(r)-3-(p-Bromophenyl)-beta-alanine

Base Information

• Chemical Name: (r)-3-(p-Bromophenyl)-beta-alanine
• CAS No.: 479074-63-0
• Molecular Formula: C9H10BrNO2
• Molecular Weight: 244.088
• European Community (EC) Number: 674-636-8
• DSSTox Substance ID: DTXSID10352360
• Nikkaji Number: J1.302.437E
• Mol file: 479074-63-0.mol

Synonyms:479074-63-0;(r)-3-(p-bromophenyl)-beta-alanine;(r)-3-amino-3-(4-bromophenyl)propanoic acid;(3r)-3-amino-3-(4-bromophenyl)propanoic acid;(r)-3-amino-3-(4-bromophenyl)propionic acid;(r)-3-amino-3-(4-bromo-phenyl)-propionic acid;h-d-beta-phe(4-br)-oh;(R)-BETA-(4-BROMOPHENYL)ALANINE;R-3-Amino-3-(4-bromo-phenyl)-propionic acid;p-bromo-beta-phenylalanine;Benzenepropanoic acid, b-amino-4-bromo-, (bR)-;h-phg(4-br)-(c*ch2)oh;SCHEMBL1585565;(R)- -(p-Bromophenyl)alanine;(r)-4-bromo-beta-phenylalanine;(r)-beta-(p-bromophenyl)alanine;DTXSID10352360;RBOUYDUXPMAYMJ-MRVPVSSYSA-N;(r)-b-(p-bromophenyl)-b-alanine;MFCD03840386;AKOS010393435;(R)-b-amino-4-bromobenzenepropanoic acid;AC-22018;AS-37043;(r)-3-amino-3-(4-bromophenyl)propanoicacid;CS-0045020;EN300-93325;(r)-3-amino-3-(4-bromo-phenyl)-propanoic acid

Chemical Property of (r)-3-(p-Bromophenyl)-beta-alanine

Chemical Property:

• Vapor Pressure: 2.17E-06mmHg at 25°C
• Melting Point: 258-260 °C(Solv: water (7732-18-5); acetone (67-64-1))
• Refractive Index: 1.607
• Boiling Point: 378.1 °C at 760 mmHg
• PKA: 3.62±0.10(Predicted)
• Flash Point: 182.5 °C
• PSA: 63.32000
• Density: 1.585g/cm³
• LogP: 2.62390
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 242.98949
• Heavy Atom Count: 13
• Complexity: 179

Purity/Quality:

99% ^*data from raw suppliers

(R)-3-Amino-2-(4-bromo-phenyl)-propionic acid >97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(CC(=O)O)N)Br
• Isomeric SMILES: C1=CC(=CC=C1[C@@H](CC(=O)O)N)Br

Technology Process of (r)-3-(p-Bromophenyl)-beta-alanine

There total 5 articles about (r)-3-(p-Bromophenyl)-beta-alanine 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: 47.0%

(+/-)-4-(4-bromophenyl)-2-azetidinone (103247-89-8) → (S)-4-(4-bromophenyl)-2-azetidinone (930769-50-9) + (R)-3-amino-3-(4-bromo-phenyl)-propionic acid (479074-63-0,295356-30-8)

Guidance literature:

With CAL-B (lipase B from Candida antarctica); water; In isopropyl alcohol; at 60 ℃; for 14h;

DOI:10.1002/adsc.200505434

Reference yield:

3-amino-3-(4'-bromophenyl)propanoic acid (39773-47-2,295356-30-8) → (R)-3-amino-3-(4-bromo-phenyl)-propionic acid (479074-63-0,295356-30-8) + trans-4-bromocinnamic acid (1200-07-3,5676-63-1,17916-60-8) + H-p-BrPhe-OH (24250-84-8)

Guidance literature:

With phenylalanine 2,3-aminomutase from Pantoea agglomerans; ammonium carbonate; at 20 ℃; for 20h; pH=8; enantioselective reaction; Enzymatic reaction;

DOI:10.1039/c6ra02964g

Reference yield:

4-bromo-benzaldehyde (1122-91-4) → (R)-3-amino-3-(4-bromo-phenyl)-propionic acid (479074-63-0,295356-30-8) + trans-4-bromocinnamic acid (1200-07-3,5676-63-1,17916-60-8) + H-p-BrPhe-OH (24250-84-8)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonium formate / ethanol / 4 h / Reflux

2: phenylalanine ammonia lyase from Streptomyces maritimus; phenylalanine ammonia α-lyase from Anabaena variabilis / aq. buffer / 24 h / 30 °C / pH 8 / Resolution of racemate; Enzymatic reaction

With phenylalanine ammonia α-lyase from Anabaena variabilis; phenylalanine ammonia lyase from Streptomyces maritimus; ammonium formate; In ethanol;

DOI:10.1002/adsc.201600894

upstream raw materials:

(+/-)-4-(4-bromophenyl)-2-azetidinone

1-bromo-4-ethenyl-benzene

trans-4-bromocinnamic acid

3-amino-3-(4'-bromophenyl)propanoic acid

Refernces

• 1、 Varga, Andrea,Bánóczi, Gergely,Nagy, Botond,Bencze, László Csaba,To?a, Monica Ioana,Gellért, ákos,Irimie, Florin Dan,Rétey, János,Poppe, László,Paizs, Csaba. "Influence of the aromatic moiety in α- And β-arylalanines on their biotransformation with phenylalanine 2,3-aminomutase from: Pantoea agglomerans". . p. 56412 - 56420. Retrieved 2016/07/06.
• 2、 Forro, Eniko,Paal, Tihamer,Tasnadi, Gabor,Fueloep, Ferenc. "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". . p. 917 - 923. Retrieved 2007/10/03.