| Identification | More | [Name]
AMINO-(2-CHLORO-PHENYL)-ACETIC ACID | [CAS]
88744-36-9 | [Synonyms]
2-CHLORO-DL-PHENYLGLYCINE
(+/-)-2-CHLOROPHENYLGLYCINE
2-CHLOROPHENYLGLYCINE
(+/-)-ALPHA-AMINO-2-CHLOROPHENYLACETIC ACID
AMINO-(2-CHLORO-PHENYL)-ACETIC ACID
DL 2-(2-CHLOROPHENYL)-GLYCINE
DL-2-CHLOROPHENYLGLYCINE
O-CHLORO-A-AMINOPHENYLACETIC ACID
RARECHEM AK ML 0504
alpha-Amino-o-chlorophenylacetic acid, 2-(2-Chlorophenyl)glycine | [Molecular Formula]
C8H8ClNO2 | [MDL Number]
MFCD00049324 | [Molecular Weight]
185.61 | [MOL File]
88744-36-9.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [F ]
10-23 | [HS Code ]
29224985 |
| Hazard Information | Back Directory | [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 |
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