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10421-85-9

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10421-85-9 Usage

Chemical Properties

White to pale cream crystalline powder

Uses

2-Chloromandelic acid, is used as a pharmaceutical intermediate as well as in the medicine industry. It is used as a intermediate of clopidrogrel.

General Description

2-Chloromandelic acid (2-ClMA) is a mandelic acid derivative. A report based on its solid state-NMR, X-ray powder diffraction (XPRD) and Fourier transform infrared spectroscopy (FTIR) data reveals that in solid state 2-ClMA exists as a racemic compound. The study also suggests that the crystals of racemic 2-ClMA belongs the monoclinic space group P21/c. The efficiency of (R)-(+)-N-benzyl-1-phenylethylamine in resolving racemate 2-ClMA has been investigated.

Check Digit Verification of cas no

The CAS Registry Mumber 10421-85-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,4,2 and 1 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 10421-85:
(7*1)+(6*0)+(5*4)+(4*2)+(3*1)+(2*8)+(1*5)=59
59 % 10 = 9
So 10421-85-9 is a valid CAS Registry Number.
InChI:InChI=1/C8H7ClO3/c9-6-4-2-1-3-5(6)7(10)8(11)12/h1-4,7,10H,(H,11,12)/p-1/t7-/m1/s1

10421-85-9 Well-known Company Product Price

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  • Alfa Aesar

  • (B21525)  2-Chloromandelic acid, 98%   

  • 10421-85-9

  • 5g

  • 291.0CNY

  • Detail
  • Alfa Aesar

  • (B21525)  2-Chloromandelic acid, 98%   

  • 10421-85-9

  • 25g

  • 1021.0CNY

  • Detail
  • Alfa Aesar

  • (B21525)  2-Chloromandelic acid, 98%   

  • 10421-85-9

  • 100g

  • 3460.0CNY

  • Detail

10421-85-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Chloromandelic Acid

1.2 Other means of identification

Product number -
Other names 2-(2-chlorophenyl)-2-hydroxyacetic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:10421-85-9 SDS

10421-85-9Relevant articles and documents

-

Compere Jr.

, p. 2565 (1968)

-

One-pot, single-step deracemization of 2-hydroxyacids by tandem biocatalytic oxidation and reduction

Xue, Ya-Ping,Zheng, Yu-Guo,Zhang, Ya-Qin,Sun, Jing-Lei,Liu, Zhi-Qiang,Shen, Yin-Chu

, p. 10706 - 10708 (2013)

A facile and efficient one-pot, single-step method for deracemizing a broad range of 2-hydroxyacids to (R)-2-hydroxyacids was established by combination of resting cells of an (S)-hydroxyacid dehydrogenase-producing microorganism and an (R)-ketoacid reductase-producing microorganism.

The phase behavior and crystallization of 2-chloromandelic acid: The crystal structure of the pure enantiomer and the behavior of its metastable conglomerate

Lorenz, Heike,Von Langermann, Jan,Sadiq, Ghazla,Seaon, Colin C.,Davey, Roger J.,Seidel-Morgenstern, Andreas

, p. 1549 - 1556 (2011)

Crystallization of racemic 2-chloromandelic acid yields a metastable conglomerate in addition to a more stable racemic compound. The crystal structure of the pure enantiomer is reported and the relative stability of the racemic compound and conglomerate was determined at both room temperature and the melting point. Crystallizations from melt and solution are shown to offer potential crystallization pathways to the conglomerate, provided crystallization of the racemic compound can be avoided.

β-Cyclodextrin-teba: A new catalyst system for selective synthesis of α-hydroxyacids

Zhou,Yuan,Xie

, p. 43 - 46 (1994)

The presence of β-cyclodextrin (β-CD) and triethylbenzyl ammonium chloride (TEBA) favors the one-pot reaction of aromatic aldehydes, chloroform and sodium hydroxide to give α- hydroxyarylacetic acids in 81% ~ 89% yields.

Biocatalytic racemization of aliphatic, arylaliphatic, and aromatic α-hydroxycarboxylic acids

Glueck, Silvia M.,Pirker, Monika,Nestl, Bettina M.,Ueberbacher, Barbara T.,Larissegger-Schnell, Barbara,Csar, Katrin,Hauer, Bernhard,Stuermer, Rainer,Kroutil, Wolfgang,Faber, Kurt

, p. 4028 - 4032 (2005)

Biocatalytic racemization of a range of aliphatic, (aryl)aliphatic, and aromatic α-hydroxycarboxylic acids was accomplished by using whole resting cells of a range of Lactobacillus spp. The mild (physiological) reaction conditions ensured an essentially "clean" isomerization in the absence of side reactions, such as elimination or decomposition. Whereas straight-chain aliphatic 2-hydroxy-carboxylic acids were racemized with excellent rates (up to 85% relative to lactate), steric hindrance was observed for branched-chain analogues. Good rates were observed for aryl-alkyl derivatives, such as 3-phenyllactic acid (up to 59%) and 4-phenyl-2-hydroxybutanoic acid (up to 47%). In addition, also mandelate and its o-chloro analogue were accepted at a fair rate (45%). This biocatalytic racemization represents an important tool for the deracemization of a number of pharmaceutically important building blocks.

Improved apparent enantioselectivity of a hydrolase by sequential hydrolysis and racemization

Gu, Jiali,Ye, Lidan,Guo, Fei,Lv, Xiaomei,Lu, Wenqiang,Yu, Hongwei

, p. 1489 - 1491 (2015)

Further improvement of the enantioselectivity of hydrolases with moderate enantioselectivity is of important significance to fulfill the requirement in industrial application. Herein, a strategy based on sequential hydrolysis and racemization was adopted, using esterase BioH from Escherichia coli as an example. After coupling with a mandelate racemase, the E value of esterase BioH toward methyl (S)-o-chloromandelate was enhanced from 73 to 162, demonstrating the effectiveness of this strategy.

Semirational Design of Fluoroacetate Dehalogenase RPA1163 for Kinetic Resolution of α-Fluorocarboxylic Acids on a Gram Scale

Chen, Bo,Li, Min,Li, Yanwei,Ma, Ming,Tian, Shaixiao,Tong, Wei,Wang, Jian-Bo,Xu, Guangyu,Yue, Yue,Zhang, Hongxia

, p. 3143 - 3151 (2020)

Here the synthetic utility of fluoroacetate dehalogenase RPA1163 is explored for the production of enantiomerically pure (R)-α-fluorocarboxylic acids and (R)-α-hydroxylcarboxylic acids via kinetic resolution of racemic α-fluorocarboxylic acids. While wild-type (WT) RPA1163 shows high thermostability and fairly wide substrate scope, many interesting yet poorly or moderately accepted substrates exist. In order to solve this problem and to develop upscaled production, in silico calculations and semirational mutagenesis were employed. Residue W185 was engineered to alanine, serine, threonine, or asparagine. The two best mutants, W185N and W185T, showed significantly improved performance in the reactions of these substrates, while in silico calculations shed light on the origin of these improvements. Finally, 10 α-fluorocarboxylic acids and 10 α-hydroxycarboxylic acids were prepared on a gram scale via kinetic resolution enabled by WT, W185T, or W185N. This work expands the biocatalytic toolbox and allows a deep insight into the fluoroacetate dehalogenase catalyzed C-F cleavage mechanism.

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

Peng, Yangfeng,Wang, Jie

, (2021/09/18)

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

Burgener, Simon,Cortina, Ni?a Socorro,Erb, Tobias J.

supporting information, p. 5526 - 5530 (2020/02/20)

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 %.

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