S-(1,2-Dichlorovinyl)-L-cysteine

Base Information

• Chemical Name: S-(1,2-Dichlorovinyl)-L-cysteine
• CAS No.: 627-72-5
• Deprecated CAS: 131907-86-3,89395-03-9,29728-72-1
• Molecular Formula: C5H7 Cl2 N O2 S
• Molecular Weight: 216.088
• Hs Code.: 2930909090
• UNII: Q9M8NNK4D4
• Nikkaji Number: J86.680F
• Wikidata: Q27120672
• Metabolomics Workbench ID: 56673
• ChEMBL ID: CHEMBL2311075
• Mol file: 627-72-5.mol

Synonyms:1,2-DCVC;1,2-dichlorovinyl-L-cysteine;S-(1,2-dichlorovinyl)cysteine;S-(1,2-dichlorovinyl)cysteine, L-Cys(E)-isomer;S-(2,2-dichlorovinyl)-L-cysteine

Chemical Property of S-(1,2-Dichlorovinyl)-L-cysteine

Chemical Property:

• Vapor Pressure: 1.66E-05mmHg at 25°C
• Refractive Index: 1.6100 (estimate)
• Boiling Point: 339.7°C at 760 mmHg
• Flash Point: 159.2°C
• PSA: 88.62000
• Density: 1.544g/cm³
• LogP: 2.10830
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Methanol
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 214.9574550
• Heavy Atom Count: 11
• Complexity: 174

Purity/Quality:

99%, ^*data from raw suppliers

3-[(1,2-Dichlorovinyl)thio]-L-alanineHydrochlorideSalt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C(C(=O)O)N)SC(=CCl)Cl
• Isomeric SMILES: C([C@@H](C(=O)O)N)S/C(=C/Cl)/Cl
• Uses: A mutagenic and nephrotoxic metabolite of trichloroethylene. S-(1,2-Dichlorovinyl)-L-cysteine (DCVC) is a model nephrotoxicant and cataractogen used to induce acute renal failure and cataracts in experimental animals to study the biochemical, physiological, and molecular mechanisms underlying the disease. Hydrochloride salt of 3-[(1,2-Dichlorovinyl)thio]-L-alanine, a mutagenic and nephrotoxic metabolite of trichloroethylene.

Technology Process of S-(1,2-Dichlorovinyl)-L-cysteine

There total 2 articles about S-(1,2-Dichlorovinyl)-L-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:

N-acetyl-S-(1,2-dichlorovinyl)-L-cysteine (2148-31-4,104713-70-4) → S-(1,2.dichlorovinyl)-L-cysteine (627-72-5,131907-86-3,1948-28-3,29728-72-1)

Guidance literature:

With rat kidney acylase; In phosphate buffer; at 37 ℃; for 0.5h; pH=7.4; Enzyme kinetics; Enzymatic reaction;

DOI:10.1021/tx990090p

Reference yield:

L-Cysteine (52-90-4) + Trichloroethylene (79-01-6) → S-(1,2.dichlorovinyl)-L-cysteine (627-72-5,131907-86-3,1948-28-3,29728-72-1)

Guidance literature:

With ammonia; sodium;

Reference yield:

S-(1,2.dichlorovinyl)-L-cysteine (627-72-5,131907-86-3,1948-28-3,29728-72-1) → S-Vinyl-cystein-S-oxid (189082-79-9,189082-80-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Al-Hg, H₂O

2: aq. H₂O₂ / acetic acid

With aluminium amalgam; water; dihydrogen peroxide; In acetic acid;

upstream raw materials:

N-acetyl-S-(1,2-dichlorovinyl)-L-cysteine

L-Cysteine

Trichloroethylene

Downstream raw materials:

S-Vinyl-cystein-S-oxid

Refernces

• 1、 Uttamsingh, Vinita,Anders. "Acylase-catalyzed deacetylation of haloalkene-derived mercapturates". . p. 937 - 942. Retrieved 2007/10/03.