N-Acetyl-S-(4-bromophenyl)cysteine

Base Information

• Chemical Name: N-Acetyl-S-(4-bromophenyl)cysteine
• CAS No.: 3343-66-6
• Molecular Formula: C₁₁H₁₂BrNO₃S
• Molecular Weight: 318.191
• UNII: 48NZ5HZ4J6
• DSSTox Substance ID: DTXSID70944063
• Nikkaji Number: J386.933D
• Wikidata: Q27259158
• Mol file: 3343-66-6.mol

Synonyms:P-BPMA;para-bromophenylmercapturic acid;S-(4-bromophenyl)mercapturic acid

Chemical Property of N-Acetyl-S-(4-bromophenyl)cysteine

Chemical Property:

• Vapor Pressure: 2.7E-12mmHg at 25°C
• Boiling Point: 535.4°C at 760 mmHg
• Flash Point: 277.6°C
• PSA: 91.70000
• Density: 1.59g/cm³
• LogP: 2.52140
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 316.97213
• Heavy Atom Count: 17
• Complexity: 280

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CSC1=CC=C(C=C1)Br)C(=O)O
• Isomeric SMILES: CC(=O)N[C@@H](CSC1=CC=C(C=C1)Br)C(=O)O

Technology Process of N-Acetyl-S-(4-bromophenyl)cysteine

There total 8 articles about N-Acetyl-S-(4-bromophenyl)cysteine 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: 99.0%

N-acetylcystein (616-91-1,7696-05-1) + 1,4-bromoiodobenzene (589-87-7) → (R)-2-acetamido-3-((4-bromophenyl)thio)propanoic acid (21462-47-5,3343-66-6)

Guidance literature:

N-acetylcystein; 1,4-bromoiodobenzene; With C₅₃H₄₆NO₄PPdS; In tetrahydrofuran; at 20 ℃; for 0.0166667h; Schlenk technique;

With triethylamine; In tetrahydrofuran; at 20 ℃; for 0.0833333h; chemoselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1002/chem.201602277

Reference yield: 87.0%

N-Acetamidoacrylic acid (5429-56-1) + para-bromobenzenethiol (106-53-6) → S-(4-Bromophenyl)mercapturic acid (126253-78-9,3343-66-6)

Guidance literature:

With piperidine; In 1,4-dioxane; for 3h; Heating;

DOI:10.1021/jo00296a034

Reference yield: 69.0%

N-acetylcystein (616-91-1,7696-05-1) + 4-bromobenzenediazonium tetrafluoroborate (673-40-5) → (R)-2-acetamido-3-((4-bromophenyl)thio)propanoic acid (21462-47-5,3343-66-6)

Guidance literature:

With sodium methylate; In methanol; at 0 - 15 ℃; for 3h; chemoselective reaction;

DOI:10.1021/acs.joc.7b03160

upstream raw materials:

S-(4-bromo-phenyl)-cysteine

acetic anhydride

benzene

N-Acetamidoacrylic acid

Downstream raw materials:

(R)-2-acetamido-3-(phenylthio)propanoic acid

S-(4-bromo-phenyl)-cysteine

Refernces

• 1、 Al-Shuaeeb, Riyadh Ahmed Atto,Kolodych, Sergii,Koniev, Oleksandr,Delacroix, Sébastien,Erb, Stéphane,Nicola?, Stéphanie,Cintrat, Jean-Christophe,Brion, Jean-Daniel,Cianférani, Sarah,Alami, Mouad,Wagner, Alain,Messaoudi, Samir. "Palladium-Catalyzed Chemoselective and Biocompatible Functionalization of Cysteine-Containing Molecules at Room Temperature". supporting information. p. 11365 - 11370. Retrieved 2016/08/03.