479074-63-0

Basic information

• Product Name: (R)-3-Amino-3-(4-bromophenyl)propionic acid
• Synonyms: (βR)-β-amino-4-bromo-Benzenepropanoic acid;(R)-3-(P-BROMOPHENYL)-BETA-ALANINE ;H-D-b-Phe(4-Br)-OH;(R)-beta-(4-Bromophenyl)alanine;(R)-3-Amino-3-(4-bromophenyl)propionic acid;REF DUPL: (R)-beta-(4-bromophenyl)alanine;-R-4-Bromophenylalanine;Benzenepropanoic acid, .beta.-amino-4-bromo-, (.beta.R)-
• CAS NO: 479074-63-0
• Molecular Formula: C₉H₁₀BrNO₂
• Molecular Weight: 244.09
• Mol File: 479074-63-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 258-260 °C(Solv: water (7732-18-5); acetone (67-64-1))
• Boiling Point: 378.1 °C at 760 mmHg
• Flash Point: 182.5 °C
• Appearance: /
• Density: 1.585g/cm³
• Vapor Pressure: 2.17E-06mmHg at 25°C
• Refractive Index: 1.607
• Storage Temp.: 2-8°C(protect from light)
• PKA: 3.62±0.10(Predicted)
• CAS DataBase Reference: (R)-3-Amino-3-(4-bromophenyl)propionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-Amino-3-(4-bromophenyl)propionic acid(479074-63-0)
• EPA Substance Registry System: (R)-3-Amino-3-(4-bromophenyl)propionic acid(479074-63-0)

Safety Data

• Hazardous Substances Data: 479074-63-0(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C9H10BrNO2/c10-7-3-1-6(2-4-7)8(11)5-9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m1/s1

Upstream product

• 1122-91-4 4-bromo-benzaldehyde 
• 39773-47-2 3-amino-3-(4'-bromophenyl)propanoic acid 
• 1200-07-3 trans-4-bromocinnamic acid 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 103247-89-8 (+/-)-4-(4-bromophenyl)-2-azetidinone 

Relevant articles and documents

Kinetic Resolution of Aromatic β-Amino Acids Using a Combination of Phenylalanine Ammonia Lyase and Aminomutase Biocatalysts

An enzymatic strategy for the preparation of (R)-β-arylalanines employing phenylalanine aminomutase and ammonia lyase (PAM and PAL) enzymes has been demonstrated. Candidate PAMs with the desired (S)-selectivity from Streptomyces maritimus (EncP) and Bacillus sp. (PabH) were identified via sequence analysis using a well-studied template sequence. The newly discovered PabH could be linked to the first ever proposed biosynthesis of pyloricidin-like secondary metabolites and was shown to display better β-lyase activity in many cases. In spite of this, a method combining the higher conversion of EncP with a strict α-lyase from Anabaena variabilis (AvPAL) was found to be more amenable, allowing kinetic resolution of five racemic substrates and a preparative-scale reaction with >98% (R) enantiomeric excess. This work represents an improved and enantiocomplementary method to existing biocatalytic strategies, allowing simple product separation and modular telescopic combination with a preceding chemical step using an achiral aldehyde as starting material. (Figure presented.).

Phenylalanine aminomutase-catalyzed addition of ammonia to substituted cinnamic acids: A route to enantiopure α- and β-amino acids

(Chemical Equation Presented) An approach is described for the synthesis of aromatic α- and β-amino acids that uses phenylalanine aminomutase to catalyze a highly enantioselective addition of ammonia to substituted cinnamic acids. The reaction has a broad scope and yields substituted α- and β-phenylalanines with excellent enantiomeric excess. The regioselectivity of the conversion is determined by substituents present at the aromatic ring. A box model for the enzyme active site is proposed, derived from the influence of the hydrophobicity of substituents on the enzyme affinity toward various substrates.