29125-24-4

Basic information

• Product Name: S-2-Chloro-2-phenylacetic acid
• Synonyms: (S)-Phenylchloroacetic acid;[S,(+)]-Chlorophenylacetic acid
• CAS NO: 29125-24-4
• Molecular Formula: C₈H₇ClO₂
• Molecular Weight: 170.59
• Mol File: 29125-24-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 60-61 °C(Solv: ethanol (64-17-5))
• Boiling Point: 125-126 °C(Press: 3 Torr)
• Appearance: /
• Density: 0.8837 g/cm3
• PKA: 2.40±0.10(Predicted)
• CAS DataBase Reference: S-2-Chloro-2-phenylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: S-2-Chloro-2-phenylacetic acid(29125-24-4)
• EPA Substance Registry System: S-2-Chloro-2-phenylacetic acid(29125-24-4)

Safety Data

• Hazardous Substances Data: 29125-24-4(Hazardous Substances Data)

Usage

General Description

S-2-Chloro-2-phenylacetic acid is a chemical compound with the molecular formula C8H7ClO2. It is a chiral compound with two enantiomers, a (S)-enantiomer and a (R)-enantiomer. S-2-Chloro-2-phenylacetic acid is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It is also known for its application in the production of chiral auxiliaries, which are used as building blocks for the synthesis of various organic compounds. S-2-Chloro-2-phenylacetic acid is a versatile compound with potential uses in the pharmaceutical and agrochemical industries.

Upstream product

• 611-71-2 (R)-Mandelic Acid 
• 1355255-19-4 (+/-)-3-(2-chloro-2-phenylacetyl)oxazolidin-2-one 
• 17199-29-0 (S)-Mandelic acid 
• 22259-83-2 2-chloro-2-phenylacetonitrile 
• 10606-73-2 ethyl 2-chloro-2-phenylacetate 
• 22060-02-2 β-Chlor-ethylphenylchloracetat 
• 7476-66-6 methyl 2-chloro-2-phenylethanoate 
• 464-45-9 endo-borneol 
• 2216-51-5 (-)-menthol 
• 181026-78-8 1,1-bis(trimethylsilyloxy)-2-chloro-2-phenylethene 
• 4755-72-0 Chloro-phenyl-acetic acid 
• 2912-62-1 α-chlorophenylacetyl chloride 

Downstream Products

• 10606-72-1 (R)-mandelic acid ethyl ester 
• 10606-73-2 (S)-2-chloro-2-phenylacetic acid ethyl ester 
• 62600-43-5 C₈H₆Cl₂O 
• 2835-06-5 phenylglycin 

Relevant articles and documents

Aromatic cation activation: Nucleophilic substitution of alcohols and carboxylic acids

A new method for the nucleophilic substitution of alcohols and carboxylic acids using aromatic tropylium cation activation has been developed. This article reports the use of chloro tropylium chloride for the rapid generation of alkyl halides and acyl chlorides under very mild reaction conditions. It demonstrates, for the first time, the synthetic potential of tropylium cations in promoting chemical transformations.

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.

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.