3-Bromo-4-(dibromomethyl)-5-hydroxy-2(5H)-furanone

Base Information

• Chemical Name: 3-Bromo-4-(dibromomethyl)-5-hydroxy-2(5H)-furanone
• CAS No.: 132059-53-1
• Molecular Formula: C5H3 Br3 O3
• Molecular Weight: 350.789
• UNII: 0W8WIE8S84
• DSSTox Substance ID: DTXSID9021506
• Nikkaji Number: J647.390C
• Wikidata: Q27237305
• Mol file: 132059-53-1.mol

Synonyms:3-Bromo-4-(dibromomethyl)-5-hydroxy-2(5H)-furanone;132059-53-1;BMX 3;CCRIS 7455;4-bromo-3-(dibromomethyl)-2-hydroxy-2H-furan-5-one;UNII-0W8WIE8S84;3-bromo-4-(dibromomethyl)-5-hydroxyfuran-2(5H)-one;0W8WIE8S84;2(5H)-Furanone, 3-bromo-4-(dibromomethyl)-5-hydroxy-;starbld0007382;SCHEMBL4313769;DTXSID9021506;AKOS030240023;LS-189147;FT-0663692;J-006116;Q27237305

Chemical Property of 3-Bromo-4-(dibromomethyl)-5-hydroxy-2(5H)-furanone

Chemical Property:

• Vapor Pressure: 2.39E-09mmHg at 25°C
• Melting Point: 64-66°C
• Boiling Point: 433.8°Cat760mmHg
• Flash Point: 216.2°C
• PSA: 46.53000
• Density: 2.867g/cm³
• LogP: 1.62650
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 349.76118
• Heavy Atom Count: 11
• Complexity: 223

Purity/Quality:

97% ^*data from raw suppliers

3-Bromo-4-(dibromomethyl)-5-hydroxy-2(5H)-furanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1(C(=C(C(=O)O1)Br)C(Br)Br)O

Technology Process of 3-Bromo-4-(dibromomethyl)-5-hydroxy-2(5H)-furanone

There total 4 articles about 3-Bromo-4-(dibromomethyl)-5-hydroxy-2(5H)-furanone 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: 48.0%

methyl 2,4,4-tribromo-3-(dibromomethyl)but-2-enoate → 3-bromo-4-(dibromomethyl)-5-hydroxy-2(5H)-furanone (132059-53-1)

Guidance literature:

With hydrogen bromide; for 8h; Heating;

DOI:10.1016/S0040-4020(00)00258-1

Reference yield: 32.0%

3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (77439-76-0) → 3-chloro-4-(dibromomethyl)-5-hydroxy-2,5-dihydrofuran-2-one (132059-52-0) + 3-bromo-4-(dibromomethyl)-5-hydroxy-2(5H)-furanone (132059-53-1)

Guidance literature:

With ethyl bromide; sodium bromide; In 1-methyl-pyrrolidin-2-one; at 100 ℃; for 24h;

DOI:10.1081/SCC-120024000

Reference yield:

Methyl 3,3-dimethylacrylate (924-50-5) → 3-bromo-4-(dibromomethyl)-5-hydroxy-2(5H)-furanone (132059-53-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Br₂ / CCl₄ / 1 h / 25 °C

1.2: 77 percent / Et₃N / CH₂Cl₂ / 0 - 25 °C

2.1: 40 percent / NBS / CCl₄ / Irradiation

3.1: 48 percent / conc. HBr (48 percent) / 8 h / Heating

With N-Bromosuccinimide; hydrogen bromide; bromine; In tetrachloromethane; 1.1: Bromination / 1.2: Elimination / 2.1: Bromination / 3.1: Cyclization;

DOI:10.1016/S0040-4020(00)00258-1

upstream raw materials:

3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone

Methyl 3,3-dimethylacrylate

methyl 2-bromo-3-methylbut-2-enoate

Refernces

• 1、 Lloveras, Maia,Ramos, Isabel,Molins, Elies,Messeguer, Angel. "Improved synthesis of three brominated analogues of the potent environmental mutagen 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX)". . p. 3391 - 3397. Retrieved 2007/10/03.