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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1-(6-Chloropyrimidin-4-yl)pyrazole-4-boronic acidCatalog No.:AA003CZ2 CAS No.:1072945-81-3 MDL No.:MFCD09972097 MF:C7H6BClN4O2 MW:224.4121 |
4-(4-Nitrophenoxy)phenylboronic acidCatalog No.:AA0090C5 CAS No.:1072945-82-4 MDL No.:MFCD10699618 MF:C12H10BNO5 MW:259.0225 |
4-(Carboxymethoxy)phenylboronic acidCatalog No.:AA007WLX CAS No.:1072945-84-6 MDL No.:MFCD03425920 MF:C8H9BO5 MW:195.9651 |
2-Acetamido-5-chlorophenylboronic acidCatalog No.:AA003BIM CAS No.:1072945-85-7 MDL No.:MFCD11504839 MF:C8H9BClNO3 MW:213.4260 |
6-(Methoxycarbonyl)pyridine-3-boronic acidCatalog No.:AA007EPL CAS No.:1072945-86-8 MDL No.:MFCD09800559 MF:C7H8BNO4 MW:180.9537 |
1-Methyl-1H-benzoimidazole-6-boronic acidCatalog No.:AA007WLW CAS No.:1072945-87-9 MDL No.:MFCD09972099 MF:C8H9BN2O2 MW:175.9803 |
1-(3-Chlorophenyl)pyrazole-4-boronic acidCatalog No.:AA008SSG CAS No.:1072945-88-0 MDL No.:MFCD09878353 MF:C9H8BClN2O2 MW:222.4360 |
1-(2-Chlorophenyl)pyrazole-4-boronic acidCatalog No.:AA003CRB CAS No.:1072945-91-5 MDL No.:MFCD09972101 MF:C9H8BClN2O2 MW:222.4360 |
1-p-Tolylpyrazole-4-boronic acidCatalog No.:AA00386F CAS No.:1072945-92-6 MDL No.:MFCD09972102 MF:C10H11BN2O2 MW:202.0175 |
3-(4-Nitrophenoxy)phenylboronic acidCatalog No.:AA007EPK CAS No.:1072945-93-7 MDL No.:MFCD09972103 MF:C12H10BNO5 MW:259.0225 |
3-(2-Nitro-4-trifluoromethylphenoxy)phenylboronic acidCatalog No.:AA007WLV CAS No.:1072945-94-8 MDL No.:MFCD09972104 MF:C13H9BF3NO5 MW:327.0205 |
3-(2-Nitrophenoxy)phenylboronic acidCatalog No.:AA007EPJ CAS No.:1072945-95-9 MDL No.:MFCD09972105 MF:C12H10BNO5 MW:259.0225 |
Ethyl (3-boronobenzoylamino)acetateCatalog No.:AA007EPI CAS No.:1072945-97-1 MDL No.:MFCD09878356 MF:C11H14BNO5 MW:251.0436 |
2-Chloro-5-methoxypyridine-4-boronic acidCatalog No.:AA003BK0 CAS No.:1072945-98-2 MDL No.:MFCD09972106 MF:C6H7BClNO3 MW:187.3887 |
4-Cyanopyridine-2-boronic acidCatalog No.:AA003L6T CAS No.:1072946-01-0 MDL No.:MFCD08703250 MF:C6H5BN2O2 MW:147.9271 |
3-(p-Tolylcarbamoyl)phenylboronic acidCatalog No.:AA003I78 CAS No.:1072946-03-2 MDL No.:MFCD10699620 MF:C14H14BNO3 MW:255.0769 |
N-(3-Chloro-4-fluorophenyl) 3-boronobenzamideCatalog No.:AA003BN6 CAS No.:1072946-04-3 MDL No.:MFCD09972110 MF:C13H10BClFNO3 MW:293.4858 |
3-Boronoisonicotinic acidCatalog No.:AA003IWD CAS No.:1072946-05-4 MDL No.:MFCD10696649 MF:C6H6BNO4 MW:166.9271 |
3-(3-Isopropylthioureido)phenylboronic acidCatalog No.:AA0090CS CAS No.:1072946-07-6 MDL No.:MFCD09972112 MF:C10H15BN2O2S MW:238.1143 |
Ethyl (4-boronobenzoylamino)acetateCatalog No.:AA003BR1 CAS No.:1072946-08-7 MDL No.:MFCD09972113 MF:C11H14BNO5 MW:251.0436 |
4-Fluoro-2,5-dimethylphenylboronic acidCatalog No.:AA007WLG CAS No.:1072946-10-1 MDL No.:MFCD10699621 MF:C8H10BFO2 MW:167.9732 |
3-Fluoro-4-(4-methoxybenzylthio)phenylboronic acidCatalog No.:AA007WLF CAS No.:1072946-13-4 MDL No.:MFCD10699622 MF:C14H14BFO3S MW:292.1336 |
4-(2-Cyanovinyl)phenylboronic acidCatalog No.:AA0084ZC CAS No.:1072946-14-5 MDL No.:MFCD09972115 MF:C9H8BNO2 MW:172.9763 |
N-(3,4-Difluorophenyl) 3-boronobenzamideCatalog No.:AA0090CA CAS No.:1072946-15-6 MDL No.:MFCD09972116 MF:C13H10BF2NO3 MW:277.0312 |
4-(Methylsulfonyl)-2-(trifluoromethyl)phenylboronic acidCatalog No.:AA0037XX CAS No.:1072946-16-7 MDL No.:MFCD10699623 MF:C8H8BF3O4S MW:268.0179 |
3-(3-Methylthioureido)phenylboronic acidCatalog No.:AA0090BX CAS No.:1072946-17-8 MDL No.:MFCD09972118 MF:C8H11BN2O2S MW:210.0611 |
4-(3-Methylthioureido)phenylboronic acidCatalog No.:AA007WLE CAS No.:1072946-18-9 MDL No.:MFCD10699624 MF:C8H11BN2O2S MW:210.0611 |
2-Chloro-4-methoxypyridine-3-boronic acidCatalog No.:AA003BJY CAS No.:1072946-19-0 MDL No.:MFCD09972119 MF:C6H7BClNO3 MW:187.3887 |
6-(4-Methoxybenzylcarbamoyl)pyridine-3-boronic acidCatalog No.:AA0084ZB CAS No.:1072946-22-5 MDL No.:MFCD10699628 MF:C14H15BN2O4 MW:286.0909 |
Monolithium 4-methoxypyridine-3-boronateCatalog No.:AA003S2V CAS No.:1072946-24-7 MDL No.:MFCD10699631 MF:C6H7BLiNO3 MW:158.8767 |
2-Chloro-6-methoxypyridine-3-boronic acidCatalog No.:AA008SRM CAS No.:1072946-25-8 MDL No.:MFCD11053826 MF:C6H7BClNO3 MW:187.3887 |
2-Chloro-5-methoxypyridine-3-boronic acidCatalog No.:AA007WLD CAS No.:1072946-26-9 MDL No.:MFCD10699632 MF:C6H7BClNO3 MW:187.3887 |
3-(Diethylcarbamoyl)-2-fluorophenylboronic acidCatalog No.:AA007WLC CAS No.:1072946-28-1 MDL No.:MFCD10699633 MF:C11H15BFNO3 MW:239.0511 |
4-(1-BOC-piperidin-4-yloxy)-2-methoxyphenylboronic acidCatalog No.:AA003JV5 CAS No.:1072946-29-2 MDL No.:MFCD10699635 MF:C17H26BNO6 MW:351.2024 |
4-(1-BOC-piperidin-4-yloxy)-3-methoxyphenylboronic acidCatalog No.:AA003JV6 CAS No.:1072946-30-5 MDL No.:MFCD10699636 MF:C17H26BNO6 MW:351.2024 |
4-Pentylcyclohex-1-enylboronic acidCatalog No.:AA003BTU CAS No.:1072946-31-6 MDL No.:MFCD10699637 MF:C11H21BO2 MW:196.0942 |
5-Chloro-2-methyl-4-(trifluoromethyl)phenylboronic acidCatalog No.:AA003MKK CAS No.:1072946-33-8 MDL No.:MFCD11053801 MF:C8H7BClF3O2 MW:238.3992 |
3,4,5-Trichloro-2-methylphenylboronic acidCatalog No.:AA003IBK CAS No.:1072946-34-9 MDL No.:MFCD11053802 MF:C7H6BCl3O2 MW:239.2913 |
4-Boronophthalic acidCatalog No.:AA00386E CAS No.:1072946-35-0 MDL No.:MFCD11053803 MF:C8H7BO6 MW:209.9486 |
2,6-Dichloro-3-nitrophenylboronic acidCatalog No.:AA007EPD CAS No.:1072946-37-2 MDL No.:MFCD10699640 MF:C6H4BCl2NO4 MW:235.8173 |
2,3,4-Trichloro-5-nitrophenylboronic acidCatalog No.:AA003FB9 CAS No.:1072946-38-3 MDL No.:MFCD11053804 MF:C6H3BCl3NO4 MW:270.2623 |
2,6-Dichlorobenzylboronic acidCatalog No.:AA003BIC CAS No.:1072946-39-4 MDL No.:MFCD11053805 MF:C7H7BCl2O2 MW:204.8463 |
4-(1,3-Dioxolan-2-yl)-2,6-difluorophenylboronic acidCatalog No.:AA00386D CAS No.:1072946-41-8 MDL No.:MFCD11053806 MF:C9H9BF2O4 MW:229.9732 |
4-(Aminomethyl)-3-fluorophenylboronic acid, HClCatalog No.:AA008SR6 CAS No.:1072946-45-2 MDL No.:MFCD11053810 MF:C7H10BClFNO2 MW:205.4222 |
5-(Aminomethyl)-2-fluorophenylboronic acid, HClCatalog No.:AA007EPC CAS No.:1072946-46-3 MDL No.:MFCD11053811 MF:C7H10BClFNO2 MW:205.4222 |
5-((Boc-Amino)methyl)furan-2-boronic acidCatalog No.:AA003BUP CAS No.:1072946-49-6 MDL No.:MFCD11053783 MF:C10H16BNO5 MW:241.0487 |
6-Chloro-2-methoxypyridine-3-boronic acidCatalog No.:AA0084ZA CAS No.:1072946-50-9 MDL No.:MFCD11053817 MF:C6H7BClNO3 MW:187.3887 |
3-(1,3-Dioxolan-2-yl)-5-(trifluoromethyl)phenylboronic acidCatalog No.:AA003BNA CAS No.:1072946-51-0 MDL No.:MFCD00008782 MF:C10H10BF3O4 MW:261.9902 |
2-(Bromomethyl)-3,4,5-trichlorophenylboronic acidCatalog No.:AA003BHA CAS No.:1072946-53-2 MDL No.:MFCD11053838 MF:C7H5BBrCl3O2 MW:318.1874 |
3-(2-(Piperidin-1-yl)ethylcarbamoyl)phenylboronic acidCatalog No.:AA007WLA CAS No.:1072946-54-3 MDL No.:MFCD11053842 MF:C14H21BN2O3 MW:276.1391 |
5-(3-Boronophenyl)pentanoic acidCatalog No.:AA003M1N CAS No.:1072946-56-5 MDL No.:MFCD11053844 MF:C11H15BO4 MW:222.0454 |
3-(4-Carboethoxybutyl)phenylboronic acidCatalog No.:AA003BNB CAS No.:1072946-57-6 MDL No.:MFCD11053845 MF:C13H19BO4 MW:250.0986 |
2-Ethoxypyridine-4-boronic acidCatalog No.:AA003H3V CAS No.:1072946-58-7 MDL No.:MFCD07374989 MF:C7H10BNO3 MW:166.9702 |
2-Carboxypyridine-4-boronic acidCatalog No.:AA003KRM CAS No.:1072946-59-8 MDL No.:MFCD11504842 MF:C6H6BNO4 MW:166.9271 |
1-(4-Carboxybutyl)indole-5-boronic acidCatalog No.:AA003M3N CAS No.:1072946-60-1 MDL No.:MFCD11053846 MF:C13H16BNO4 MW:261.0814 |
3-(4-Carboxybutoxy)-2,4,6-trifluorophenylboronic acidCatalog No.:AA003I10 CAS No.:1072946-61-2 MDL No.:MFCD11504843 MF:C11H12BF3O5 MW:292.0162 |
2-Chloro-3-fluoropyridine-5-boronic acidCatalog No.:AA003BW3 CAS No.:1072946-66-7 MDL No.:MFCD04112500 MF:C5H4BClFNO2 MW:175.3532 |
2,4,6-Trifluoro-3-hydroxyphenylboronic acidCatalog No.:AA003BHY CAS No.:1072951-37-1 MDL No.:MFCD11053885 MF:C6H4BF3O3 MW:191.9004 |
5-(BOC-Aminomethyl)thiophene-2-boronic acidCatalog No.:AA00389P CAS No.:1072951-39-3 MDL No.:MFCD11504845 MF:C10H16BNO4S MW:257.1143 |
2-Fluoro-5-(morpholine-4-carbonyl)phenylboronic acidCatalog No.:AA003BKC CAS No.:1072951-41-7 MDL No.:MFCD11504847 MF:C11H13BFNO4 MW:253.0346 |
2-(Methoxycarbonyl)-4-(trifluoromethyl)phenylboronic acidCatalog No.:AA003BHE CAS No.:1072951-42-8 MDL No.:MFCD11504848 MF:C9H8BF3O4 MW:247.9636 |
2-Bromo-5-fluoropyridine-4-boronic acidCatalog No.:AA007EPA CAS No.:1072951-43-9 MDL No.:MFCD04973353 MF:C5H4BBrFNO2 MW:219.8042 |
6-Fluoroquinoline-8-boronic acidCatalog No.:AA003BW6 CAS No.:1072951-44-0 MDL No.:MFCD11504849 MF:C9H7BFNO2 MW:190.9668 |
5-Fluoroquinoline-8-boronic acidCatalog No.:AA003BVA CAS No.:1072951-45-1 MDL No.:MFCD11504850 MF:C9H7BFNO2 MW:190.9668 |
8-Trifluoromethoxyquinoline-5-boronic acidCatalog No.:AA007EP9 CAS No.:1072951-46-2 MDL No.:MFCD11504851 MF:C10H7BF3NO3 MW:256.9737 |
8-Trifluoromethylquinoline-6-boronic acidCatalog No.:AA007WL9 CAS No.:1072951-47-3 MDL No.:MFCD11504852 MF:C10H7BF3NO2 MW:240.9743 |
3-Bromo-5-(trifluoromethoxy)phenylboronic acidCatalog No.:AA007EP8 CAS No.:1072951-48-4 MDL No.:MFCD11504853 MF:C7H5BBrF3O3 MW:284.8230 |
2-Hydroxy-4-trifluoromethylphenylboronic acidCatalog No.:AA0084Z9 CAS No.:1072951-50-8 MDL No.:MFCD03094996 MF:C7H6BF3O3 MW:205.9269 |
3,4-Bis(methoxycarbonyl)phenylboronic acidCatalog No.:AA0084Z8 CAS No.:1072951-51-9 MDL No.:MFCD11504854 MF:C10H11BO6 MW:238.0017 |
2-Fluoro-5-pentanoylphenylboronic acidCatalog No.:AA003BKF CAS No.:1072951-52-0 MDL No.:MFCD11504855 MF:C11H14BFO3 MW:224.0365 |
2,6-Dichloropyridine-4-boronic acidCatalog No.:AA008XCV CAS No.:1072951-54-2 MDL No.:MFCD09751352 MF:C5H4BCl2NO2 MW:191.8078 |
5-Trifluoromethylquinoline-8-boronic acidCatalog No.:AA003BUR CAS No.:1072951-55-3 MDL No.:MFCD11504856 MF:C10H7BF3NO2 MW:240.9743 |
5-Bromo-2-trifluoromethoxyphenylboronic acidCatalog No.:AA0090CK CAS No.:1072951-56-4 MDL No.:MFCD11504857 MF:C7H5BBrF3O3 MW:284.8230 |
4-[(2-Isopropyl-5-methylphenoxy)methyl]phenylboronic acidCatalog No.:AA007WFI CAS No.:1072951-58-6 MDL No.:MFCD08276834 MF:C17H21BO3 MW:284.1578 |
3,5-Diiodo-2-methoxyphenylboronic acidCatalog No.:AA003IKQ CAS No.:1072951-59-7 MDL No.:MFCD08457647 MF:C7H7BI2O3 MW:403.7486 |
2-((3-(Trifluoromethyl)phenoxy)methyl)phenylboronic acidCatalog No.:AA0084Z7 CAS No.:1072951-60-0 MDL No.:MFCD09038421 MF:C14H12BF3O3 MW:296.0495 |
3-(3'-Fluorobenzyloxy)phenylboronic acidCatalog No.:AA003BN7 CAS No.:1072951-62-2 MDL No.:MFCD08276822 MF:C13H12BFO3 MW:246.0420 |
2-[(2',6'-Diisopropylphenoxy)methyl]phenylboronic acidCatalog No.:AA003G4V CAS No.:1072951-64-4 MDL No.:MFCD08705265 MF:C19H25BO3 MW:312.2110 |
2-[(4'-Chloro-1-naphthyloxy)methyl]phenylboronic acidCatalog No.:AA003G55 CAS No.:1072951-65-5 MDL No.:MFCD08705266 MF:C17H14BClO3 MW:312.5553 |
4-[(4-tert-Butyl-2-methylphenoxy)methyl]phenylboronic acidCatalog No.:AA007EP7 CAS No.:1072951-67-7 MDL No.:MFCD09265139 MF:C18H23BO3 MW:298.1844 |
3-[(2'-Isopropyl-5'-methylphenoxy)methyl]phenylboronic acidCatalog No.:AA003IOK CAS No.:1072951-74-6 MDL No.:MFCD22200781 MF:C17H21BO3 MW:284.1578 |
2-[(4'-tert-Butyl-2'-methylphenoxy)methyl]phenylboronic acidCatalog No.:AA003G5A CAS No.:1072951-76-8 MDL No.:MFCD08276830 MF:C18H23BO3 MW:298.1844 |
4-(2'-Fluorobenzyloxy)phenylboronic acidCatalog No.:AA003BR2 CAS No.:1072951-78-0 MDL No.:MFCD08705274 MF:C13H12BFO3 MW:246.0420 |
4-(4'-Isopentyloxyphenyl)phenylboronic acidCatalog No.:AA003BRA CAS No.:1072951-81-5 MDL No.:MFCD08276971 MF:C17H21BO3 MW:284.1578 |
3,5-Dibromo-2-fluorophenylboronic acidCatalog No.:AA003BNQ CAS No.:1072951-82-6 MDL No.:MFCD08276977 MF:C6H4BBr2FO2 MW:297.7122 |
3-Bromo-5-butoxyphenylboronic acidCatalog No.:AA003BOJ CAS No.:1072951-84-8 MDL No.:MFCD08457637 MF:C10H14BBrO3 MW:272.9314 |
6-Bromo-2-fluoro-3-propoxyphenylboronic acidCatalog No.:AA003N14 CAS No.:1072951-85-9 MDL No.:MFCD09038422 MF:C9H11BBrFO3 MW:276.8952 |
3-Bromo-2-isopropoxy-5-formylphenylboronic acidCatalog No.:AA003IXT CAS No.:1072951-86-0 MDL No.:MFCD09750471 MF:C10H12BBrO4 MW:286.9149 |
2-[(2-Isopropyl-5-methylphenoxy)methyl]phenylboronic acidCatalog No.:AA003G4X CAS No.:1072951-87-1 MDL No.:MFCD08276821 MF:C17H21BO3 MW:284.1578 |
6-Bromo-3-butoxy-2-fluorophenylboronic acidCatalog No.:AA003N1B CAS No.:1072951-88-2 MDL No.:MFCD08276825 MF:C10H13BBrFO3 MW:290.9218 |
3-(4-Methoxybenzyloxy)phenylboronic acidCatalog No.:AA0084TO CAS No.:1072951-89-3 MDL No.:MFCD09038416 MF:C14H15BO4 MW:258.0775 |
3-[(4-Chloro-3-methylphenoxy)methyl]phenylboronic acidCatalog No.:AA003ION CAS No.:1072951-91-7 MDL No.:MFCD09265140 MF:C14H14BClO3 MW:276.5232 |
3,5-Dimethyl-4-(3',5'-dimethoxybenzyloxy)phenylboronic acidCatalog No.:AA007EP6 CAS No.:1072951-94-0 MDL No.:MFCD22421632 MF:C17H21BO5 MW:316.1566 |
2-Bromo-3-butoxy-6-fluorophenylboronic acidCatalog No.:AA003GJT CAS No.:1072951-95-1 MDL No.:MFCD08276824 MF:C10H13BBrFO3 MW:290.9218 |
4-(3'-Fluorobenzyloxy)phenylboronic acidCatalog No.:AA003JYC CAS No.:1072951-98-4 MDL No.:MFCD00010512 MF:C13H12BFO3 MW:246.0420 |
3-Formyl-4-isopropoxyphenylboronic acidCatalog No.:AA003BPN CAS No.:1072952-00-1 MDL No.:MFCD08705272 MF:C10H13BO4 MW:208.0188 |
3-(2'-Methoxybenzyloxy)phenylboronic acidCatalog No.:AA0084TN CAS No.:1072952-02-3 MDL No.:MFCD08276833 MF:C14H15BO4 MW:258.0775 |
3-(4'-Fluorobenzyloxy)phenylboronic acidCatalog No.:AA003I06 CAS No.:1072952-03-4 MDL No.:MFCD08705238 MF:C13H12BFO3 MW:246.0420 |
3-Ethylsulfinylphenylboronic acidCatalog No.:AA003BND CAS No.:1072952-07-8 MDL No.:MFCD03092933 MF:C8H11BO3S MW:198.0471 |
3-Carboxy-2-fluorophenylboronic acidCatalog No.:AA007EP5 CAS No.:1072952-09-0 MDL No.:MFCD03095128 MF:C7H6BFO4 MW:183.9295 |
2-Ethylsulfinylphenylboronic acidCatalog No.:AA0084TM CAS No.:1072952-11-4 MDL No.:MFCD03095262 MF:C8H11BO3S MW:198.0471 |
2-Amino-4,5-difluorophenylboronic acidCatalog No.:AA003BIP CAS No.:1072952-14-7 MDL No.:MFCD03095340 MF:C6H6BF2NO2 MW:172.9251 |
5-Hexenylboronic acidCatalog No.:AA003QSK CAS No.:1072952-16-9 MDL No.:MFCD10567048 MF:C6H13BO2 MW:127.9772 |
5-Chloro-2-fluoro-4-methoxyphenylboronic acidCatalog No.:AA007EP3 CAS No.:1072952-18-1 MDL No.:MFCD04112552 MF:C7H7BClFO3 MW:204.3911 |
2-Isopropoxy-4-trifluoromethylphenylboronic acidCatalog No.:AA007WFG CAS No.:1072952-21-6 MDL No.:MFCD04972374 MF:C10H12BF3O3 MW:248.0067 |
2-Boronofuran-3-carboxylic acidCatalog No.:AA0084TK CAS No.:1072952-23-8 MDL No.:MFCD06203510 MF:C5H5BO5 MW:155.9012 |
2-Fluoro-5-hydroxymethylphenylboronic acidCatalog No.:AA007WFF CAS No.:1072952-25-0 MDL No.:MFCD06656276 MF:C7H8BFO3 MW:169.9460 |
2,6-Difluoropyridine-3-boronic acid hydrateCatalog No.:AA003BIF CAS No.:1072952-27-2 MDL No.:MFCD06657881 MF:C5H6BF2NO3 MW:176.9138 |
5-Formyl-3-methylthiophene-2-boronic acidCatalog No.:AA003BVB CAS No.:1072952-28-3 MDL No.:MFCD06657888 MF:C6H7BO3S MW:169.9940 |
2-Picoline-5-boronic acid hydrateCatalog No.:AA008SSJ CAS No.:1072952-30-7 MDL No.:MFCD06657901 MF:C6H10BNO3 MW:154.9595 |
2-Picoline-3-boronic acid HClCatalog No.:AA0033CQ CAS No.:1072952-34-1 MDL No.:MFCD06659489 MF:C6H9BClNO2 MW:173.4052 |
3-Picoline-4-boronic acid HClCatalog No.:AA003BQ3 CAS No.:1072952-40-9 MDL No.:MFCD06659519 MF:C6H9BClNO2 MW:173.4052 |
5-Chloro-2-fluoro-4-methylphenylboronic acidCatalog No.:AA0084TJ CAS No.:1072952-42-1 MDL No.:MFCD07368241 MF:C7H7BClFO2 MW:188.3917 |
5-Hydroxy-2-methoxyphenylboronic acidCatalog No.:AA003NVO CAS No.:1072952-43-2 MDL No.:MFCD07368831 MF:C7H9BO4 MW:167.9550 |
3-Fluoro-5-methylpyridine-4-boronic acidCatalog No.:AA003BPJ CAS No.:1072952-44-3 MDL No.:MFCD07368843 MF:C6H7BFNO2 MW:154.9347 |
2-Fluoro-5-methylpyridine-3-boronic acidCatalog No.:AA003BKD CAS No.:1072952-45-4 MDL No.:MFCD07368857 MF:C6H7BFNO2 MW:154.9347 |
2-Bromo-5-methoxypyridine-4-boronic acidCatalog No.:AA003BJ3 CAS No.:1072952-48-7 MDL No.:MFCD07781222 MF:C6H7BBrNO3 MW:231.8397 |
(4,5-Dimethoxy-2-(methoxycarbonyl)phenyl)boronic acidCatalog No.:AA007WFD CAS No.:1072952-49-8 MDL No.:MFCD07781232 MF:C10H13BO6 MW:240.0176 |
2-Fluoro-3-(ethoxycarbonyl)phenylboronic acidCatalog No.:AA0084TH CAS No.:1072952-52-3 MDL No.:MFCD08064050 MF:C9H10BFO4 MW:211.9827 |
3-Chloro-4-formylphenylboronic acidCatalog No.:AA007EP1 CAS No.:1072952-53-4 MDL No.:MFCD08274473 MF:C7H6BClO3 MW:184.3847 |
BenzovindiflupyrCatalog No.:AA01DZFR CAS No.:1072957-71-1 MDL No.:MFCD30725523 MF:C18H15Cl2F2N3O MW:398.2340 |
Sr-3677Catalog No.:AA008RLJ CAS No.:1072959-67-1 MDL No.:MFCD16619390 MF:C22H24N4O4 MW:408.4504 |
1-Ethyl-1h-pyrazol-5-olCatalog No.:AA007EOZ CAS No.:107296-34-4 MDL No.:MFCD13151912 MF:C5H8N2O MW:112.1298 |
4-(6-Methyl-4,8-dioxo-1,3,6,2-dioxazaborocan-2-yl)benzaldehydeCatalog No.:AA01FGJ9 CAS No.:1072960-66-7 MDL No.:MFCD11215233 MF:C12H12BNO5 MW:261.0384 |
2-(4-Hydroxymethylphenyl)-2,3-dihydro-1h-naphtho[1,8-de][1,3,2]diazaborinineCatalog No.:AA00HAW4 CAS No.:1072960-84-9 MDL No.:MFCD20527131 MF:C17H15BN2O MW:274.1248 |
Cyclopropaneaceticacid, 2-methylene-Catalog No.:AA0084TG CAS No.:1073-00-3 MDL No.:MFCD11558999 MF:C6H8O2 MW:112.1265 |
1,3,2-dioxathiane-2,2-dioneCatalog No.:AA00HAW5 CAS No.:1073-05-8 MDL No.:MFCD00801144 MF:C3H6O4S MW:138.1423 |
1-Bromo-3-fluorobenzeneCatalog No.:AA0032MW CAS No.:1073-06-9 MDL No.:MFCD00000326 MF:C6H4BrF MW:174.9984 |
4,4-Dimethylcyclohex-2-enoneCatalog No.:AA008RLW CAS No.:1073-13-8 MDL No.:MFCD00009695 MF:C8H12O MW:124.1803 |
3-Amino-2,4-dimethylpyridineCatalog No.:AA0084TA CAS No.:1073-21-8 MDL No.:MFCD08235192 MF:C7H10N2 MW:122.1677 |
2,6-Lutidine-n-oxideCatalog No.:AA003G31 CAS No.:1073-23-0 MDL No.:MFCD00039715 MF:C7H9NO MW:123.1525 |
2-PropionylpyrroleCatalog No.:AA003HTP CAS No.:1073-26-3 MDL No.:MFCD01696449 MF:C7H9NO MW:123.1525 |
2-HydroxythioanisoleCatalog No.:AA003HDD CAS No.:1073-29-6 MDL No.:MFCD00002211 MF:C7H8OS MW:140.2028 |
Pyridine,4-chloro-3-methyl-, 1-oxideCatalog No.:AA007EKY CAS No.:1073-34-3 MDL No.:MFCD00128858 MF:C6H6ClNO MW:143.5709 |
4-BromobenzocyclobuteneCatalog No.:AA0033VJ CAS No.:1073-39-8 MDL No.:MFCD09029072 MF:C8H7Br MW:183.0452 |
(1-Bromoethyl)cyclohexaneCatalog No.:AA003BCG CAS No.:1073-42-3 MDL No.:MFCD12065565 MF:C8H15Br MW:191.1087 |
6-Methylpyrimidine-4-carbaldehydeCatalog No.:AA009QTH CAS No.:1073-53-6 MDL No.:MFCD09881197 MF:C6H6N2O MW:122.1246 |
2-Pyrimidinamine,4-(methylthio)-Catalog No.:AA0084N3 CAS No.:1073-54-7 MDL No.:MFCD18816603 MF:C5H7N3S MW:141.1942 |
(2-Chloroethyl)cyclohexaneCatalog No.:AA007EKF CAS No.:1073-61-6 MDL No.:MFCD11646261 MF:C8H15Cl MW:146.6577 |
Benzylhydrazine hydrochlorideCatalog No.:AA003O26 CAS No.:1073-62-7 MDL No.:MFCD01722685 MF:C7H11ClN2 MW:158.6286 |
Pyrimidine-4-carbaldehyde oximeCatalog No.:AA0094LI CAS No.:1073-65-0 MDL No.:MFCD18828136 MF:C5H5N3O MW:123.1127 |
4-ChlorostyreneCatalog No.:AA00389I CAS No.:1073-67-2 MDL No.:MFCD00000632 MF:C8H7Cl MW:138.5942 |
4-ChlorophenylhydrazineCatalog No.:AA007W84 CAS No.:1073-69-4 MDL No.:MFCD00038132 MF:C6H7ClN2 MW:142.5862 |
4-Chlorophenylhydrazine, HClCatalog No.:AA003L5B CAS No.:1073-70-7 MDL No.:MFCD00012943 MF:C6H8Cl2N2 MW:179.0471 |
4-(Methylthio)phenolCatalog No.:AA0033R1 CAS No.:1073-72-9 MDL No.:MFCD00002351 MF:C7H8OS MW:140.2028 |
2-Propanone, 1-(tetrahydro-2-furanyl)-Catalog No.:AA007EF1 CAS No.:1073-73-0 MDL No.:MFCD12153334 MF:C7H12O2 MW:128.1690 |
2,6-Dimethyltetrahydro-4h-pyran-4-oneCatalog No.:AA008RZB CAS No.:1073-79-6 MDL No.:MFCD01693965 MF:C7H12O2 MW:128.1690 |
1-(3-Bromophenyl)-1h-pyrroleCatalog No.:AA0084TF CAS No.:107302-22-7 MDL No.:MFCD02665243 MF:C10H8BrN MW:222.0812 |
4-(2-fluoro-1-hydroxyethyl)benzonitrileCatalog No.:AA01DX74 CAS No.:1073056-22-0 MDL No.:MFCD31666888 MF:C9H8FNO MW:165.1643 |
2-chloro-1-[4-(4-fluorophenyl)piperazin-1-yl]ethan-1-one hydrochlorideCatalog No.:AA019JE6 CAS No.:1073059-28-5 MDL No.:MFCD08445288 MF:C12H15Cl2FN2O MW:293.1647 |
2-(3,5-Dibromophenyl)-4,6-diphenyl-1,3,5-triazineCatalog No.:AA00942Z CAS No.:1073062-59-5 MDL No.:MFCD25562933 MF:C21H13Br2N3 MW:467.1560 |
(4-bromo-1,5-dimethyl-1H-pyrazol-3-yl)methanolCatalog No.:AA01BXKL CAS No.:1073067-93-2 MDL No.:MFCD30497696 MF:C6H9BrN2O MW:205.0525 |
1,3-dimethyl-2-oxo-1,2-dihydroquinoline-4-carboxylic acidCatalog No.:AA01CA6T CAS No.:1073071-78-9 MDL No.:MFCD24499224 MF:C12H11NO3 MW:217.2206 |