Dimethyl chlorofumarate

Base Information

• Chemical Name: Dimethyl chlorofumarate
• CAS No.: 5331-33-9
• Molecular Formula: C13H17N3O3
• Molecular Weight: 178.572
• NSC Number: 2275
• DSSTox Substance ID: DTXSID001031539
• Nikkaji Number: J192.712D,J41.598G
• Wikidata: Q76304640
• Mol file: 5331-33-9.mol

Synonyms:Dimethyl chlorofumarate;Dimethyl 2-chlorofumarate;5331-33-9;NSC 2275;Dimethyl chlorobutenedioate;Dimethyl (Z)-2-chloro-2-butenedioate;CP 3854;2-Butenedioic acid, 2-chloro-, dimethyl ester, (Z)-;Chlorofumaric acid dimethyl ester;C6-H7-Cl-O4;Fumaric acid, chloro-, dimethyl ester;2-Butenedioic acid, 2-chloro-, dimethyl ester, (E)-;SCHEMBL4250392;SCHEMBL4250395;NSC2275;VYXGXXYXSAMWBM-ARJAWSKDSA-N;DTXSID001031539;NSC-2275;TL-407;LS-46988;(Z)-2-chloro-but-2-enedioic acid dimethyl ester;2-CHLORO-TRANS-2-BUTENEDIOIC ACID, DIMETHYL ESTER

Chemical Property of Dimethyl chlorofumarate

Chemical Property:

• Vapor Pressure: 0.0934mmHg at 25°C
• Boiling Point: 224°C at 760 mmHg
• Flash Point: 91.5°C
• Density: 1.281g/cm³
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 178.0032864
• Heavy Atom Count: 11
• Complexity: 197

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C=C(C(=O)OC)Cl
• Isomeric SMILES: COC(=O)/C=C(/C(=O)OC)\Cl

Technology Process of Dimethyl chlorofumarate

There total 5 articles about Dimethyl chlorofumarate 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: 85.0%

2-(4-methylphenylsulfonamido)acetyl chloride (56218-62-3) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl chlorofumarate (5331-33-9) + 1,4-bis[(4-methylphenyl)sulfonyl]tetrahydropyrazine-2,5-dione (95021-64-0)

Guidance literature:

With triphenylphosphine; In dichloromethane; at -5 ℃; for 2h;

DOI:10.1007/s00706-002-0533-4

Reference yield: 82.0%

1-(phenylsulphonylamino)acetyl chloride (74427-60-4) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl chlorofumarate (5331-33-9) + 1,4-bis(phenylsulfonyl)tetrahydropyrazine-2,5-dione (33295-34-0)

Guidance literature:

With triphenylphosphine; In dichloromethane; at -5 ℃; for 2h;

DOI:10.1007/s00706-002-0533-4

Reference yield: 80.0%

dimethyl acetylenedicarboxylate (762-42-5) + (4-ethyl-benzenesulfonylamino)-acetyl chloride → dimethyl chlorofumarate (5331-33-9) + 1,4-bis[(4-ethylphenyl)sulfonyl]tetrahydropyrazine-2,5-dione

Guidance literature:

With triphenylphosphine; In dichloromethane; at -5 ℃; for 2h;

DOI:10.1007/s00706-002-0533-4

upstream raw materials:

threo-dimethyl α-fluoro-α'-chlorosuccinate

2,3-Dimethyl-2-butene

dimethyl acetylenedicarboxylate

2-(4-methylphenylsulfonamido)acetyl chloride

Downstream raw materials:

r-1,t-3-bis(methoxycarbonyl)-1-chloro-t-2-methyl-c-2-phenylcyclopropane

3-chloro-r-3,t-4-bis(methoxycarbonyl)-c-5-methyl-t-5-phenyl-1-pyrazoline

1-chloro-r-1,t-3-bis(methoxycarbonyl)-c-2-methyl-t-2-phenylcyclopropane

trans-1,3-bis(methoxycarbonyl)-1-chloro-2,2-diphenylcyclopropane