43195-94-4

Basic information

• Product Name: [R,(-)]-Chlorophenylacetic acid
• Synonyms: (R)-Phenylchloroacetic acid;(R)-α-Chlorobenzeneacetic acid;[R,(-)]-2-Chloro-2-phenylacetic acid;[R,(-)]-Chlorophenylacetic acid
• CAS NO: 43195-94-4
• Molecular Formula: C₈H₇ClO₂
• Molecular Weight: 170.59
• Mol File: 43195-94-4.mol

Chemical Properties

• Boiling Point: 282.0±20.0 °C(Predicted)
• Appearance: /
• Density: 1.322±0.06 g/cm3(Predicted)
• PKA: 2.40±0.10(Predicted)
• CAS DataBase Reference: [R,(-)]-Chlorophenylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: [R,(-)]-Chlorophenylacetic acid(43195-94-4)
• EPA Substance Registry System: [R,(-)]-Chlorophenylacetic acid(43195-94-4)

Safety Data

• Hazardous Substances Data: 43195-94-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
[R,(-)]-Chlorophenylacetic acid is used as a precursor in the synthesis of various pharmaceuticals. Its role in creating essential medications makes it a crucial component in this industry.
Used in Agrochemical Industry:
[R,(-)]-Chlorophenylacetic acid also serves as a starting material for the production of agrochemicals, which are vital for enhancing crop protection and yield.
Used in Dye Manufacturing:
[R,(-)]-Chlorophenylacetic acid is utilized in the manufacturing of dyes, contributing to the vibrant colors in various products.
Used in Organic Compound Synthesis:
[R,(-)]-Chlorophenylacetic acid is also employed in the synthesis of other organic compounds, highlighting its versatility in chemical reactions.
Used in Anti-Inflammatory and Anti-Cancer Applications:
[R,(-)]-Chlorophenylacetic acid has been studied for its potential biological activity, including anti-inflammatory and anti-cancer properties. It holds promise for the development of treatments for various conditions.
Used in Dermatological Treatments:
[R,(-)]-Chlorophenylacetic acid has been investigated for its use in treating skin conditions such as eczema and psoriasis, potentially offering relief and improved quality of life for those affected by these disorders.

Upstream product

• 102-96-5 (2-nitroethenyl)benzene 
• 611-71-2 MANDELIC ACID 
• 10606-73-2 ethyl 2-chloro-2-phenylacetate 
• 464-43-7 d-borneol 
• 7476-66-6 methyl 2-chloro-2-phenylethanoate 
• 22060-02-2 β-Chlor-ethylphenylchloracetat 
• 22259-83-2 2-chloro-2-phenylacetonitrile 
• 611-71-2 (R)-Mandelic Acid 
• 1355255-19-4 (+/-)-3-(2-chloro-2-phenylacetyl)oxazolidin-2-one 
• 4870-65-9 2-bromophenylacetic acid 
• 103-82-2 phenylacetic acid 
• 2912-62-1 α-chlorophenylacetyl chloride 
• 181026-78-8 1,1-bis(trimethylsilyloxy)-2-chloro-2-phenylethene 
• 2835-06-5 phenylglycin 

Downstream Products

• 611-71-2 MANDELIC ACID 
• 53432-40-9 (R)-chloro-phenyl-acetic acid-chloride 
• 103-82-2 phenylacetic acid 
• 117-34-0 2,2-diphenylacetic acid 
• 7584-72-7 meso-2,3-diphenylsuccinic acid 
• 2611-88-3 (S)-(+)-α-methylamino phenylacetic acid 
• 646058-06-2 (S)-2-dodecylthiophenylacetic acid 
• 59204-21-6 Methyl (R)-2-chloro-2-phenylethanoate 
• 65117-30-8 (R)-chloro-phenyl-acetic acid dimethylamide 
• 588-64-7 benzaldehyde phenylhydrazone 

Relevant articles and documents

Catalytic asymmetric α-chlorination of 3-acyloxazolidin-2-one with a trinary catalytic system

Direct asymmetric α-chlorination of aryl acetic acid derivatives was achieved with a novel trinary activation system consisting of a catalytic amount of NiCl2/(R)-BINAP, Et3SiOTf, and a tertiary amine base. The reaction smoothly affo

Nitrile hydratase activity of a recombinant nitrilase

Appreciable amounts of amide are formed in the course of nitrile hydrolysis in the presence of recombinant nitrilase from Pseudomonas fluorescens EBC 191, depending on the α-substituent and the reaction conditions. The ratio of the nitrilase and nitrile hydratase activities of the enzyme is profoundly influenced by the electronic and steric properties of the reactant. In general, amide formation increased when the α-substituent was electron-deficient; 2-chloro-2-phenylacetonitrile, for example, afforded 89% amide. We found, moreover, that (R)-mandelo-nitrile was hydrolysed with 11% of amide formation whereas 55% amide was formed from the (S)-enantiomer; a similar effect was found for the O-acetyl derivatives. A mechanism that accomodates our results is proposed.

PROCESSES FOR THE PRODUCTION OF OPTICALLY ACTIVE COMPOUNDS HAVING SUBSTITUENTS AT THE 2-POSITION

The present invention provides a process for producing an optically active compound having a thio group at the 2-position important for manufacturing medicines. An optically active compound having a hydroxyl group at the 2-position is chlorinated with inv

Enzymatic hydrolysis and selective racemisation reactions of α-chloro esters

The kinetic resolution of α-chloro esters was effected with good selectivity using CLEC (Cross-Linked Enzyme Crystals) enzymes. The selective racemisation of α-chloro esters in the presence of α-chloro acids enabled a successful dynamic kinetic resolution reaction to be performed.

Enantioselective protonation of silyl enol ethers and ketene disilyl acetals with Lewis acid-assisted chiral Bronsted acids: Reaction scope and mechanistic insights

Enantioselective protonation is a potent and efficient way to construct chiral carbons. Here we report details of the reaction using Lewis acid-assisted chiral Bronsted acids (chiral LBAs). The 1:1 coordinate complex of tin tetrachloride and optically active binaphthol ((R)- or (S)-BINOL) can directly protonate various silyl enol ethers and ketene disilyl acetals to give the corresponding α-aryl ketones and α-arylcarboxylic acids, respectively, with high enantiomeric excesses (up to 98% ee). A catalytic version of enantioselective protonation has also been achieved using stoichiometric amounts of 2,6-dimethylphenol and catalytic amounts of monomethyl ether of optically active BINOL in the presence of tin tetrachloride. This protonation is also effective for producing α-halocarbonyl compounds (up to 91% ee). DFT calculations on the B3LYP/LANL2DZ level show that the conformational structure of the chiral LBA and the orientation of activated proton on (R)-BINOLs are important for understanding the absolute stereochemistry of the products.

Effect of fluorine substitution of α-and β-hydrogen atoms in ethyl phenylacetate and phenylpropionate on their stereoselective hydrolysis by cultured cancer cells

(±)-Ethyl 2-fluoro-2-phenylacetate was stereoselectively hydrolyzed by cultured cells of several rat cancer cell lines to give the carboxylic acid rich in the R enantiomer. The stereoselectivity increased for (±)-ethyl 2-fluoro-2-phenylpropionate (2b) with all present cell lines and for (±)-ethyl 2-phenyl-3,3,3-trifluoropropionate (3b) with rat hepatoma McA-RH7777 cell line. The stereoselectivity was different for the different cell lines, as McA-RH7777 cells preferred (R)-2b in contrast with the preference towards (S)-2b by other cells such as ras oncogene-transformed rat liver Anr4 cells. These stereoselectivities were different from those for non-fluorinated (±)-ethyl 2-phenylpropionate. Thus fluorine atoms are recognized by ester hydrolases of cancer cells, and fluorine substitution on the acyl group will be useful for making ester-type anticancer prodrugs more specific to cancer cells.

Enantioselective Protonation of Ketene Bis(trimethylsilyl) Acetals Derived from α-Aryl-α-haloacetic Acids Using LBA

Optically active α-halocarboxylic acids and derivatives are important and versatile building blocks in organic synthesis. Lewis acid assisted chiral Bronsted acid (LBA) was recently prepared in situ from tin(IV) tetrachloride and optically pure binaphthol