioxazaborocan-2-yl)benzaldehyde

Catalog No.:AA01FGJ9

CAS No.:1072960-66-7 MDL No.:MFCD11215233

MF:C12H12BNO5 MW:261.0384

89-55-4

2-(4-Hydroxymethylphenyl)-2,3-dihydro-1h-naphtho[1,8-de][1,3,2]diazaborinine

Catalog No.:AA00HAW4

CAS No.:1072960-84-9 MDL No.:MFCD20527131

MF:C17H15BN2O MW:274.1248

89-55-4

Cyclopropaneaceticacid, 2-methylene-

Catalog No.:AA0084TG

CAS No.:1073-00-3 MDL No.:MFCD11558999

MF:C6H8O2 MW:112.1265

89-55-4

1,3,2-dioxathiane-2,2-dione

Catalog No.:AA00HAW5

CAS No.:1073-05-8 MDL No.:MFCD00801144

MF:C3H6O4S MW:138.1423

89-55-4

1-Bromo-3-fluorobenzene

Catalog No.:AA0032MW

CAS No.:1073-06-9 MDL No.:MFCD00000326

MF:C6H4BrF MW:174.9984

89-55-4

4,4-Dimethylcyclohex-2-enone

Catalog No.:AA008RLW

CAS No.:1073-13-8 MDL No.:MFCD00009695

MF:C8H12O MW:124.1803

89-55-4

3-Amino-2,4-dimethylpyridine

Catalog No.:AA0084TA

CAS No.:1073-21-8 MDL No.:MFCD08235192

MF:C7H10N2 MW:122.1677

89-55-4

2,6-Lutidine-n-oxide

Catalog No.:AA003G31

CAS No.:1073-23-0 MDL No.:MFCD00039715

MF:C7H9NO MW:123.1525

89-55-4

2-Propionylpyrrole

Catalog No.:AA003HTP

CAS No.:1073-26-3 MDL No.:MFCD01696449

MF:C7H9NO MW:123.1525

89-55-4

2-Hydroxythioanisole

Catalog No.:AA003HDD

CAS No.:1073-29-6 MDL No.:MFCD00002211

MF:C7H8OS MW:140.2028

89-55-4

Pyridine,4-chloro-3-methyl-, 1-oxide

Catalog No.:AA007EKY

CAS No.:1073-34-3 MDL No.:MFCD00128858

MF:C6H6ClNO MW:143.5709

89-55-4

4-Bromobenzocyclobutene

Catalog No.:AA0033VJ

CAS No.:1073-39-8 MDL No.:MFCD09029072

MF:C8H7Br MW:183.0452

89-55-4

(1-Bromoethyl)cyclohexane

Catalog No.:AA003BCG

CAS No.:1073-42-3 MDL No.:MFCD12065565

MF:C8H15Br MW:191.1087

89-55-4

6-Methylpyrimidine-4-carbaldehyde

Catalog No.:AA009QTH

CAS No.:1073-53-6 MDL No.:MFCD09881197

MF:C6H6N2O MW:122.1246

89-55-4

2-Pyrimidinamine,4-(methylthio)-

Catalog No.:AA0084N3

CAS No.:1073-54-7 MDL No.:MFCD18816603

MF:C5H7N3S MW:141.1942

89-55-4

(2-Chloroethyl)cyclohexane

Catalog No.:AA007EKF

CAS No.:1073-61-6 MDL No.:MFCD11646261

MF:C8H15Cl MW:146.6577

89-55-4

Benzylhydrazine hydrochloride

Catalog No.:AA003O26

CAS No.:1073-62-7 MDL No.:MFCD01722685

MF:C7H11ClN2 MW:158.6286

89-55-4

Pyrimidine-4-carbaldehyde oxime

Catalog No.:AA0094LI

CAS No.:1073-65-0 MDL No.:MFCD18828136

MF:C5H5N3O MW:123.1127

89-55-4

4-Chlorostyrene

Catalog No.:AA00389I

CAS No.:1073-67-2 MDL No.:MFCD00000632

MF:C8H7Cl MW:138.5942

89-55-4

4-Chlorophenylhydrazine

Catalog No.:AA007W84

CAS No.:1073-69-4 MDL No.:MFCD00038132

MF:C6H7ClN2 MW:142.5862

89-55-4

4-Chlorophenylhydrazine, HCl

Catalog No.:AA003L5B

CAS No.:1073-70-7 MDL No.:MFCD00012943

MF:C6H8Cl2N2 MW:179.0471

89-55-4

4-(Methylthio)phenol

Catalog No.:AA0033R1

CAS No.:1073-72-9 MDL No.:MFCD00002351

MF:C7H8OS MW:140.2028

89-55-4

2-Propanone, 1-(tetrahydro-2-furanyl)-

Catalog No.:AA007EF1

CAS No.:1073-73-0 MDL No.:MFCD12153334

MF:C7H12O2 MW:128.1690

89-55-4

2,6-Dimethyltetrahydro-4h-pyran-4-one

Catalog No.:AA008RZB

CAS No.:1073-79-6 MDL No.:MFCD01693965

MF:C7H12O2 MW:128.1690

89-55-4

1-(3-Bromophenyl)-1h-pyrrole

Catalog No.:AA0084TF

CAS No.:107302-22-7 MDL No.:MFCD02665243

MF:C10H8BrN MW:222.0812

89-55-4

4-(2-fluoro-1-hydroxyethyl)benzonitrile

Catalog No.:AA01DX74

CAS No.:1073056-22-0 MDL No.:MFCD31666888

MF:C9H8FNO MW:165.1643

89-55-4

2-chloro-1-[4-(4-fluorophenyl)piperazin-1-yl]ethan-1-one hydrochloride

Catalog No.:AA019JE6

CAS No.:1073059-28-5 MDL No.:MFCD08445288

MF:C12H15Cl2FN2O MW:293.1647

89-55-4

2-(3,5-Dibromophenyl)-4,6-diphenyl-1,3,5-triazine

Catalog No.:AA00942Z

CAS No.:1073062-59-5 MDL No.:MFCD25562933

MF:C21H13Br2N3 MW:467.1560

89-55-4

(4-bromo-1,5-dimethyl-1H-pyrazol-3-yl)methanol

Catalog No.:AA01BXKL

CAS No.:1073067-93-2 MDL No.:MFCD30497696

MF:C6H9BrN2O MW:205.0525

89-55-4

1,3-dimethyl-2-oxo-1,2-dihydroquinoline-4-carboxylic acid

Catalog No.:AA01CA6T

CAS No.:1073071-78-9 MDL No.:MFCD24499224

MF:C12H11NO3 MW:217.2206