52923-23-6

Basic information

• Product Name: (2R)-HYDROXY(3-CHLOROPHENYL)ACETICACID
• Synonyms: (2R)-HYDROXY(3-CHLOROPHENYL)ACETICACID
• CAS NO: 52923-23-6
• Molecular Formula: C₈H₇ClO₃
• Molecular Weight: 0
• Mol File: 52923-23-6.mol
• Article Data: 54

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2R)-HYDROXY(3-CHLOROPHENYL)ACETICACID(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-HYDROXY(3-CHLOROPHENYL)ACETICACID(52923-23-6)
• EPA Substance Registry System: (2R)-HYDROXY(3-CHLOROPHENYL)ACETICACID(52923-23-6)

Safety Data

• Hazardous Substances Data: 52923-23-6(Hazardous Substances Data)

Usage

General Description

(2R)-HYDROXY(3-CHLOROPHENYL)ACETIC ACID, also known as 3-(2-hydroxyphenyl)-2-propenoic acid, is a chemical compound with the molecular formula C8H8O3Cl. It is a derivative of phenylacetic acid and contains a hydroxyl group and a chlorine atom on the phenyl ring. (2R)-HYDROXY(3-CHLOROPHENYL)ACETICACID has potential pharmaceutical applications and is being studied for its anti-inflammatory, analgesic, and antipyretic properties. Its stereochemistry, with the (2R) configuration, is important for its biological activity and interactions with other molecules within the body. The compound is also used as a chiral resolving agent in the synthesis of pharmaceutical intermediates. It is important to handle this compound with care, as it may have hazardous effects if not used properly.

Upstream product

• 75-25-2 Bromoform 
• 89-98-5 2-chloro-benzaldehyde 
• 10421-85-9 2-chloromandelic acid 
• 178437-75-7 2-acetoxy-2-(2-chlorophenyl)acetic acid 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 74-90-8 hydrogen cyanide 
• 118-91-2 ortho-chlorobenzoic acid 
• 13011-88-6 2-(2-chloro-phenyl)-5-imino-2,5-dihydro-furan-3,4-diol 
• 67-66-3 chloroform 
• 13312-84-0 2-chloromandelonitrile 
• 102767-28-2 levetiracetam 
• 62-76-0 sodium oxalate 
• 694-80-4 2-bromo-1-chlorobenzene 
• 34966-49-9 methyl 2-chlorobenzoylformate 

Downstream Products

• 156276-21-0 rac-methyl 2-chloromandelate 
• 13511-30-3 ethyl 2-(2-chlorophenyl)-2-hydroxyacetate 
• 29270-30-2 α-bromo-2-chlorophenyl acetic acid 
• 80173-43-9 chloro-(2-chloro-phenyl)-acetic acid ethyl ester 
• 34113-46-7 1-(2-chlorophenyl)-1-(4-chlorophenyl)acetic acid 
• 35599-96-3 2-(2-chlorophenyl)-2-methoxyacetic acid 
• 62123-75-5 ethyl 2-(2-chlorophenyl)-2-oxoacetate 
• 10421-85-9 (R)-2-chloromandelic acid 
• 132274-47-6 N-(2-phenylethyl)-2-chloromandelamide 
• 132274-48-7 N-(2-(4-chlorophenyl)ethyl)-2-chloromandelamide 
• 10421-85-9 (S)-2-chloromandelic acid 
• 32345-60-1 methyl (S)-2-hydroxy-2-(2-chlorophenyl)acetate 
• 1353949-47-9 2-(2-chlorophenyl)-(R)-2-hydroxy-N-methoxy-N-methylacetamide 
• 1353949-55-9 1-(2-chlorophenyI)-(R)-1-(methoxymethoxy)-(S)-2-propanol 

Relevant articles and documents

Resolution of halogenated mandelic acids through enantiospecific co-crystallization with levetiracetam

The resolution of halogenated mandelic acids using levetiracetam (LEV) as a resolving agent via forming enantiospecific co-crystal was presented. Five halogenated mandelic acids, 2-chloromandelic acid (2-ClMA), 3-chloromandelic acid (3-ClMA), 4-chloromandelic acid (4-ClMA), 4-bromomandelic acid (4-BrMA), and 4-fluoromandelic acid (4-FMA), were selected as racemic compounds. The effects of the equilibrium time, molar ratio of the resolving agent to racemate, amount of solvent, and crystallization temperature on resolution performance were investigated. Under the optimal conditions, the resolution efficiency reached up to 94% and the enantiomeric excess (%e.e.) of (R)-3-chloromandelic acid was 63%e.e. All five halogenated mandelic acids of interest in this study can be successfully separated by LEV via forming enantiospecific co-crystal, but the resolution performance is significantly different. The results showed that LEV selectively co-crystallized with S enantiomers of 2-ClMA, 3-ClMA, 4-ClMA, and 4-BrMA, while it co-crystallized with R enantiomers of 4-FMA. This indicates that the position and type of substituents of racemic compounds not only affect the co-crystal configuration, but also greatly affect the efficiency of co-crystal resolution.

Oxalyl-CoA Decarboxylase Enables Nucleophilic One-Carbon Extension of Aldehydes to Chiral α-Hydroxy Acids

The synthesis of complex molecules from simple, renewable carbon units is the goal of a sustainable economy. Here we explored the biocatalytic potential of the thiamine-diphosphate-dependent (ThDP) oxalyl-CoA decarboxylase (OXC)/2-hydroxyacyl-CoA lyase (HACL) superfamily that naturally catalyzes the shortening of acyl-CoA thioester substrates through the release of the C1-unit formyl-CoA. We show that the OXC/HACL superfamily contains promiscuous members that can be reversed to perform nucleophilic C1-extensions of various aldehydes to yield the corresponding 2-hydroxyacyl-CoA thioesters. We improved the catalytic properties of Methylorubrum extorquens OXC by rational enzyme engineering and combined it with two newly described enzymes—a specific oxalyl-CoA synthetase and a 2-hydroxyacyl-CoA thioesterase. This enzymatic cascade enabled continuous conversion of oxalate and aromatic aldehydes into valuable (S)-α-hydroxy acids with enantiomeric excess up to 99 %.

Method for preparing alpha-hydroxy acid

The invention relates to the technical field of organic chemical asymmetric hydrogenation, specifically to a method for catalyzing an asymmetric hydrogenation alpha-ketonic acid compound to prepare achiral alpha-hydroxy acid compound. The method is simple in synthesis route, high in conversion rate and high in ee value.