S-Phenyl-N-acetylcysteine

Base Information

• Chemical Name: S-Phenyl-N-acetylcysteine
• CAS No.: 4775-80-8
• Molecular Formula: C11H13NO3S
• Molecular Weight: 239.295
• Hs Code.: 2930909090
• European Community (EC) Number: 875-018-2
• UNII: 74XI8247P0
• DSSTox Substance ID: DTXSID10905052
• Nikkaji Number: J257.511F
• Wikidata: Q27077068
• NCI Thesaurus Code: C107142
• Mol file: 4775-80-8.mol

Synonyms:2-acetamido-3-phenylthiopropanoic acid;phenylmercapturic acid;S-phenyl-N-acetylcysteine;S-phenyl-N-acetylcysteine, (DL)-isomer;S-phenylmercapturic acid

Chemical Property of S-Phenyl-N-acetylcysteine

Chemical Property:

• Vapor Pressure: 1.35E-10mmHg at 25°C
• Melting Point: 110-112oC
• Boiling Point: 494.5°C at 760 mmHg
• PKA: 3.25±0.10(Predicted)
• Flash Point: 252.9°C
• PSA: 74.63000
• Density: 1.28±0.1 g/cm3(Predicted)
• LogP: 1.84220
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO (Slightly), Ethanol (Sparingly), Methanol (Slightly)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 239.06161445
• Heavy Atom Count: 16
• Complexity: 252

Purity/Quality:

99%, ^*data from raw suppliers

S-Phenylmercapturic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: CC(=O)NC(CSC1=CC=CC=C1)C(=O)O
• Isomeric SMILES: CC(=O)N[C@@H](CSC1=CC=CC=C1)C(=O)O

Technology Process of S-Phenyl-N-acetylcysteine

There total 7 articles about S-Phenyl-N-acetylcysteine 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%

iodobenzene (591-50-4) + N-acetylcystein (616-91-1,7696-05-1) → (R)-2-acetamido-3-(phenylthio)propanoic acid (4775-80-8)

Guidance literature:

iodobenzene; N-acetylcystein; 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: 75.0%

N-acetylcystein (616-91-1,7696-05-1) + benzenediazonium tetrafluoroborate (369-57-3) → (R)-2-acetamido-3-(phenylthio)propanoic acid (4775-80-8)

Guidance literature:

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

DOI:10.1021/acs.joc.7b03160

Reference yield:

N-acetylcystein (616-91-1,7696-05-1) + phenylboronic acid (98-80-6) → (R)-2-acetamido-3-(phenylthio)propanoic acid (4775-80-8) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

With copper diacetate; In aq. buffer; at 37 ℃; for 0.5h; pH=7.4; Reagent/catalyst;

DOI:10.1021/acs.orglett.1c01624

upstream raw materials:

N-acetylcystein

S-(4-Bromophenyl)mercapturic acid

(R)-2-acetamido-3-((4-bromophenyl)thio)propanoic acid

S-phenyl-L-cysteine

Downstream raw materials:

2-(S)-amino-3-phenylsulfanylpropionic acid

acetic acid

(R)-2-Acetylamino-3-benzenesulfinyl-N-benzyl-propionamide

Refernces

• 1、 Naveen, Naganaboina,Sengupta, Saumitra,Chandrasekaran, Srinivasan. "Metal-free S-arylation of cysteine using arenediazonium salts". . p. 3562 - 3569. Retrieved 2018/04/14.
• 2、 Hickman,Christie,Guy,White. "Synthesis of aromatic S-substituted derivatives of N-acetyl-L-cysteine". . p. 899 - 904. Retrieved 2007/10/02.