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A New Amphiphilic Brønsted Acid as Catalyst for the Friedel– Crafts Reactions of Indoles in Water

2020-01-15 08:55:40


Yuan Cheng, Xiongyu Ou, Jimei Ma, Linhao Sun, and Zhong-Hua Ma

 

 

Introduction
Using water as a reaction media offers advantages for cost, safety, and environment, and is therefore considered green and ideal for laboratory and industry processes. Hence many efforts have been devoted to the development of aqueous catalytic reactions.[1] In aqueous suspension, some reactions involving organic substrates are accelerated, which has been defined as “on water” reactions by Sharpless.[1b] Several approaches have been aimed to strengthen the interaction of organic substrates under “on water” conditions, including the use of surfactants as amphiphilic additives,[1d,1e] the use of phase-transfer catalysts,[2] and the specifically functionalized design of the catalyst structure.[1e–1g] Water also brings some benefits for product isolation. Various types of reactions forming C-C and C-heteroatom bond have been carried out in water with enhanced reactivity and selectivity, such as the nucleophilic attack of a carbanion species in conjugate addition reaction, known as Michael-type reactions.[1a,1c] For example, a Michael addition of ß,ß-disubsti- tuted nitroalkenes with malonate derivatives was reported by Song, in which the otherwise unreactive substrate systems were demonstrated as on-water catalytic reaction.[1a]

 

An effective promotion for nucleophilic addition is via  the use of Brønsted or Lewis acids to activate electrophiles.[3] How- ever, the activating ability of Brønsted acids is commonly weak- ened in presence of water. A few studies,[4] initiated by Kobaya- shi's pioneering work,[3e] were developed on Brønsted acid-surfactant-combined catalysts and their applications in aqueous systems. The surfactant segments assemble into micelles as microreactor, whose hydrophobic cores trap the labile sub- strates and exclude water molecules,[3b,5] while the micelle exte- rior remains hydrated, and allows the permeation of protons for substrate activation.[6] This surfactant-combined strategy has also been extended to solid Brønsted acids.

 

The hydrophobic assembly is probably caused by fluorocar- bon chain except hydrocarbon chain. Perfluoroalkyl chains have a stronger hydrophobic character than hydrocarbon chains due to their greater molecular cross-sectional area.[7] A classic exam- ple is -C8F17, which is applied in fluorous biphasic media for fluorous catalyst recycling.[8] Even relatively short -C4F9 chains exhibit significant hydrophobicity. Our previous research dem- onstrated that -C4F9 hindered access of water molecules to ad- jacent SO2NHSO2 acid sites,[9] and hydrogen was impeded to bind with the negative  conjugate  base  SO2N–SO2.[10] Similarly, in Wang's reports, pyrrolidine perfluorobutyl sulfonamide was used in aqueous catalysis.[11] On the other hand, perfluoroalkyl sulfonylimides, (RFSO2)2NH, known as nitrogen acids, is widely applied in catalytic field instead of SO3H analogues to practice challenging tasks because of their strong acidity.[3c,3d,9] Gener- ally, compounds with high fluorine content (> 60 %) strongly prefer to go into fluorous phase in fluorocarbon–hydrocarbon systems.[12] These distinct properties could provide water- shielded microenvironments for aqueous reactions. However, too long fluorocarbon chain will inevitably lead to low miscibility of organic and fluorous substrates,  weaken the  interaction  of organic substrates, and increas the cost.


Herein, in the structure of designed sulfonimide catalyst 1a/ 1b, fluorine content and acid density are well balanced by split- ting long  perfluoroalkyl chain into  two relatively  short  perfluoroalkyl chains, attached to respective imide Brønsted acid sites (Scheme 1). This method adjusts fluorine content at relative low level with elevated acid density per molecule. The acidity is examined by using the Hammett acidity function, the 31P NMR shift of Et3P=O probe, and conductance titration. The  binary  acid catalyst has been applied in water to promote the nucleo- philic addition (the Friedel–Crafts reactions). The substrates  used herein were indoles, a widely distributed core structure in nature, and there is a large number of applications of synthetic indoles as pharmaceuticals and agrochemicals.[3a,13] With the  use of 1a, Friedel–Crafts alkylation of indoles in water was easily performed, via 1,4-addition with ß-monosubstituted vinyl ket- ones and condensation with aldehydes, respectively. The prod- ucts are isolated without column chromatography or recrystalli- zation. The aqueous solution containing 1a is recyclable at least three runs. Furthermore, typically poor-reactive ß,ß-disubsti- tuted vinyl ketones were also activated by the strong acidity of the catalyst, giving medium to good product yields.

 

Results and Discussion
Catalyst Design
Compounds 1a/1b comprise two N-H groups, respectively at- tached to perfluoroalkyl groups (Scheme 1). Perfluoroalkyl groups bring some advantages of stabilizing the anionic charge of the conjugate bases due to its electron-withdrawing effect. Furthermore, there is an extensive  delocalization  system  over N, O and phenyl ring, which conspire to increase the propensity of dissociation of N–H bonds, largely improving the intrinsic acidity and decreases the dependence on external solvation.[14] An example is the analogue (CF3SO2)2NH, whose pKa  values  were 2.8, 2.7 and 2.1, respectively in H2O, MeOH,  and DMSO. The values demonstrate the effect of the two factors on high acidity.[15] Compounds 1a/1b is thus reasoned to serve  as  strong acid.

 

1b was given by acidification of 1b·2Na, but decomposed when handled at ca. 55–65 °C to remove the remained solvent; whereas 1a was obtained. The result suggests that a certain linkage in 1b is more susceptible to the intrinsic acidity  at  higher temperature than that in 1a. The most likely linkage is -CONH-, which is possibly decomposed by the  strong  acidity, but stabilized by -C4F9 in 1a. It is inferred that the nonpolar segments, including -C4F9 groups and  phenyl  ring,  aggregate to protect -CONH- group. Especially in the presence of water, due to the hydrophobic hydration effect, the aggregation splits each other's H-bond association of the water molecules near hydrophobic segments, and the bulk water thus hardly en- croaches -CONH- group.[6a,16] The similar aggregation much less efficiently happens to the shorter -CF3 of 1b. 1a is thus a stable amphiphile.

 

A simple Tyndall effect trial was conducted to confirm the formation of the hydrophobic aggregation (Figure 1a). The Tyn- dall effect is often used as a measurement of a colloid, and the intensity of the effect is proportional to the  mean  volume  of the particles. In our trial, obvious Tyndall phenomenon hap- pened to 1a solution, showing the nano-level aggregation ex- isted. As a comparison, no similar phenomenon was observed  for CF3SO3H solution. Furthermore, TEM images of 1a aqueous solution is shown in Figure 1(b). A large amount of nano-size aggregates was observed, with a size of 15–20 nm. Their rela- tively small diameters implied a stacked hydrophobic segment among molecules.


The Acidity Analysis
The acidity of 1a was examined by the Hammett acidity func- tion (H0), Gutmann method, and conductance titration. The re- sults are summarized in Table 1. H0 was obtained by UV/Vis spectrophotometry method, which is a semiquantitative meas- ure of acidity used for concentrated solutions of strong acid.[10] As shown, the H0 value of 1a was –0.52, definitely comparable with tested –0.33 of concentrated H2SO4. The acidity was fur- ther determined by the 31P NMR shift of the Et3P=O probe according to the classical Gutmann method.[10,17] The probe formed Et3P=O···H H-bond with acids. The stronger acidity, the stronger hydrogen bond, and the lower electron density at the phosphorus, and the larger 31P chemical shift. The  chemical  shift difference (Δδ31P) of 1a/Et3P=O adducts to the reference (C6H5)2ClP=O was 46.44, very close to 46.40 of H2SO4/Et3P=O adducts.[10] These results are also supported by the initial con- ductances of 1a and H2SO4 with the  same  concentrations,  which are both 0.136 ms/cm, meaning the close ionization abil- ity   of  1a   and   H2SO4.   The  values   are   obviously  higher than 0.111 ms/cm of oxalic acid. Also, the acid content of 1a is calculated as 2.49 mmol/g (vs. theoretic 2.62 mmol/g) based on the titration curve, suggesting at least 95 % purity of 1a. These results demonstrate 1a can rival the acidity of  concentrated  H2SO4.


Catalytic Michael Addition of Indoles with α,ß-Unsaturated Ketones in Water
Acid-catalyzed Michael addition reactions of indoles with α,ß- unsaturated carbonyl compounds construct 3-substituted ind- oles, a type of important precursors in the synthesis of biologi- cally active compounds and natural products.[18] Our initial at- tempt involved the use of differently active substrates to react with indole 2a, such as vinyl aldehyde (3a), 3-methyl-2-butenal (3b), methyl acrylate (3c), 4-methyl-3-penten-2-one (3d), and 3- penten-2-one (3e), in the presence of 1a. The results are shown in Table 2.


Active 3a and 3b were easily consumed, but no purification was conducted for products 4a and 4b, due to the complex product system based on TLC analysis; while the reaction of poor-reactive ester 3c was sluggish using up to 5.0 mol-% 1a (Entries 1–3). The reaction results of ß,ß-disubstituted vinyl ket- one 3d, which lacks reactivity attributed to the steric and elec- tronic nature of ß-carbon, are given in entries 4–8. Solvent screening demonstrated THF  and  H2O  afforded  comparable  80 % and 78 % yields, superior to other solvents (48–61 %). Wa- ter was thus preferred from the perspective of green chemis- try.[1a,1d] The relatively reactive vinyl ketone 3e furnished com- plex products under the same conditions, and only 6 % yield of 4e was given (Entry 9); whereas, it went up to 62 % at 30 °C  with reduced 2.5 mol-% of 1a (Entry 10). Furthermore,  91 %  yield occurred with the equimolar 2a and 3e (Entry 11).
With the optimized reaction conditions in hand, the general- ity of the catalytic system was explored, and the results  are  listed in Scheme 2. To our delight, the high catalytic perform- ance of 1a was extended to various indoles with high func- tional group tolerance. ß-Monosubstituted vinyl ketones gave 86–98 % yields (4e–4p); while ß, ß-Disubstituted vinyl ketone exhibited 78–85 % yields (4d, 4r–4t) and moderate 42 % yield of 4q.


Various Brønsted acid catalysts were used to catalyze the re- actions to get a mechanistic insight, and the results are summa- rized in Table 3. Keeping loading the same mol of H+ into the system, H2SO4 gave only 8 % and 22 % yields of 4k, in 3 h and  24 h, respectively; while CF3SO3H gave 26 % yield in 3 h (Entries 2–4). Interestingly, the micelle-type acid, o-C12H25C6H4SO3 H,  gave 91 % yield in 2 h (Entry 5). The difference was insignifi- cantly relative to acid strength for ß-monosubstituted vinyl ketone. The acid strength, based on the H0 values, has the fol- lowing order: CF3SO3OH (–3.52) > H2SO4 (–0.33) ≈ 1a (–0.52) >o-C12H25C6H4SO3H (ca. 0.44–0.58).[10] It was thus reasoned that the  hydrophobic  segments  -C12H25  of  o-C12H25C6H4SO3H formed micelles, locating the organic substrates and facilitating the reaction. Contrarily, H2SO4 and CF3SO3H lacked  hydro- phobic segment, giving poor catalytic efficiency. The similar hy- drophobic nano-aggregations were formed in 1a for its amphiphilic structure, leading to 98 % yield of 4k (Entry 1), slightly higher than 91 % by o-C12H25C6H4SO3H. This probably sug- gested less product residual in the nano-aggregations. The nano-aggregations were confirmed by Tyndall effect and TEM image (Figure 1). The fluorine content of 1a comes to 45 %, and the lipophobicity of fluorocarbon chain promoted the separa- tion of the product from the catalyst. Moreover, C4F9- groups   are adjacent to N-H sites, and the hydrophobic  aggregations can control the local polarity around active sites. The controlling allows modulating the activity of catalysts.[1g,9] A homemade acid, Cl(CH2)3SO2NHSO2C4F9, was used to support  the  idea.[10] The acid gave slightly reduced yield (91 %), in which ClCH2CH2CH2- instead of C4F9- led to the fluorine content down to 39 %. Moreover, the product isolation is simple. The aqueous system with 1a allowed obvious oily product floated on  the  face (Figure 2, inset). A simple extraction using EtOAc was enough to offer pure products, without chromatography and recrystallization, which reduced the waste generation.


On the other hand, 1a-catalysed addition of ß,ß-disubsti- tuted vinyl ketone 3d gave 82 % yield, much higher than 36 % by   C12H25C6H4SO3H   and   61 %   by   Cl(CH2)3SO2NHSO2C4F9. 1a and Cl(CH2)3SO2NHSO2C4F9, with more excellent acidity, acti- vated 3d more efficiently than C12H25C6H4SO3H. 1a thus exhib- ited the best catalytic performance.


In our experiments, the use of water as medium improved the reaction  yield and  controlled the  product  solubility,  which simplified the product purification process in the reaction of active ß-monosubstituted substrate. The strong acidity of 1a expanded the substrate scope to the ß,ß-disubstituted ketones, to which o-C12H25C6H4SO3H was not effective due to lower acidity. Furthermore, 1a is a dual Brønsted acid, and the catalyst dosage was less (2.5 mol-% vs. 5 mol-%).
Based on the observations and literatures, a tentative enrich- ment and activation model of α,ß-unsaturated ketone is pro- posed, as depicted in Figure 2. The fluorocarbon chains of 1a tend to regroup and segregate from both the hydrophilic -NH and lipophilic phenyl ring, and aggregate in a separate zone.


Benefiting from its bulkiness, the aggregations stack into a large-size nuclear hydrophobic zone; while the attached -NH sites hang on the outer zone. -NH  groups  form  H-bond  with the carbonyl group of enol ketone or competitive bulky water. However, the fluorocarbon chains, along with phenyl ring, help to resist bulk water, and the organic substrates was thus acti- vated. Moreover, the ethylene linkage of enol ketones possibly get accessible to the phenyl rings. The organic substrate is thus enriched around 1a, facilitating the further reaction.
The recycling performance of 1a was investigated using 2a and 3f  to give 4k, and the results are in Table  4. CCl4 was used  to extract 4k, and the aqueous phase was  fed  with  fresh  2a and 3f for the next run. As shown, the catalyst could be reused  at least three runs with > 92 % yields. The extension of reaction time was possibly owed to slight catalyst loss. In the following cycle, the yield was down to 87 % in 12 h.


Catalytic Condensation of Indoles with Aldehyde in Water
Furthermore, the catalytic generality of 1a in water was investi- gated in condensation of indole with aldehyde. The product 3, 3-bis(indolyl)alkanes (BIAs), which were widely isolated from various natural sources, exhibit a range of biological activi- ties.[13b] The investigations started with 4-anisaldehyde (5a) and 2a in water at 30 °C (Table 5). 2a was consumed completely in  15 minutes in the presence of 2.5 mol-% 1a, but with complex products (Entry 1). A reduced amount of 1a (1 mol-%) produced unsolvable sticky product (Entry 2), but contaminated by resid- ual 2a and 5a. Probably, 1a worked highly efficiently, and BIA precipitated quickly so that the reagents were wrapped in. A trace of organic solvents was thus added (Entries 3, 4). As men- tioned above, the hydrophobic aggregations were loose, and thus water remains in contact with the hydrophobic chain to some degree.[6a] The added organic solvents filled the inter- space, and induced the hydrophobic zone becoming denser. A little CHCl3 or EtOAc (5 %, v: v) was as expected,  and provided  94 % and 91 % yields, respectively. It suggested most of the remained substrate went into the hydrophobic aggregation. EtOH was also used, only producing sticky product very quickly (Entry 5). Yield of 79 % was obtained by column chromatogra- phy in extended 4 h (Entry 6). This was reasonable considering EtOH dispersed over the system because of the  water-solubility.

 

Less toxic EtOAc was used in the exploration experiments of substrate scope. The results are shown in Scheme 3. Simple filtration for powder products or extraction for sticky products were carried out with > 95 % purity, confirmed by NMR spectro- scopy. Excellent yields of 87–99 % were given.
Similarly to above Michael addition, the strong acidity of 1a expanded the catalytic spectrum to the unactived  ketones  in the condensation reactions (Scheme 4). Acetone and butanone gave satisfactory 74–94 % yields (8a–8d, 8f–8i). The strong acidity of 1a successfully activated the aliphatic ketones. Some- what surprising, only moderate yield (42 %) of 4e was obtained. Various Brønsted acid catalysts were also used  to  catalyze the reactions, shown in Table 6.  Under  the  similar  conditions, 1a gave 91 % yield of 6a, 54 % yield for o-C12H25C6H4SO3H and 81 % yield for Cl(CH2)3SO2NHSO2C4F9, but no detectable yield for H2SO4 (Entries 1–4). The formation of hydrophobic location of the catalysts played a crucial role. Additionally, 1a exhibited more excellent catalytic ability than the other two due to its acidity superiority both in the reactions of anisaldehyde and acetone (Entries 5–7).


In our catalytic reactions, the careful purification by column chromatography and recrystallization were not obligated. This   is significant, because synthetic chemistry encourages to reduce the reaction waste. The advantage was attributed to the local hydrophobic effect of the catalyst 1a. The hydrocarbon chain helped to enrich the substrates, and the fluorocarbon chain re- pelled away the excess water molecules and product molecules due to its hydrophobicity/lipophobicity. The waste generated from silica and toxic solvents was thus reduced. This is signifi- cant for searching environmentally benign reactions and reduce the E factor.[1d]

 

Conclusions
In summary, we demonstrated a designed Brønsted acid 1a en- ables Friedel–Crafts alkylation of indoles in water. The hydro- phobic aggregations of fluorocarbon chains, along with phenyl ring, of 1a  protected acid sites from bulk water and enriched  the substrates. The amphiphilic structure has been proven cru- cial for the high catalytic efficiency. The catalyst reasonably re- duces the employment of the fluorocarbon number by splitting the longer fluorocarbon chain into shorter, with strong acidity and hydrophobicity maintained. The strong acidity of 1a enabled the reactions of some unreactive substrates in water.


 

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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

89-55-4

5-(2,4-Dichlorophenyl)pyridin-2-amine

Catalog No.:AA007WFA

CAS No.:1073114-78-9 MDL No.:MFCD16778826

MF:C11H8Cl2N2 MW:239.1006

89-55-4

Methyl 2-chloro-6-(trifluoromethyl)nicotinate

Catalog No.:AA0094OZ

CAS No.:1073129-57-3 MDL No.:MFCD00016047

MF:C8H5ClF3NO2 MW:239.5790

89-55-4

Methyl (1r,2r)-rel-2-aminocyclohexane-1-carboxylate hydrochloride

Catalog No.:AA01DMCO

CAS No.:107313-17-7 MDL No.:MFCD28892334

MF:C16H32Cl2N2O4 MW:387.3423

89-55-4

Benzamide,N-[2-(1H-benzimidazol-2-yl)ethyl]-

Catalog No.:AA007WF8

CAS No.:107313-47-3 MDL No.:MFCD00522697

MF:C16H15N3O MW:265.3098

89-55-4

2-(4-ethylphenyl)-2-[(trimethylsilyl)oxy]acetonitrile

Catalog No.:AA01BA0T

CAS No.:1073135-75-7 MDL No.:MFCD16786523

MF:C13H19NOSi MW:233.3816

89-55-4

Defactinib

Catalog No.:AA008TCN

CAS No.:1073154-85-4 MDL No.:MFCD25977806

MF:C20H21F3N8O3S MW:510.4927

89-55-4

1-(4-chlorophenyl)-2-(piperazin-1-yl)ethan-1-one dihydrochloride

Catalog No.:AA00VT5N

CAS No.:1073155-04-0 MDL No.:MFCD16295341

MF:C12H17Cl3N2O MW:311.6352

89-55-4

N-(3-(Aminomethyl)pyridin-2-yl)-n-methylmethanesulfonamide acetate

Catalog No.:AA0095N9

CAS No.:1073159-75-7 MDL No.:MFCD29044904

MF:C10H17N3O4S MW:275.3247

89-55-4

Defactinib hydrochloride

Catalog No.:AA008TIY

CAS No.:1073160-26-5 MDL No.:MFCD28144730

MF:C20H22ClF3N8O3S MW:546.9537

89-55-4

Methyl 4-bromo-3-(trifluoromethyl)benzoate

Catalog No.:AA0084TC

CAS No.:107317-58-8 MDL No.:MFCD10566409

MF:C9H6BrF3O2 MW:283.0419

89-55-4

Methyl 5-amino-2-chloroisonicotinate

Catalog No.:AA007WF6

CAS No.:1073182-59-8 MDL No.:MFCD11848213

MF:C7H7ClN2O2 MW:186.5957

89-55-4

3-Amino-6-chloro-4-methylpicolinic acid

Catalog No.:AA00HAW9

CAS No.:1073182-76-9 MDL No.:MFCD18382760

MF:C7H7ClN2O2 MW:186.5957

89-55-4

3-Amino-4,6-dichloropicolinonitrile

Catalog No.:AA0098G0

CAS No.:1073182-86-1 MDL No.:MFCD20701019

MF:C6H3Cl2N3 MW:188.0141

89-55-4

3-Amino-4,6-dichloropicolinic acid

Catalog No.:AA009986

CAS No.:1073182-87-2 MDL No.:MFCD24499074

MF:C6H4Cl2N2O2 MW:207.0142

89-55-4

4,4'-Bis[N-(1-naphthyl)-N-phenylamino]-4''-phenyltriphenylamine

Catalog No.:AA003KBP

CAS No.:1073183-32-0 MDL No.:MFCD06797058

MF:C56H41N3 MW:755.9448

89-55-4

tert-Butyl 4-(4-methylbenzoyl)piperazine-1-carboxylate

Catalog No.:AA00HAWC

CAS No.:1073190-54-1 MDL No.:MFCD14635762

MF:C17H24N2O3 MW:304.3841

89-55-4

1-chloro-5-methylhexan-2-ol

Catalog No.:AA01BGMC

CAS No.:107323-80-8 MDL No.:MFCD19232587

MF:C7H15ClO MW:150.6464

89-55-4

2-Benzyloxybenzyl acetate

Catalog No.:AA008WSQ

CAS No.:1073234-31-7 MDL No.:MFCD09038505

MF:C16H16O3 MW:256.2964

89-55-4

trans-1-benzyl-4-phenylpyrrolidin-3-aMine

Catalog No.:AA0095N2

CAS No.:1073263-65-6 MDL No.:MFCD21608504

MF:C17H20N2 MW:252.3541

89-55-4

rac-(3R,4S)-1-benzyl-4-(4-fluorophenyl)pyrrolidin-3-amine, trans

Catalog No.:AA01DX75

CAS No.:1073263-80-5 MDL No.:MFCD21605249

MF:C17H19FN2 MW:270.3446

89-55-4

(1s,4s)-4-(trifluoromethyl)cyclohexan-1-amine

Catalog No.:AA00IMIK

CAS No.:1073266-01-9 MDL No.:MFCD19686543

MF:C7H12F3N MW:167.1721

89-55-4

Trans-4-(trifluoromethyl)cyclohexanamine

Catalog No.:AA008UEV

CAS No.:1073266-02-0 MDL No.:MFCD18914322

MF:C7H12F3N MW:167.1721

89-55-4

(R)-3-tert-Butoxycarbonylamino-4-(1h-indol-3-yl)-butyric acid

Catalog No.:AA0094WR

CAS No.:1073269-91-6 MDL No.:MFCD08276227

MF:C17H22N2O4 MW:318.3676

89-55-4

4,4-diMethyl-2-PyrrolidineMethanol

Catalog No.:AA0092MB

CAS No.:1073283-04-1 MDL No.:MFCD19227423

MF:C7H15NO MW:129.2001

89-55-4

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

Catalog No.:AA008STT

CAS No.:1073312-28-3 MDL No.:MFCD08063077

MF:C11H14BClFNO2 MW:257.4968

89-55-4

(Trimethyl)pentamethylcyclopentadienyltitanium (IV)

Catalog No.:AA003CML

CAS No.:107333-47-1 MDL No.:MFCD00269851

MF:C13H29Ti----- MW:233.2364

89-55-4

5-(Hydroxymethyl)morpholin-3-one

Catalog No.:AA008ZD2

CAS No.:1073338-64-3 MDL No.:MFCD11044094

MF:C5H9NO3 MW:131.1299

89-55-4

5-(Ethoxycarbonyl)furan-2-boronic acid, pinacol ester

Catalog No.:AA003Q8Z

CAS No.:1073338-92-7 MDL No.:MFCD11855980

MF:C13H19BO5 MW:266.0980

89-55-4

3-iodo-5-(trifluoroMethyl)phenol

Catalog No.:AA00953B

CAS No.:1073339-06-6 MDL No.:MFCD12405423

MF:C7H4F3IO MW:288.0057

89-55-4

2,5-Dimethoxyphenylboronic acid, pinacol ester

Catalog No.:AA007EKZ

CAS No.:1073339-07-7 MDL No.:MFCD12405521

MF:C14H21BO4 MW:264.1251

89-55-4

2-(3,4-Bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Catalog No.:AA00944F

CAS No.:1073339-08-8 MDL No.:MFCD12405522

MF:C14H15BF6O2 MW:340.0691

89-55-4

2,3-Methylenedioxyphenylboronic acid pinacol ester

Catalog No.:AA009454

CAS No.:1073339-10-2 MDL No.:MFCD12405524

MF:C13H17BO4 MW:248.0827

89-55-4

5-Bromo-2,3-difluorophenylboronic acid, pinacol ester

Catalog No.:AA003EV1

CAS No.:1073339-12-4 MDL No.:MFCD11855989

MF:C12H14BBrF2O2 MW:318.9502

89-55-4

4-Chloro-2-fluoro-5-(methoxycarbonyl)phenylboronic acid, pinacol ester

Catalog No.:AA0090C8

CAS No.:1073339-13-5 MDL No.:MFCD12026085

MF:C14H17BClFO4 MW:314.5448

89-55-4

2,2'-(4,5,6-Trifluoro-1,3-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Catalog No.:AA00HAWO

CAS No.:1073339-14-6 MDL No.:MFCD12407210

MF:C18H25B2F3O4 MW:384.0059

89-55-4

2,3-Difluorophenylboronic acid pinacol ester

Catalog No.:AA009522

CAS No.:1073339-17-9 MDL No.:MFCD12405347

MF:C12H15BF2O2 MW:240.0541

89-55-4

2-(5-Bromo-2,3,4-trifluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Catalog No.:AA00HAWQ

CAS No.:1073339-18-0 MDL No.:MFCD12405350

MF:C12H13BBrF3O2 MW:336.9406

89-55-4

5-Bromo-2,3,4-trifluorophenol

Catalog No.:AA0094EA

CAS No.:1073339-19-1 MDL No.:MFCD11857741

MF:C6H2BrF3O MW:226.9787

89-55-4

2-Trifluoromethylphenylboronic acid, pinacol ester

Catalog No.:AA008WMN

CAS No.:1073339-21-5 MDL No.:MFCD06795676

MF:C13H16BF3O2 MW:272.0711

89-55-4

2-(4-Methoxythiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Catalog No.:AA009987

CAS No.:1073339-22-6 MDL No.:MFCD12405477

MF:C11H17BO3S MW:240.1269

89-55-4

3-Chloromethylphenylboronic acid pinacol ester

Catalog No.:AA007EKX

CAS No.:1073353-44-2 MDL No.:MFCD11053847

MF:C13H18BClO2 MW:252.5448

89-55-4

N-Methyl-4-benzenesulfonamideboronic acid pinacol ester

Catalog No.:AA007EKW

CAS No.:1073353-47-5 MDL No.:MFCD06657895

MF:C13H20BNO4S MW:297.1782

89-55-4

4-(2-Hydroxyethylcarbamoyl)phenylboronic acid, pinacol ester

Catalog No.:AA007EKU

CAS No.:1073353-51-1 MDL No.:MFCD06795648

MF:C15H22BNO4 MW:291.1505

89-55-4

4-Pyrrolidinylcarbonylphenylboronic acid, pinacol ester

Catalog No.:AA007WF1

CAS No.:1073353-55-5 MDL No.:MFCD09027085

MF:C17H24BNO3 MW:301.1884

89-55-4

4-(N-Benzylaminocarbonyl)phenylboronic acid, pinacol ester

Catalog No.:AA003SOM

CAS No.:1073353-57-7 MDL No.:MFCD09266184

MF:C20H24BNO3 MW:337.2205

89-55-4

4-(N,O-Dimethylhydroxylaminocarbonyl)phenylboronic acid, pinacol ester

Catalog No.:AA003T2P

CAS No.:1073353-58-8 MDL No.:MFCD09953501

MF:C15H22BNO4 MW:291.1505

89-55-4

4-(Furfurylaminocarbonyl)phenylboronic acid, pinacol ester

Catalog No.:AA003K5M

CAS No.:1073353-59-9 MDL No.:MFCD09266168

MF:C18H22BNO4 MW:327.1826

89-55-4

4-(2-Methoxyethylcarbamoyl)phenylboronic acid, pinacol ester

Catalog No.:AA0090CG

CAS No.:1073353-60-2 MDL No.:MFCD09266188

MF:C16H24BNO4 MW:305.1771

89-55-4

3-Pyrrolidinylcarbonylphenylboronic acid, pinacol ester

Catalog No.:AA007WF0

CAS No.:1073353-61-3 MDL No.:MFCD09027086

MF:C17H24BNO3 MW:301.1884

89-55-4

3-(Piperidine-1-carbonyl)phenylboronic acid, pinacol ester

Catalog No.:AA0084T3

CAS No.:1073353-62-4 MDL No.:MFCD09027084

MF:C18H26BNO3 MW:315.2149

89-55-4

3-(Furfurylaminocarbonyl)phenylboronic acid, pinacol ester

Catalog No.:AA003I5J

CAS No.:1073353-63-5 MDL No.:MFCD09266173

MF:C18H22BNO4 MW:327.1826

89-55-4

3-(2-Methoxyethylcarbamoyl)phenylboronic acid, pinacol ester

Catalog No.:AA003HY8

CAS No.:1073353-64-6 MDL No.:MFCD09266187

MF:C16H24BNO4 MW:305.1771

89-55-4

2,4-Bis(trifluoromethyl)phenylboronic acid, pinacol ester

Catalog No.:AA007EKT

CAS No.:1073353-65-7 MDL No.:MFCD09953467

MF:C14H15BF6O2 MW:340.0691

89-55-4

2-Fluoro-4-trifluoromethylphenylboronic acid, pinacol ester

Catalog No.:AA008SFX

CAS No.:1073353-68-0 MDL No.:MFCD08458187

MF:C13H15BF4O2 MW:290.0616

89-55-4

3-Chloro-2-fluoropyridine-4-boronic acid pinacol ester

Catalog No.:AA003J3V

CAS No.:1073353-71-5 MDL No.:MFCD09037476

MF:C11H14BClFNO2 MW:257.4968

89-55-4

1,3-Bis(4-boronophenyl)urea, bispinacol ester

Catalog No.:AA0090D4

CAS No.:1073353-72-6 MDL No.:MFCD09972179

MF:C25H34B2N2O5 MW:464.1699

89-55-4

3-Chloro-2-methoxypyridine-4-boronic acid, pinacol ester

Catalog No.:AA003J4A

CAS No.:1073353-73-7 MDL No.:MFCD06798258

MF:C12H17BClNO3 MW:269.5323

89-55-4

5-Bromo-2-methoxypyridine-3-boronic acid, pinacol ester

Catalog No.:AA008RUV

CAS No.:1073353-75-9 MDL No.:MFCD07781157

MF:C12H17BBrNO3 MW:313.9833

89-55-4

4-Carboxynaphthalene-1-boronic acid, pinacol ester

Catalog No.:AA003JZ3

CAS No.:1073353-77-1 MDL No.:MFCD09972180

MF:C17H19BO4 MW:298.1414

89-55-4

2,3-Dichloropyridine-4-boronic acid, pinacol ester

Catalog No.:AA007WEZ

CAS No.:1073353-78-2 MDL No.:MFCD06798257

MF:C11H14BCl2NO2 MW:273.9514

89-55-4

4-Methoxy-2-nitrophenylboronic acid, pinacol ester

Catalog No.:AA003LJO

CAS No.:1073353-81-7 MDL No.:MFCD10699701

MF:C13H18BNO5 MW:279.0967

89-55-4

6-Chloro-1-methylindole-2-boronic acid, pinacol ester

Catalog No.:AA003N2G

CAS No.:1073353-82-8 MDL No.:MFCD11504964

MF:C15H19BClNO2 MW:291.5809

89-55-4

2-Fluoro-4-nitrophenylboronic acid, pinacol ester

Catalog No.:AA008SR8

CAS No.:1073353-89-5 MDL No.:MFCD09264075

MF:C12H15BFNO4 MW:267.0612

89-55-4

3-((Phenylamino)methyl)phenylboronic acid, pinacol ester

Catalog No.:AA003HW7

CAS No.:1073353-90-8 MDL No.:MFCD09266198

MF:C19H24BNO2 MW:309.2104

89-55-4

3-(2-Bromoethoxy)phenylboronic acid, pinacol ester

Catalog No.:AA0084T1

CAS No.:1073353-91-9 MDL No.:MFCD11044883

MF:C14H20BBrO3 MW:327.0218

89-55-4

3,3'-(Ethane-1,2-diylbis(oxy))bis(3,1-phenylene)diboronic acid, pinacol ester

Catalog No.:AA003I8Q

CAS No.:1073353-94-2 MDL No.:MFCD10699702

MF:C26H36B2O6 MW:466.1824

89-55-4

2,5-Dichloropyridine-4-boronic acid, pinacol ester

Catalog No.:AA007WEY

CAS No.:1073353-98-6 MDL No.:MFCD06798256

MF:C11H14BCl2NO2 MW:273.9514

89-55-4

5-Chloro-2-nitrophenylboronic acid, pinacol ester

Catalog No.:AA007EKS

CAS No.:1073353-99-7 MDL No.:MFCD11053894

MF:C12H15BClNO4 MW:283.5158

89-55-4

4-Boc-Aminopyridine-3-boronic acid, pinacol ester

Catalog No.:AA003UG2

CAS No.:1073354-02-5 MDL No.:MFCD08063074

MF:C16H25BN2O4 MW:320.1917

89-55-4

3-Cyano-2-methoxypyridine-5-boronic acid, pinacol ester

Catalog No.:AA0084T0

CAS No.:1073354-05-8 MDL No.:MFCD11504968

MF:C13H17BN2O3 MW:260.0967

89-55-4

(3-Bromomethyl-4-trifluoromethoxyphenylboronic acid, pinacol ester

Catalog No.:AA003BON

CAS No.:1073354-06-9 MDL No.:MFCD11504969

MF:C14H17BBrF3O3 MW:380.9932

89-55-4

2-(1,3-Dioxolan-2-yl)-1-ethylboronic acid pinacol ester

Catalog No.:AA003EN6

CAS No.:1073354-07-0 MDL No.:MFCD03788722

MF:C11H21BO4 MW:228.0930

89-55-4

N-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pivalamide

Catalog No.:AA00HAWT

CAS No.:1073354-10-5 MDL No.:MFCD05663849

MF:C17H26BNO3 MW:303.2042

89-55-4

2-Formylpyridine-5-boronic acid pinacolate

Catalog No.:AA007WEX

CAS No.:1073354-14-9 MDL No.:MFCD06659508

MF:C12H16BNO3 MW:233.0713