86169-24-6

Basic information

• Product Name: D-(+)-(2-Chlorophenyl)glycine
• Synonyms: D-(-)-(2-CHLOROPHENYL)GLYCINE;D-(+)-(2-CHLOROPHENYL)GLYCINE;D-(2-CHLOROPHENYL)GLYCINE;2-CHLORO-D-PHENYLGLYCINE;(R)-AMINO-(2-CHLORO-PHENYL)-ACETIC ACID;R-(-)-2-Chlorophenylglycine;(S)-2-Amino-2-(2-chlorophenyl)acetic acid;(R)-(-)-2-Chlorophenylglycine, D-2-Amino-2-(2-chlorophenyl)ethanoic acid
• CAS NO: 86169-24-6
• Molecular Formula: C₈H₈ClNO₂
• Molecular Weight: 185.61
• EINECS: 1533716-785-6
• Product Categories: Pharmaceutical Intermediates;Amino ACIDS SERIES
• Mol File: 86169-24-6.mol

Chemical Properties

• Melting Point: 182-187 °C(lit.)
• Boiling Point: 318.8 °C at 760 mmHg
• Flash Point: 146.6 °C
• Appearance: /
• Density: 1.392 g/cm³
• Storage Temp.: 2-8°C
• PKA: 1.69±0.10(Predicted)
• CAS DataBase Reference: D-(+)-(2-Chlorophenyl)glycine(CAS DataBase Reference)
• NIST Chemistry Reference: D-(+)-(2-Chlorophenyl)glycine(86169-24-6)
• EPA Substance Registry System: D-(+)-(2-Chlorophenyl)glycine(86169-24-6)

Safety Data

• Hazardous Substances Data: 86169-24-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
D-(+)-(2-Chlorophenyl)glycine is used as an intermediate in the production of various drugs, including antipsychotics and anti-cancer medications. Its unique chiral structure allows for the development of enantiomerically pure compounds, which are essential for achieving desired therapeutic effects and minimizing side effects.
Used in Agrochemical Industry:
D-(+)-(2-Chlorophenyl)glycine is used as a precursor in the manufacture of agricultural chemicals. Its incorporation into these products helps improve their efficacy and selectivity, leading to more effective pest control and crop protection.
Used in Fine Chemicals Industry:
D-(+)-(2-Chlorophenyl)glycine is also utilized in the synthesis of other fine chemicals, further expanding its applications across various industries. Its versatility as a building block enables the creation of a wide range of specialized compounds for different purposes.

Upstream product

• 103029-09-0 5-(2-chlorophenyl)imidazolidine-2,4-dione 
• 143-33-9 sodium cyanide 
• 89-98-5 2-chloro-benzaldehyde 
• 13312-84-0 2-chloromandelonitrile 
• 1253091-76-7 methyl 2-((tert-butoxycarbonyl)amino)-2-(2-chlorophenyl)acetate 
• 2039-87-4 2-chlorostyrene 
• 10421-85-9 2-chloromandelic acid 
• 187243-26-1 N-(o-chlorophenyl)hydantoin 
• 144616-14-8 ortho-chlorophenylmalonic acid 

Downstream Products

• 111-85-3 n-chlorooctane 
• 131402-95-4 Amino-(2-chloro-phenyl)-acetic acid octyl ester; hydrochloride 
• 808732-87-8 α-(2-thiophenylethylamino)-o-chlorophenylacetic acid 
• 141315-51-7 S(+)-chlorophenylglycine-d-camphoric sulfonic acid 
• 141109-14-0 2-(2-chlorophenyl)glycine methyl ester hydrochloride 
• 29270-30-2 α-bromo-2-chlorophenyl acetic acid 
• 313490-25-4 [(tert-butoxycarbonyl)amino](2-chlorophenyl)acetic acid 
• 127428-62-0 2-amino-2-(2-chlorophenyl)ethan-1-ol 
• 1276118-73-0 C₁₁H₁₃ClN₂O 
• 1276118-74-1 C₁₂H₁₅ClN₂O 
• 1276118-75-2 C₁₃H₁₇ClN₂O 
• 1276118-81-0 C₁₆H₁₄ClNO₂ 
• 1313411-65-2 C₁₉H₁₇ClN₂O₂ 
• 1276118-82-1 C₁₂H₁₃ClN₂O₂ 

Relevant articles and documents

Method for continuously and quickly preparing DL-phenylglycine and analogue thereof

The invention provides a method for continuously and quickly preparing DL-phenylglycine and an analogue thereof. The method comprises the steps of adding 2-hydroxyl-phenylacetonitrile and an analoguethereof (cyanohydrin for short) and an aqueous ammonium bicarbonate solution into a microchannel reactor for a reaction, controlling the reaction temperature to be 80-130 DEG C, and controlling the reaction pressure to be 0.5-2.0 MPa, wherein the standing time of the reactants in a microchannel is 1-8 min, and an aqueous solution of 5-phenyl-hydantoin and an analogue thereof (hydantoin for short)is obtained; adding the hydantoin and alkali into the microchannel reactor for a reaction, controlling the reaction temperature to be 120-200 DEG C, and controlling the reaction pressure to be 1.0-3.5MPa, wherein the standing time of the reactants in the microchannel is 1-8 min, and then a saline solution of phenylglycine and an analogue thereof is obtained; conducting acidification neutralization and crystallization to obtain the phenylglycine and the analogue thereof. According to the method, the microchannel reactor is adopted, the reaction time is greatly shorted, the reaction speed is increased, pyrolysis and polymerization of the cyanohydrin are reduced, no by-products are generated, the products are high in yield, clean and environmentally friendly, and the production cost is lowered.

One-Pot Enantioselective Synthesis of d-Phenylglycines from Racemic Mandelic Acids, Styrenes, or Biobased l-Phenylalanine via Cascade Biocatalysis

Enantiopure d-phenylglycine and its derivatives are an important group of chiral amino acids with broad applications in thepharmaceutical industry. However, the existing synthetic methods for d-phenylglycine mainly rely on toxic cyanide chemistry and multistep processes. To provide green and safe alternatives, we envisaged cascade biocatalysis for the one-pot synthesis of d-phenylglycine from racemic mandelic acid, styrene, and biobased l-phenylalanine, respectively. Recombinant Escherichia coli (LZ110) was engineered to coexpress four enzymes to catalyze a 3-step reaction in one pot, transforming mandelic acid (210 mM) to give enantiopure d-phenylglycine in 29.5 g L?1 (195 mM) with 93% conversion. Using the same whole-cell catalyst, twelve other d-phenylglycine derivatives were also produced from the corresponding mandelic acid derivatives in high conversion (58–94%) and very high ee (93–99%). E. coli (LZ116) expressing seven enzymes was constructed for the transformation of styrene to enantiopure d-phenylglycine in 80% conversion via a one-pot 6-step cascade biotransformation. Twelve substituted d-phenylglycines were also produced from the corresponding styrene derivatives in high conversion (45–90%) and very high ee (92–99%) via the same cascade reactions. A nine-enzymeexpressing E. coli (LZ143) was engineered to transform biobased l-phenylalanine to enantiopure d-phenylglycine in 83% conversion via a one-pot 8-step transformation. Preparative biotransformations were also demonstrated. The high-yielding synthetic methods use cheap and green reagents (ammonia, glucose, and/or oxygen), and E. coli whole-cell catalysts, thus providing green and useful alternative methods for manufacturing d-phenylglycine. (Figure presented.).

Preparation method for D, L-phenylglycine and analogue thereof

The invention provides a preparation method for D, L-phenylglycine and an analogue thereof. According to the method, benzaldehyde, an analogue thereof and hydrocyanic acid are adopted as raw materials and subjected to cyanidation reaction, and then 2-hydroxy-benzyl cyanide or 2-hydroxy-benzyl cyanide analogue (cyanohydrin for short) is generated. Cyanohydrin reacts with carbon dioxide and the aqueous solution of ammonia, and then 5-phenyl-hydantoin and an analogue thereof (hydantoin for short) are generated. hydantoin is successively subjected to steam stripping, alkaline hydrolysis, steam stripping, decolorization, neutralization, crystallization, washing, centrifuging, drying and the like to obtain D, L-phenylglycine and the analogue thereof. Compared with the prior art, the preparation method for D, L-phenylglycine and the analogue thereof can significantly and effectively reduce the pollution, and fewer inorganic salt by-products are generated. Meanwhile, the prepared D, L-phenylglycine and the analogue thereof are high in product yield and high in purity. Counted in benzaldehyde and the analogue thereof, the yield of D, L-phenylglycine and the analogue thereof is larger than or equal to 96%, and the product purity is larger than or equal to 99%. Meanwhile, the process flow is simple and feasible, so that the method is worthy of market popularization and application.

High yield synthesis of d-phenylglycine and its derivatives by nitrilase mediated dynamic kinetic resolution in aqueous-1-octanol biphasic system

A strategy of nitrilase mediated dynamic kinetic resolution toward the synthesis of d-phenylglycine was developed, using aqueous-1-octanol biphasic system. Due to the efficient suppression of the decomposition of phenylglycinonitrile, a maximum yield of 81% is obtained. This result indicates that the nitrilase mediated dynamic kinetic resolution is a promising method toward the synthesis of d-phenylglycine and its derivatives.

Chemo-enzymatic approach to the synthesis of the antithrombotic clopidogrel

The (S)-2-chlorophenylglycine moiety is well recognized in the structure of (S)-clopidogrel, a known antithrombotic drug. We prepared an enantiomerically pure chiral building block via an enzyme-catalyzed resolution of (RS)-N-Boc-2-chlorophenylglycine methylester. The best results were obtained by means of an immobilized subtilisin, the cross-linked enzyme aggregate (Alcalase-CLEA). The high enantiomeric excess of the synthon obtained remained the same over the course of clopidogrel synthesis; the simplicity of the process makes this pathway suitable for large-scale preparation.

Process for preparation of 2-chlorophenylglycine derivatives and enantiomerically separation

The present invention relates to novel processes and intermediates for the preparation of R(?)-α-2-chlorophenylglycine, S(+)-α-2-chlorophenylglycine, and RS-2-chlorophenylglycine derivatives of formulas I, II and III, respectively. The resulting enantioseparative system was validated in order to evaluate the presence of the enantiomer in pharmaceutical samples. These compounds are found useful as an active ingredient for the pharmaceutical intermediate or as an active ingredient as the tools for delivery of drugs.

Production of ring-substituted D-phenylglycines by microbial or enzymatic hydrolysis/deracemisation of the corresponding DL-hydantoins

A series of 17 ring-mono and -disubstituted D-phenylglycine derivatives was prepared in high enantiomeric purity by enzymatic hydrolysis and deracemisation of the corresponding DL-hydantoins, using D-hydantoinase activities of microorganisms or purified enzymes, followed by diazotation of the resulting N-carbamyl-D-amino acids. No significant L-hydantoinase activity was found to produce the corresponding L-enantiomers.