2-(2-Chlorophenyl)glycine Chemical Properties

Melting point:

218-220 °C (decomp)

Boiling point:

318.8±32.0 °C(Predicted)

Density 

1.392±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

form 

Powder

pka

1.69±0.10(Predicted)

color 

White to off-white

Sensitive 

Air Sensitive

CAS DataBase Reference

88744-36-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

F 

10-23

HS Code 

29224985

MSDS

• Language:English Provider:SigmaAldrich

2-(2-Chlorophenyl)glycine Usage And Synthesis

Description

2-(2-Chlorophenyl)glycine is a pharmaceutical intermediate ingredient used in the preparation of Clopidogrel hydrogensulfate, an antiplatelet drug used to prevent blood clots.

Uses

2-Chlorophenylglycine is a Glycine.html" class="link-product" target="_blank">Glycine (HY-Y0966) derivative[1].

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

The general procedure for the synthesis of (R)-2-amino-2-(2-chlorophenyl)acetic acid from sodium cyanide and o-chlorobenzaldehyde was as follows: 2-chlorophenylglycine was prepared according to the method described in Scheme 1. O-chlorobenzaldehyde (2-chlorobenzaldehyde), ammonium bicarbonate (NH4HCO3, 23.7 g) and sodium cyanide (NaCN, 14.7 g) were dissolved in a mixed solvent of 500 ml of methanol and 500 ml of water, and the reaction was stirred for 5 hours at 65-70 °C. Upon completion of the reaction, the solution was concentrated and transferred to an autoclave, where 45% sodium hydroxide (NaOH) solution was added and refluxed at 120°C for 4 hours. After the reaction mixture was cooled, 2 g of activated carbon was added and stirred for 10 minutes for decolorization. The activated carbon was removed by filtration and the pH of the filtrate was adjusted to 7-8 with 50% sulfuric acid (H2SO4). the precipitate was collected by filtration and washed with water to give 27 g (58% yield) of 2-chlorophenylglycine. The product was RS-2-chlorophenylglycine with a specific optical rotation of +0.16 (C=1, 1N HCl) and a melting point of 185.4-186.8 °C. The product was a mixture of RS-2-chlorophenylglycine, RS-2-chlorophenylglycine and RS-2-chlorophenylglycine.

References

[1] Luckose F, et al. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1144. DOI:10.1080/10408398.2012.708368

2-(2-Chlorophenyl)glycine(88744-36-9)Related Product Information

• AMINO-(2-CHLORO-PHENYL)-ACETIC ACID,DL-2-Chlorophenylglycine/D-Amino-(2-chloro-phenyl)-acetic acid
• 2-Chlorophenylacetic acid
• AMINO-(3-CHLORO-PHENYL)-ACETIC ACID,(S)-AMINO-(3-CHLORO-PHENYL)-ACETIC ACID
• (R)-AMINO-(2-CHLORO-PHENYL)-ACETIC ACID
• (S)-AMINO-(2-CHLORO-PHENYL)-ACETIC ACID
• AMINO-(4-CHLORO-PHENYL)-ACETIC ACID,(S)-AMINO-(4-CHLORO-PHENYL)-ACETIC ACID
• AMINO-(4-CHLORO-PHENYL)-ACETIC ACID
• N-Boc-amino-(4-chloro-phenyl)-acetic acid
• AMINO-(4-CHLORO-PHENYL)-ACETIC ACID
• (R)-AMINO-(4-CHLORO-PHENYL)-ACETIC ACID
• AMINO-(4-CHLORO-PHENYL)-ACETIC ACID METHYL ESTER
• AMINO-(2-CHLORO-PHENYL)-ACETIC ACID HCL
• (S)-AMINO-(2-CHLORO-PHENYL)-ACETIC ACID HYDROCHLORIDE
• (R)-AMINO-(3-CHLORO-PHENYL)-ACETIC ACID
• AMINO-(3-CHLORO-PHENYL)-ACETIC ACID HCL
• 1-(4-Amino-3-chloro-phenyl)-acetic acid
• (R)-Amino-(2-chloro-phenyl)-acetic acid hydrochloride
• 1-(4-Amino-2-chloro-phenyl)-acetic acid