262429-49-2

Basic information

• Product Name: (R)-3-AMINO-3-(3-CHLORO-PHENYL)-PROPIONIC ACID
• Synonyms: (R)-BETA-(3-CHLOROPHENYL)ALANINE;(R)-3-AMINO-3-(3-CHLORO-PHENYL)-PROPIONIC ACID;H-D-BETA-PHE(3-CL)-OH;L-BETA-HOMO(3-CHLOROPHENYL)GLYCINE;H-PHG(3-CL)-(C*CH2)OH;(R)--(3-Chlorophenyl)alanine;(R)-3-(3-CHLOROPHENYL)-BETA-ALANINE ;(R)-3-amino-3-(3-chlorophenyl)propanoic acid
• CAS NO: 262429-49-2
• Molecular Formula: C₉H₁₀ClNO₂
• Molecular Weight: 199.63
• Product Categories: 3-Amino-3-phenylpropionic Acid Analogs;3-Amino-3-phenylpropanoic Acid Analogs;API intermediates;B-Amino
• Mol File: 262429-49-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 230-233 °C(Solv: water (7732-18-5); acetone (67-64-1))
• Boiling Point: 334.738 °C at 760 mmHg
• Flash Point: 156.244 °C
• Appearance: /
• Density: 1.333 g/cm³
• Vapor Pressure: 4.95E-05mmHg at 25°C
• Refractive Index: 1.588
• Storage Temp.: 2-8°C(protect from light)
• PKA: 3.60±0.10(Predicted)
• CAS DataBase Reference: (R)-3-AMINO-3-(3-CHLORO-PHENYL)-PROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-AMINO-3-(3-CHLORO-PHENYL)-PROPIONIC ACID(262429-49-2)
• EPA Substance Registry System: (R)-3-AMINO-3-(3-CHLORO-PHENYL)-PROPIONIC ACID(262429-49-2)

Safety Data

• Hazardous Substances Data: 262429-49-2(Hazardous Substances Data)

Usage

General Description

(R)-3-Amino-3-(3-chloro-phenyl)-propionic acid is a chemical compound that belongs to the class of organic compounds known as phenylpropanoic acids, specifically an amino acid. It has a specific structure that includes a chlorine atom attached to a phenyl group--a ring of six carbon atoms, and an amino function on the propionic acid. (R)-3-AMINO-3-(3-CHLORO-PHENYL)-PROPIONIC ACID contains a carboxylic acid group (COOH) and an amine group (NH2). Propionic acids are compounds comprising of a propionic acid moiety, which is a three-carbon carboxylic acid. The term "(R)" in its name refers to the chirality or spatial arrangement of the molecule, indicating it has a specific orientation in space, which can affect its potential biological activity. (R)-3-AMINO-3-(3-CHLORO-PHENYL)-PROPIONIC ACID may be used in the field of organic synthesis in order to design and synthesize new chemicals and materials.

InChI:InChI=1/C9H10ClNO2/c10-7-3-1-2-6(4-7)8(11)5-9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m1/s1

Upstream product

• 1866-38-2 m-Chlorocinnamic acid 
• 587-04-2 m-Chlorobenzaldehyde 
• 68208-21-9 3-amino-3-(3-chloro-phenyl)-propionic acid 
• 2039-85-2 3-Chlorostyrene 
• 262429-48-1 (+/-)-N-Phenylacetyl-3-(3-chlorophenyl)-β-alanine 

Relevant articles and documents

Enantioselective acylation of β-phenylalanine acid and its derivatives catalyzed by penicillin G acylase from alcaligenes faecalis

This study developed a simple, efficient method for producing racemic β-phenylalanine acid (BPA) and its derivatives via the enantioselective acylation catalyzed by the penicillin G acylase from Alcaligenes faecalis (Af-PGA). When the reaction was run at 25°C and pH 10 in an aqueous medium containing phenylacetamide and BPA in a molar ratio of 2:1, 8 U/mL enzyme and 0.1 M BPA, the maximum BPA conversion efficiency at 40 min only reached 36.1%, which, however, increased to 42.9% as the pH value and the molar ratio of phenylacetamide to BPA were elevated to 11 and 3:1, respectively. Under the relatively optimum reaction conditions, the maximum conversion efficiencies of BPA derivatives all reached about 50% in a relatively short reaction time (45-90 min). The enantiomeric excess value of product (eep) and enantiomeric excess value of substrate (ees) were all above 98% and 95%, respectively. These results suggest that the method established in this study is practical, effective, and environmentally benign and may be applied to industrial production of enantiomerically pure BPA and its derivatives.

A new route to enantiopure β-aryl-substituted β-amino acids and 4-aryl-substituted β-lactams through lipase-catalyzed enantioselective ring cleavage of β-lactams

A simple and efficient direct enzymatic method was developed for the synthesis of 4-aryl-substituted β-lactams and the corresponding β-amino acid enantiomers through the CAL-B (lipase B from Candida antarctica)-catalyzed enantioselective (E > 200) ring cleavage of the corresponding racemic β-lactams with 1 equiv. of H2O in i-Pr2O at 60°C. The product (R)-β-amino acids (ee ≥ 98%, yields ≥ 42%) and unreacted (S)-β-lactams (ee ≥ 95%, yields ≥ 41%) could be easily separated. The ring opening of enantiomeric β-lactams with 18% HCl afforded the corresponding enantiopure β-amino acid hydrochlorides (ee ≥ 99%).