3-Bromo-l-phenylalanine

Base Information

• Chemical Name: 3-Bromo-l-phenylalanine
• CAS No.: 82311-69-1
• Molecular Formula: C9H10BrNO2
• Molecular Weight: 244.088
• Hs Code.: 2922499990
• European Community (EC) Number: 672-536-9
• DSSTox Substance ID: DTXSID50376126
• Nikkaji Number: J3.470.931I
• Wikidata: Q72449193
• ChEMBL ID: CHEMBL3809682
• Mol file: 82311-69-1.mol

Synonyms:3-bromo-l-phenylalanine;82311-69-1;(s)-2-amino-3-(3-bromophenyl)propanoic acid;h-phe(3-br)-oh;L-3-Bromophenylalanine;(2S)-2-amino-3-(3-bromophenyl)propanoic acid;L-Phenylalanine, 3-bromo-;3-Bromophenylalanine;l-3-bromophe;(S)-2-amino-3-(3'-bromophenyl)propanoic acid;L-3-BR-PHE-OH;MFCD06659110;3-Bromo-Phe-OH;(S)-2-AMINO-3-(3-BROMOPHENYL)PROPIONIC ACID;3-bromo-phenylalanine;(L)-Bromophenyl alanine;(s)-3-bromophenylalanine;(l)-3-bromophenyl alanine;SCHEMBL44027;CHEMBL3809682;AMY4445;DTXSID50376126;GDMOHOYNMWWBAU-QMMMGPOBSA-N;AKOS012010389;AC-5854;CS-W008183;FS-1311;HY-W008183;PD196538;A5332;EN300-384090;J-300373;(S)-2-amino-3-(3-bromophenyl)propanoic acid;(S)-3-(3-BROMOPHENYL)-BETA-ALANINE

Chemical Property of 3-Bromo-l-phenylalanine

Chemical Property:

• Boiling Point: 368.4 °C at 760 mmHg
• PKA: 2.16±0.10(Predicted)
• Flash Point: 176.6 °C
• PSA: 63.32000
• Density: 1.588 g/cm³
• LogP: 2.10380
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Slightly soluble in water.
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 242.98949
• Heavy Atom Count: 13
• Complexity: 187

Purity/Quality:

3-Bromo- L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)Br)CC(C(=O)O)N
• Isomeric SMILES: C1=CC(=CC(=C1)Br)C[C@@H](C(=O)O)N
• Uses: 3-Bromo-L-phenylalanine is used in preparation of lifitegrast intermediate. It is applied in the facile removal of leader peptides from lanthipeptides by incorporation of a hydroxy acid.

Technology Process of 3-Bromo-l-phenylalanine

There total 11 articles about 3-Bromo-l-phenylalanine 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: 89.0%

(2S)-3-(3-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid (82278-73-7) → (S)-2-amino-3-(3-bromophenyl)propanoic acid (82311-69-1,99295-78-0)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 16h;

Reference yield:

2-amino-3-(3-bromophenyl)propanoic acid (30163-20-3,99295-78-0) → (2R)-2-amino-3-(3-bromophenyl)propanoic acid (99295-78-0) + (S)-2-amino-3-(3-bromophenyl)propanoic acid (82311-69-1,99295-78-0)

Guidance literature:

With phenylalanine ammonia-lyase from Pseudozyma antarctica yeast; In aq. buffer; at 30 ℃; for 168h; pH=8.5; Time; stereoselective reaction; Resolution of racemate;

DOI:10.1016/j.cattod.2020.04.002

Reference yield:

(S)-3-(3-bromobenzyl)-2-diphenylimine glycine tert-butyl ester → (S)-2-amino-3-(3-bromophenyl)propanoic acid (82311-69-1,99295-78-0)

Guidance literature:

With hydrogenchloride; In water; at 100 ℃; for 3h;

DOI:10.1016/j.bmc.2018.03.023

upstream raw materials:

(2S)-3-(3-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid

3-Bromocinnamic acid

3-bromocinnamic acid

m-bromobenzoic aldehyde

Downstream raw materials:

(2S)-3-(3-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid

Refernces

• 1、 Meng, Kaicheng,Shim, Paul,Wang, Qingtin,Zhao, Shuai,Gu, Ting,Kahsai, Alem W.,Ahn, Seungkirl,Chen, Xin. "Design, synthesis, and functional assessment of Cmpd-15 derivatives as negative allosteric modulators for the β2-adrenergic receptor". . p. 2320 - 2330. Retrieved 2018/03/29.
• 2、 Rowles, Ian,Groenendaal, Bas,Binay, Baris,Malone, Kirk J.,Willies, Simon C.,Turner, Nicholas J.. "Engineering of phenylalanine ammonia lyase from Rhodotorula graminis for the enhanced synthesis of unnatural L-amino acids". . p. 7343 - 7347. Retrieved 2016/10/30.