Dimethyl bromofumarate

Base Information

• Chemical Name: Dimethyl bromofumarate
• CAS No.: 2509-16-2
• Molecular Formula: C6H7 Br O4
• Molecular Weight: 223.023
• ChEMBL ID: CHEMBL3247958
• Nikkaji Number: J740.170A
• NSC Number: 283426
• Mol file: 2509-16-2.mol

Synonyms:Dimethyl bromofumarate;2509-16-2;2-Butenedioic acid, 2-bromo-, dimethyl ester, (Z)-;NSC 283426;dimethyl (Z)-2-bromobut-2-enedioate;SCHEMBL4250455;SCHEMBL4250519;CHEMBL3247958;YFHHDQFGPGNXRZ-ARJAWSKDSA-N;NSC283426;NSC-283426;Dimethyl (2Z)-2-bromo-2-butenedioate #;2-Butenedicarbonic acid,-2-bromo, dimethyl ester;2-Butenedioic acid, 2-bromo-, dimethyl ester, (2Z)-

Chemical Property of Dimethyl bromofumarate

Chemical Property:

• Vapor Pressure: 0.0602mmHg at 25°C
• Boiling Point: 232.1°Cat760mmHg
• Flash Point: 94.1°C
• Density: 1.58g/cm³
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 221.95277
• Heavy Atom Count: 11
• Complexity: 197

Purity/Quality:

99%min ^*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)Br
• Isomeric SMILES: COC(=O)/C=C(/C(=O)OC)\Br

Technology Process of Dimethyl bromofumarate

There total 7 articles about Dimethyl bromofumarate 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%

dimethyl acetylenedicarboxylate (762-42-5) → trans-2-bromobutenedioic acid dimethyl ester (2509-16-2)

Guidance literature:

With trifluoroacetic acid; at 60 ℃; for 4h;

DOI:10.3184/030823407X200038

Reference yield:

dibromo-2,3 succinate de methyle threo racemique (1186-98-7,17582-64-8,51575-86-1) → trans-2-bromobutenedioic acid dimethyl ester (2509-16-2) + methyl 3-hydroxy-5-isoxazolecarboxylate (10068-07-2)

Guidance literature:

With 4-methyl-morpholine; N-hydroxyurea; In methanol; for 24h; Yield given. Yields of byproduct given; Ambient temperature;

Reference yield:

dibromo-2,3 succinate de methyle threo racemique (1186-98-7,17582-64-8,51575-86-1) + N-hydroxyurea (127-07-1) → trans-2-bromobutenedioic acid dimethyl ester (2509-16-2) + methyl 3-hydroxy-5-isoxazolecarboxylate (10068-07-2)

Guidance literature:

With triethylamine; In methanol; for 24h; Product distribution; Ambient temperature; further dicarboxylic acids; various bases;

upstream raw materials:

methanol

cis-2-bromobutenedioic acid

dimethyl 2-bromofumarate

dibromo-2,3 succinate de methyle threo racemique

Downstream raw materials:

methyl 3-hydroxy-5-isoxazolecarboxylate

tetraethylammonium bromide

dimethyl diethylaminofumarate

dimethyl (E)-2-(2-nitrophenoxy)-2-butenedioate

Refernces

• 1、 Bennouna, Chakib,Petrus, Francoise,Verducci, Jean. "Action de l'hydroxyuree sur des γ-diesters". . p. 478 - 480. Retrieved 2007/10/02.