4-Bromo-L-phenylalanine

Base Information

• Chemical Name: 4-Bromo-L-phenylalanine
• CAS No.: 24250-84-8
• Molecular Formula: C9H10BrNO2
• Molecular Weight: 244.088
• Hs Code.: 2922499990
• European Community (EC) Number: 634-793-5
• Nikkaji Number: J304B
• Mol file: 24250-84-8.mol

Synonyms:4-bromophenylalanine;4-bromophenylalanine, (DL)-isomer;4-bromophenylalanine, (L)-isomer;p-Br-Phe;p-Br-phenylalanine;para-bromophenylalanine

Chemical Property of 4-Bromo-L-phenylalanine

Chemical Property:

• Vapor Pressure: 6.06E-07mmHg at 25°C
• Melting Point: ~265 °C (dec.)
• Boiling Point: 368.4 °C at 760 mmHg
• PKA: 2.18±0.10(Predicted)
• Flash Point: 176.6 °C
• PSA: 63.32000
• Density: 1.588 g/cm³
• LogP: 2.10380
• Storage Temp.: Store at RT.
• Solubility.: Methanol (Slightly, Sonicated), Water (Slightly, Heated, Sonicated)
• XLogP3: -0.4
• 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

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

Safty Information:

• Pictogram(s): Xi,T
• Hazard Codes: T,Xi
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CC(C(=O)O)N)Br
• Isomeric SMILES: C1=CC(=CC=C1C[C@@H](C(=O)O)N)Br

Technology Process of 4-Bromo-L-phenylalanine

There total 26 articles about 4-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: 75.0%

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → H-p-BrPhe-OH (24250-84-8)

Guidance literature:

With sulfuric acid; for 2h; Cooling with ice;

DOI:10.2174/1570180812666141206001604

Reference yield: 68.4%

N-acetyl-4-bromophenylalanine (171095-12-8,273730-59-9) → H-p-BrPhe-OH (24250-84-8)

Guidance literature:

With hydrogenchloride; In water; at 95 - 100 ℃; for 6h;

DOI:10.1080/00397911.2012.748075

Reference yield: 58.0%

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → (S)-2-amino-3-(2-bromophenyl)propanoic acid (42538-40-9) + H-p-BrPhe-OH (24250-84-8)

Guidance literature:

With bromoisocyanuric acid monosodium salt; sulfuric acid; at 0 ℃; for 2h;

DOI:10.1248/cpb.54.1715

upstream raw materials:

N-trifluoroacetyl-p-bromo-DL-phenylalanine

tert-butyl (2S,5S)-5-(4-bromobenzyl)-2-(tert-butyl)-3-methyl-4-oxo-1-imidazolidinecarboxylate

L-phenylalanine

p-bromo-DL-phenylalanine

Downstream raw materials:

(S)-2-(benzyloxycarbonylamino)-3-(4-bromophenyl)propanoic acid

(2S)-amino-3-(4'-phenoxy-biphenyl-4-yl)-propionic acid methyl ester hydrochloride salt

(2S)-amino-3-(2'-phenoxy-biphenyl-4-yl)-propionic acid methyl ester hydrochloride salt

2-phenoxy-biphenyl alanine

Refernces

• 1、 Walton, Curtis J. W.,Parmeggiani, Fabio,Barber, Janet E. B.,McCann, Jenna L.,Turner, Nicholas J.,Chica, Roberto A.. "Engineered Aminotransferase for the Production of d-Phenylalanine Derivatives Using Biocatalytic Cascades". . p. 470 - 474. Retrieved 2017/12/15.
• 2、 Khorsand, Fahimeh,Murphy, Cormac D.,Whitehead, Andrew J.,Engel, Paul C.. "Biocatalytic stereoinversion of d-: Para -bromophenylalanine in a one-pot three-enzyme reaction". supporting information. p. 503 - 510. Retrieved 2017/08/14.