25333-13-5

Basic information

• Product Name: Propanoic acid,2-(4-chloro-2-methylphenoxy)-, (2S)-
• Synonyms: Propanoicacid, 2-(4-chloro-2-methylphenoxy)-, (S)-; Propionic acid,2-[(4-chloro-o-tolyl)oxy]-, (-)- (8CI);(-)-2-(4-Chloro-2-methylphenoxy)propanoic acid;(-)-2-(4-Chloro-2-methylphenoxy)propionic acid; (-)-Mecoprop; (S)-(-)-Mecoprop;(S)-Mecoprop
• CAS NO: 25333-13-5
• Molecular Formula: C10H11 Cl O3
• Molecular Weight: 214.649
• Mol File: 25333-13-5.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Propanoic acid,2-(4-chloro-2-methylphenoxy)-, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Propanoic acid,2-(4-chloro-2-methylphenoxy)-, (2S)-(25333-13-5)
• EPA Substance Registry System: Propanoic acid,2-(4-chloro-2-methylphenoxy)-, (2S)-(25333-13-5)

Safety Data

• Hazardous Substances Data: 25333-13-5(Hazardous Substances Data)

Upstream product

• 93-65-2 (RS)-2-(4-chloro-o-tolyloxy)propionic acid 
• 94559-03-2 2-(4-Chloro-2-methyl-phenoxy)-propionic acid (R)-1-pyridin-4-yl-ethyl ester 
• 52106-86-2 sodium 4-chloro-2-methyl-phenolate 
• 62784-66-1 bis(1-naphthyl)methanol 
• 1570-64-5 2-methyl-4-chlorophenol 
• 40390-11-2 (S)-Ethyl 2-(4-chloro-2-methylphenoxy)propanoate 
• 27854-88-2 (R)-1-(4-pyridinyl)ethanol 
• 42383-63-1 2-(4-Chlor-2-methylphenoxy)propionsaeureanhydrid 
• 23844-56-6 methyl R-2-(4-chloro-2-methylphenoxy)propanoate 

Downstream Products

• 92446-90-7 (S)-(+)-2-methyl-2-(4-chloro-2-methylphenoxy)ethanol 

Relevant articles and documents

HPLC separation of 2-aryloxycarboxylic acid enantiomers on chiral stationary phases

The possibility for separating enantiomers of a number of practically significant 2-aryloxycarboxylic acids was studied by normal- and reversed-phase HPLC on popular chiral stationary phases. The best separation parameters were achieved on the chiral phases with the polysaccharide base Chiralcel OD-H and Chiralpack AD under the normal-phase HPLC conditions. The (S)- and (R)-enantiomers of 2-(1-naphthyloxy)- and 2-(2-iodophenoxy)propionic acids with enantiomeric excess ee >99% were isolated using preparative chiral HPLC.

A new method for production of chiral 2-aryloxypropanoic acids using effective kinetic resolution of racemic 2-aryloxycarboxylic acids

We report a novel method for the preparation of 2-aryloxypropanoic acids by kinetic resolution of racemic 2-aryloxypropanoic acids using enantioselective esterification. The usage of pivalic anhydride (Piv2O) as an activating agent, bis(a-naphthyl)methanol ((α-Np)2CHOH) as an achiral alcohol, and (+)-benzotetramisole ((+)-BTM) as a chiral acyl-transfer catalyst enables the effective separation of various racemic 2-aryloxypropanoic acids to afford optically active carboxylic acids and the corresponding esters with high enantioselectivities. Furthermore, theoretical calculations of the transition states required to form the chiral esters successfully proved the enantiomer recognition mechanism of the asymmetric esterification.

Carboxylic acids and skeletal muscle chloride channel conductance: Effects on the biological activity induced by the introduction of methyl groups on the aromatic ring of chiral α-(4-chloro-phenoxy)alkanoic acids

One or two methyl groups have been introduced on the aromatic ring of two chiral clofibric acid analogs, 2-(4-chloro-phenoxy)propanoic and 2-(4-chloro-phenoxy)butanoic acids. The biological activity of the derivatives obtained (3-6) has been evaluated on the skeletal muscle chloride conductance (gCl). The results confirm the hypothesis of two different sites modulating chloride channel function, an excitatory site that increases channel activity and an inhibitory site that produces a channel block. In fact, this chemical modification strongly reduces the blocking activity of the (R)-and (S)-enantiomers in comparison with the parent compounds, but does not markedly affect the ability of the (R)-enantiomers to increase chloride channel conductance.