4-Bromo-3-(bromomethyl)but-2-enoic acid

Base Information

• Chemical Name: 4-Bromo-3-(bromomethyl)but-2-enoic acid
• CAS No.: 75887-43-3
• Molecular Formula: C5H6Br2O2
• Molecular Weight: 257.909
• NSC Number: 126830
• DSSTox Substance ID: DTXSID30298897
• Mol file: 75887-43-3.mol

Synonyms:4-bromo-3-(bromomethyl)but-2-enoic acid;75887-43-3;NSC126830;DTXSID30298897;NSC-126830

Chemical Property of 4-Bromo-3-(bromomethyl)but-2-enoic acid

Chemical Property:

• Vapor Pressure: 5.82E-06mmHg at 25°C
• Boiling Point: 353.9°Cat760mmHg
• Flash Point: 167.9°C
• Density: 2.055g/cm³
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 257.87141
• Heavy Atom Count: 9
• Complexity: 125

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C(=CC(=O)O)CBr)Br

Technology Process of 4-Bromo-3-(bromomethyl)but-2-enoic acid

There total 2 articles about 4-Bromo-3-(bromomethyl)but-2-enoic acid 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: 95.0%

3-Methylbutenoic acid (541-47-9) → 4-bromo-3-(bromomethyl)but-2-enoic acid (75887-43-3)

Guidance literature:

With N-Bromosuccinimide; Perbenzoic acid; In tetrachloromethane; for 4h; Heating;

DOI:10.1016/0040-4020(96)00705-3

Reference yield:

3-Methylbutenoic acid (541-47-9) + dibenzoyl peroxide (94-36-0) → 4-bromo-3-(bromomethyl)but-2-enoic acid (75887-43-3)

Guidance literature:

3-Methylbutenoic acid; With N-Bromosuccinimide; In tetrachloromethane; at 60 ℃; for 3h;

dibenzoyl peroxide; In tetrachloromethane; at 60 ℃; for 6h;

DOI:10.1039/c3cc40757h

Reference yield:

4-bromo-3-(bromomethyl)but-2-enoic acid (75887-43-3) → dihydro-4-methyl-2(3H)-furanone (64190-48-3,65284-00-6,70470-05-2,1679-49-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / water / 20 °C

2: palladium on activated charcoal; hydrogen / methanol / 20 °C

With palladium on activated charcoal; hydrogen; sodium hydroxide; In methanol; water;

DOI:10.1002/ejoc.201402218

upstream raw materials:

3-Methylbutenoic acid

dibenzoyl peroxide

Downstream raw materials:

3-bromomethyl-2-butenolide

4-Methyl-5-[(2E,4E)-3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dien-(E)-ylidene]-5H-furan-2-one

(5Z,2'E,4'E)-4-methyl-5-[3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienylidene]-(5H)-furan-2-one

(+/-)-marasmic acid