(S)-N-acetyl-4-bromophenylalanine

Base Information

• Chemical Name: (S)-N-acetyl-4-bromophenylalanine
• CAS No.: 171095-12-8
• Molecular Formula: C₁₁H₁₂BrNO₃
• Molecular Weight: 286.125
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID90425127
• Nikkaji Number: J2.568.941K
• Wikidata: Q82237883
• Mol file: 171095-12-8.mol

Synonyms:171095-12-8;(S)-N-acetyl-4-bromophenylalanine;N-Acetyl-4-bromo-L-phenylalanine;(2S)-2-acetamido-3-(4-bromophenyl)propanoic acid;(S)-2-Acetamido-3-(4-bromophenyl)propanoic acid;(2S)-3-(4-bromophenyl)-2-acetamidopropanoic acid;2-(Acetylamino)-3-(4-Bromophenyl)Propanoic Acid;Maybridge1_008975;N-acetyl-4-bromophenylalanine;Oprea1_081241;SCHEMBL12813228;HMS566P21;DTXSID90425127;MFCD03094633;CCG-255264;AS-33369;CS-0207013;(S)-N-acetyl-4-bromophenylalanine, AldrichCPR;(S)-2-Acetamido-3-(4-bromophenyl)propanoicacid;EN300-7401487

Chemical Property of (S)-N-acetyl-4-bromophenylalanine

Chemical Property:

• Vapor Pressure: 4.07E-11mmHg at 25°C
• Melting Point: 191-193oC
• Boiling Point: 507.4oC at 760 mmHg
• PKA: 3.51±0.10(Predicted)
• Flash Point: 260.7oC
• PSA: 66.40000
• Density: 1.514g/cm3
• LogP: 1.97180
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 285.00006
• Heavy Atom Count: 16
• Complexity: 262

Purity/Quality:

99% ^*data from raw suppliers

N-Acetyl-4-bromo-L-phenylalanine 95.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CC1=CC=C(C=C1)Br)C(=O)O
• Isomeric SMILES: CC(=O)N[C@@H](CC1=CC=C(C=C1)Br)C(=O)O

Technology Process of (S)-N-acetyl-4-bromophenylalanine

There total 13 articles about (S)-N-acetyl-4-bromophenylalanine 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: 42.0%

ethyl 4-bromo-N-acetylphenylalaninate (140202-28-4) → (D)-N-acetyl-4-bromo-phenylalanine ethyl ester + N-acetyl-4-bromophenylalanine (171095-12-8,273730-59-9)

Guidance literature:

With water; In ethanol; at 25 ℃; for 3h; optical yield given as %ee; enantioselective reaction; Microbiological reaction;

DOI:10.1016/j.tetasy.2010.02.011

Reference yield:

p-bromo-DL-phenylalanine (14091-15-7) + acetic anhydride (108-24-7) → N-acetyl-4-bromophenylalanine (171095-12-8,273730-59-9)

Guidance literature:

In methanol; at 20 ℃;

DOI:10.1080/00397911.2011.562063

Reference yield:

(Z)-2-acetamido-3-(4-bromophenyl)acrylic acid → (R)-2-Acetylamino-3-(4-bromo-phenyl)-propionic acid (171095-12-8,273730-59-9) + N-acetyl-4-bromophenylalanine (171095-12-8,273730-59-9)

Guidance literature:

With (R)-spiroBIP; hydrogen; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; In methanol; toluene; at 20 ℃; for 24h; under 3800 Torr; Title compound not separated from byproducts;

DOI:10.1016/j.tetasy.2006.01.021

upstream raw materials:

ethyl 4-bromo-N-acetylphenylalaninate

4-(4-bromophenyl)methylene-2-methyl-5(4H)-oxazolone

C₁₁H₁₀BrNO₃

4-bromo-benzaldehyde

Downstream raw materials:

H-p-BrPhe-OH

Refernces

• 1、 Yang, Yihua,Liu, Shouxin,Li, Junzhang,Tian, Xia,Zhen, Xiaoli,Han, Jianrong. "Convenient method for reduction of C-N double bonds in oximes, imines, and hydrazones using sodium Borohydride-Raney ni system". . p. 2540 - 2554. Retrieved 2012/07/27.
• 2、 Stella, Selvaraj,Chadha, Anju. "Resolution of N-protected amino acid esters using whole cells of Candida parapsilosis ATCC 7330". experimental part. p. 457 - 460. Retrieved 2010/06/21.