2-Acetamido-3-(4-fluorophenyl)sulfanylpropanoic acid

Base Information

• Chemical Name: 2-Acetamido-3-(4-fluorophenyl)sulfanylpropanoic acid
• CAS No.: 331-93-1
• Molecular Formula: C11H12 F N O3 S
• Molecular Weight: 257.28
• Hs Code.: 2930909090
• DSSTox Substance ID: DTXSID90392466
• Mol file: 331-93-1.mol

Synonyms:S-(4-Fluorophenyl)mercapturic Acid;331-93-1;2-acetamido-3-(4-fluorophenyl)sulfanylpropanoic acid;p-Fluoro-S-phenylmercapturic Acid;N-Acetyl-3-[(p-fluorophenyl)thio]alanine;DTXSID90392466;AKOS013909310;FT-0668710;J-019077;2-acetamido-3-[(4-fluorophenyl)sulfanyl]propanoic acid

Chemical Property of 2-Acetamido-3-(4-fluorophenyl)sulfanylpropanoic acid

Chemical Property:

• Melting Point: 161-162°C
• PSA: 91.70000
• LogP: 1.89800
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 257.05219258
• Heavy Atom Count: 17
• Complexity: 280

Purity/Quality:

98%min ^*data from raw suppliers

S-(4-Fluorophenyl)mercapturicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CSC1=CC=C(C=C1)F)C(=O)O
• Uses: An important metabolite of Benzene An important metabolite of Benzene.

Technology Process of 2-Acetamido-3-(4-fluorophenyl)sulfanylpropanoic acid

There total 3 articles about 2-Acetamido-3-(4-fluorophenyl)sulfanylpropanoic acid 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) + 4-fluoro-1-iodobenzene (352-34-1) → (R)-2-acetamido-3-((4-fluorophenyl)thio)propanoic acid (331-93-1)

Guidance literature:

N-acetylcystein; 4-fluoro-1-iodobenzene; 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: 72.0%

N-acetylcystein (616-91-1,7696-05-1) + 4-fluorobenzenediazonium tetrafluoroborate (459-45-0) → (R)-2-acetamido-3-((4-fluorophenyl)thio)propanoic acid (331-93-1)

Guidance literature:

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

DOI:10.1021/acs.joc.7b03160

Reference yield:

S-(4-fluorophenyl)-L-cysteine (331-90-8,331-89-5) + acetic anhydride (108-24-7) → (R)-2-acetamido-3-((4-fluorophenyl)thio)propanoic acid (331-93-1)

Guidance literature:

With sodium hydroxide;

upstream raw materials:

S-(4-fluorophenyl)-L-cysteine

acetic anhydride

N-acetylcystein

4-fluoro-1-iodobenzene

Downstream raw materials:

S-(4-fluorophenyl)-L-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.