Bis(bromomethyl)maleic anhydride

Base Information

• Chemical Name: Bis(bromomethyl)maleic anhydride
• CAS No.: 479035-70-6
• Molecular Formula: C6H4Br2O3
• Molecular Weight: 283.904
• DSSTox Substance ID: DTXSID50423745
• Wikidata: Q82236010
• ChEMBL ID: CHEMBL2270564
• Mol file: 479035-70-6.mol

Synonyms:Bis(bromomethyl)maleic anhydride;479035-70-6;2,5-Furandione, 3,4-bis(bromomethyl)-;SCHEMBL6236482;CHEMBL2270564;DTXSID50423745;AXFDZFNHWXMGNU-UHFFFAOYSA-N

Chemical Property of Bis(bromomethyl)maleic anhydride

Chemical Property:

• PSA: 43.37000
• LogP: 1.15620
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 283.85067
• Heavy Atom Count: 11
• Complexity: 220

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1=C(C(=O)OC1=O)CBr)Br

Technology Process of Bis(bromomethyl)maleic anhydride

There total 1 articles about Bis(bromomethyl)maleic anhydride 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: 62.0%

2,3-Dimethylmaleic anhydride (766-39-2) → 2-(bromomethyl)-3-methyl maleic anhydrate (98453-81-7) + bis(bromomethyl)maleic anhydride (479035-70-6)

Guidance literature:

With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 24h; Heating;

DOI:10.1055/s-2002-31967

Reference yield: 98.0%

bis(bromomethyl)maleic anhydride (479035-70-6) → bis(hydroxymethyl)maleic anhydride (479035-71-7)

Guidance literature:

With potassium hydroxide; at 20 ℃; for 3h;

DOI:10.1055/s-2002-31967

Reference yield:

bis(bromomethyl)maleic anhydride (479035-70-6) → diethyl 3,4-furandicarboxylate (30614-77-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / aq. KOH / 3 h / 20 °C

2: 91 percent / Ph₃P; DEAD / tetrahydrofuran / 3 h / 20 °C

3: 88 percent / H₂SO₄ / 24 h / 20 °C

4: 81 percent / DDQ / dioxane / 24 h / Heating

With potassium hydroxide; sulfuric acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; 2: intramolecular Mitsunobu ring closure;

DOI:10.1055/s-2002-31967

upstream raw materials:

2,3-Dimethylmaleic anhydride

Downstream raw materials:

bis(hydroxymethyl)maleic anhydride

diethyl 3,4-furandicarboxylate