(r)-2-Amino-2-(4-chlorophenyl)acetic acid

Base Information

• Chemical Name: (r)-2-Amino-2-(4-chlorophenyl)acetic acid
• CAS No.: 43189-37-3
• Molecular Formula: C8H8ClNO2
• Molecular Weight: 185.61
• Hs Code.: 2922499990
• European Community (EC) Number: 674-625-8
• UNII: 5QED7UA2ML
• DSSTox Substance ID: DTXSID00353306
• Nikkaji Number: J514.074I
• Mol file: 43189-37-3.mol

Synonyms:43189-37-3;(r)-2-amino-2-(4-chlorophenyl)acetic acid;(R)-4-Chlorophenylglycine;D-4-Chlorophenylglycine;H-D-Phg(4-Cl)-OH;(2R)-2-amino-2-(4-chlorophenyl)acetic acid;(r)-4-chlorophenyl glycine;(R)-2-(4-CHLOROPHENYL)GLYCINE;MFCD03839815;(R)-Amino-(4-chloro-phenyl)-acetic acid;5QED7UA2ML;d-(4-chlorophenyl)glycine;D-4-CL-PHG-OH;(4-Chlorophenyl)glycine, D-;SCHEMBL2896976;DTXSID00353306;AKOS015853836;(r)-amino-(4-chlorophenyl)acetic acid;CS-W022748;HY-W042008;(2R)-amino(4-chlorophenyl)ethanoic acid;DS-13387;(alphaR)-alpha-Amino-4-chlorobenzeneacetic acid;alpha-Amino-4-chlorobenzeneacetic acid, (alphaR)-;Benzeneacetic acid, alpha-amino-4-chloro-, (R)-;J-300371;BENZENEACETIC ACID, ALPHA-AMINO-4-CHLORO-, (ALPHAR)-

Chemical Property of (r)-2-Amino-2-(4-chlorophenyl)acetic acid

Chemical Property:

• Vapor Pressure: 7.45E-05mmHg at 25°C
• Refractive Index: 1.603
• Boiling Point: 328.8 °C at 760 mmHg
• PKA: 1.81±0.10(Predicted)
• Flash Point: 152.7 °C
• PSA: 63.32000
• Density: 1.393 g/cm³
• LogP: 2.12470
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 185.0243562
• Heavy Atom Count: 12
• Complexity: 166

Purity/Quality:

99% ^*data from raw suppliers

(R)-4-Chlorophenylglycine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(C(=O)O)N)Cl
• Isomeric SMILES: C1=CC(=CC=C1[C@H](C(=O)O)N)Cl
• Uses: (R)-4-Chlorophenylglycine

Technology Process of (r)-2-Amino-2-(4-chlorophenyl)acetic acid

There total 16 articles about (r)-2-Amino-2-(4-chlorophenyl)acetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

4-chlorobenzaldehyde (104-88-1) → (R)-2-amino-2-(4-chlorophenyl)acetic acid (43189-37-3,7292-70-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / acetic acid / propan-2-ol

2: tin tetrachloride / triethylamine / CH₂Cl₂ / -18 °C

3: HCl / formic acid / 20 °C

With hydrogenchloride; tin(IV) chloride; acetic acid; triethylamine; In formic acid; dichloromethane; isopropyl alcohol; 2: Strecker reaction;

DOI:10.1080/00304940509355402

Reference yield:

(3R,5S,6R)-2,3,5,6-Tetrahydro-3-(p-chlorophenyl)-5,6-diphenyl-1,4-oxazin-2-one (144744-27-4) → (S)-2-amino-2-(4-chlorophenyl)acetic acid (67336-19-0,7292-70-8) + (R)-2-amino-2-(4-chlorophenyl)acetic acid (43189-37-3,7292-70-8)

Guidance literature:

With hydrogen; palladium dichloride; In tetrahydrofuran; ethanol; for 1h; under 760 Torr; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00051a044

Reference yield:

(R)-2-Amino-N-tert-butyl-2-(4-chloro-phenyl)-acetamide; hydrochloride (119825-44-4) → (R)-2-amino-2-(4-chlorophenyl)acetic acid (43189-37-3,7292-70-8)

Guidance literature:

With hydrogenchloride; In water; at 80 ℃; Yield given;

DOI:10.1016/S0040-4020(01)86054-3

upstream raw materials:

(R)-Amino-(4-chloro-phenyl)-acetic acid methylester

chloroform

4-chlorobenzaldehyde

(R)-2-Amino-N-tert-butyl-2-(4-chloro-phenyl)-acetamide; hydrochloride

Downstream raw materials:

C₂₃H₁₈ClNO₄

(1R,2R)-2-amino-1-(3-chlorophenyl)-2-(4-chlorophenyl)ethanol hydrochloride

tert-butyl (1R,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)-2-hydroxyethylcarbamate

tert-butyl (1R,2R)-2-(3-chloro-5-fluorophenyl)-1-(4-chlorophenyl)-2-hydroxyethylcarbamate

Refernces

• 1、 Qiu, Jian,Su, Erzheng,Wang, Wei,Wei, Dongzhi. "High yield synthesis of d-phenylglycine and its derivatives by nitrilase mediated dynamic kinetic resolution in aqueous-1-octanol biphasic system". . p. 1448 - 1451. Retrieved 2014/03/21.
• 2、 Zhou, Guobin,Zhang, Pengfei,Pan, Yuanjiang,Guo, Junli. "Stereoselective synthesis of α-amino acids from O-pivaloyl-D- glucopyranosylaldimine". . p. 65 - 73. Retrieved 2007/10/03.