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L-2-Chlorophenylglycine

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L-2-Chlorophenylglycine manufacturers

L-2-Chlorophenylglycine Basic information
Product Name:L-2-Chlorophenylglycine
Synonyms:(S)-AMINO-(2-CHLORO-PHENYL)-ACETIC ACID;(S)-(+)-ALPHA-AMINO-(2-CHLOROPHENYL)ACETIC ACID;(S)-(+)-A-AMINO-(2-CHLOROPHENYL)ACETIC ACID;(S)-(+)-2-CHLOROPHENYLGLYCINE;S-(+)-2-(2-CHLORO PHENYL)GLYCINE;L-(+)-2-CHLOROPHENYLGLYCINE;L-(2-CHLOROPHENYL)GLYCINE;(L)-(-)-ALPHA-AMINO-(2-CHLOROPHENYL)ACETIC ACID
CAS:141315-50-6
MF:C8H8ClNO2
MW:185.61
EINECS:604-231-3
Product Categories:Amino ACIDS SERIES;pharmacetical;chiral
Mol File:141315-50-6.mol
L-2-Chlorophenylglycine Structure
L-2-Chlorophenylglycine Chemical Properties
Melting point 182-187 °C(lit.)
Boiling point 318.8±32.0 °C(Predicted)
density 1.392±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
pka1.69±0.10(Predicted)
form Solid
color White to off-white
Optical Rotation[α]/D 79.0 to 90.0°, c =1 in methanol
[α]20/D +79°, c =1% in chloroform
Major Applicationpeptide synthesis
InChI1S/C8H8ClNO2/c9-6-4-2-1-3-5(6)7(10)8(11)12/h1-4,7H,10H2,(H,11,12)/t7-/m0/s1
InChIKeyLMIZLNPFTRQPSF-ZETCQYMHSA-N
SMILESN[C@H](C(O)=O)c1ccccc1Cl
CAS DataBase Reference141315-50-6(CAS DataBase Reference)
Safety Information
WGK Germany 3
HS Code 2922498590
Storage Class13 - Non Combustible Solids
Hazard ClassificationsAquatic Chronic 4
MSDS Information
ProviderLanguage
SigmaAldrich English
L-2-Chlorophenylglycine Usage And Synthesis
Chemical Propertieswhite to light yellow crystal powder
UsesL-2-Chlorophenylglycine
Synthesis
Sodium cyanide

143-33-9

2-Chlorobenzaldehyde

89-98-5

D-(+)-(2-Chlorophenyl)glycine

86169-24-6

The general procedure for the synthesis of (R)-2-amino-2-(2-chlorophenyl)acetic acid from sodium cyanide and o-chlorobenzaldehyde is as follows: 2-chlorophenylglycine was prepared according to the synthetic method described in Scheme 1. This was done as follows: 2-chlorobenzaldehyde, ammonium bicarbonate (NH4HCO3; 23.7 g) and sodium cyanide (NaCN; 14.7 g) were dissolved in a mixed solution 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).Subsequently, the precipitate was collected by filtration and washed with distilled water to give a final product of 27 g (58% yield) of 2-chlorophenylglycine. The compound had a specific optical rotation of +0.16 (C=1, 1N HCl) and a melting point of 185.4-186.8 °C.

References[1] Patent: US2004/176637, 2004, A1. Location in patent: Page 3
L-2-Chlorophenylglycine Preparation Products And Raw materials
Raw materialsSodium cyanide-->2-Chlorobenzaldehyde-->Sodium hydroxide-->Ammonium bicarbonate-->Sulfuric acid
Preparation Products(S)-2-Chlorophenylglycinol
Tag:L-2-Chlorophenylglycine(141315-50-6) Related Product Information
Ethyl 2-(Chlorosulfonyl)acetate 2-Chlorobenzoic acid 4-Hydroxy-D-(-)-2-phenylglycine 2-Chlorobenzoyl chloride 2-(2-Chlorophenyl)acetonitrile 2-Chlorophenol 2'-Chloroacetophenone Sodium glycinate 2-Chlorobenzonitrile 2-Chlorobenzaldehyde L-Phenylglycine 6-Aminocaproic acid 4-Aminophenylacetic acid Glycine α-Lipoic Acid Aminoethoxyvinyl glycine hydrochloride D-2-Phenylglycine Sodium hydroxymethylglycinate