99660-97-6

Basic information

• Product Name: 3,5-DIBROMOBENZO[B]FURAN
• Synonyms: 3,5-DIBROMOBENZO[B]FURAN;3,5-DIBROMO-1-BENZOFURAN;3,5-Dibromobenzo[b]furane;3,5-Dibromobenzofuran
• CAS NO: 99660-97-6
• Molecular Formula: C₈H₄Br₂O
• Molecular Weight: 275.92
• Product Categories: Furans, Benzofurans & Dihydrobenzofurans;Halides;Furans, Benzofurans & Dihydrobenzofurans
• Mol File: 99660-97-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 77 °C
• Boiling Point: 294.852 °C at 760 mmHg
• Flash Point: 132.122 °C
• Appearance: /
• Density: 1.989 g/cm³
• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.669
• Storage Temp.: Refrigerated.
• CAS DataBase Reference: 3,5-DIBROMOBENZO[B]FURAN(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIBROMOBENZO[B]FURAN(99660-97-6)
• EPA Substance Registry System: 3,5-DIBROMOBENZO[B]FURAN(99660-97-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 22-26-36/37/39
• Hazardous Substances Data: 99660-97-6(Hazardous Substances Data)

Usage

General Description

3,5-Dibromobenzo[b]furan is a chemical compound with the molecular formula C8H4Br2O. It is a heterocyclic aromatic compound, which means it contains a ring structure with alternating carbon and oxygen atoms. The presence of two bromine atoms in the molecule makes it highly reactive and it is commonly used in organic synthesis as a building block for the preparation of various pharmaceuticals and agrochemicals. It has also been studied for its potential as a flame retardant due to its high thermal stability. Additionally, 3,5-dibromobenzo[b]furan has been found to exhibit moderate to high antimicrobial and antifungal activities, making it a potentially valuable compound for medicinal and agricultural applications.

InChI:InChI=1/C8H4Br2O/c9-5-1-2-8-6(3-5)7(10)4-11-8/h1-4H

Upstream product

• 568593-05-5 2,3,5-tribromo-2,3-dihydrobenzofuran 
• 23145-07-5 5-bromobenzofuran 
• 64150-67-0 2,3,5-tribromobenzofuran 

Downstream Products

• 99661-09-3 benzoyl-2 dibromo-3,5 benzofuranne 
• 99661-14-0 anisoyl-2 dibromo-3,5 benzofuranne 
• 489422-91-5 tert-butyl[4-(3,5-dibromobenzo[b]furan-2-yl)-2-methoxyphenoxy]dimethylsilane 
• 489423-02-1 (E)-tert-butyl{2-methoxy-4-[3-methyl-5-(prop-1-enyl)benzo[b]furan-2-yl]phenoxy}dimethylsilane 
• 489423-03-2 (E)-tert-butyldimethyl{4-[3-methyl-5-(prop-1-enyl)benzo[b]furan-2-yl]phenoxy}silane 
• 489422-89-1 3,5-dibromo-2-(3,4-dimethoxyphenyl)benzo[b]furan 
• 365448-15-3 tert-butyl[4-(3,5-dibromobenzo[b]furan-2-yl)phenoxy]dimethylsilane 
• 365448-05-1 3,5-dibromo-2-(4-methoxyphenyl)benzo[b]furan 
• 365448-06-2 5-bromo-2-(4-methoxyphenyl)-3-methylbenzo[b]furan 
• 41744-29-0 (E)-2-(3,4-dimethoxyphenyl)-3-methyl-5-(prop-1-enyl)benzo[b]furan 
• 41744-28-9 eupomatenoid-5 
• 40341-58-0 (E)-2-(4-methoxyphenyl)-3-methyl-5-(prop-1-enyl)benzo[b]furan 

Relevant articles and documents

NaBH4-TMEDA and a palladium catalyst as efficient regio- and chemoselective system for the hydrodehalogenation of halogenated heterocycles

The pair NaBH4-TMEDA as hydride source and a palladium catalyst in THF prove to be an efficient system for the hydrodehalogenation of halogenated heterocycles with one or more heteroatoms. In general, Pd(OAc) 2-PPh3 rapidly hydrodehalogenates reactive halo-heterocycles such as bromo-pyridines, -quinolines, -thiophenes, -indoles, -imidazoles, etc., at room temperature in very good yields, whereas in most cases PdCl2(dppf) reduces less reactive halides such as chloro-pyridines, -quinolines, -pyrimidines and bromo-indoles, -benzofurans, etc. Moreover, PdCl2(tbpf) shows to be even more active removing the 2- and 5-chlorine from both thiophene and thiazole rings. The reaction conditions tolerate various functional groups, allowing highly chemoselective reactions in the presence of halide, ester, alkyne, alkene and nitrile substituents. Moreover, with a proper selection of the catalyst it is also possible to obtain a good control in the regioselective hydrodehalogenation of a variety of polyhalogenated substrates.

Regioselective C-C bond formation reactions on 2,3-dibromo- and 2,3,5-tribromobenzofuran as an access to multiply substituted benzofurans. Total syntheses of eupomatenoids 3, 4, 5, 6, and 15

Regioselective C-C-bond formation reactions at 2,3-dibromobenzofuran (1) and 2,3,5-tribromobenzofuran (6) were studied. Pd-catalyzed Sonogashira and Negishi cross-coupling occurred with perfect regioselectivity at carbon atom C-2 to provide 2-substituted 3-bromobenzofurans (12, 14) and 3,5-dibromobenzofurans (17, 18) in 50-91% yield. A regioselective displacement of the bromine substituents in 3,5-dibromobenzofurans 18 was achieved by a halogen-metal exchange reaction at carbon atom C-3 and by a Nicatalyzed Kumada cross-coupling at C-5. The methodology was applied to the synthesis of eupomatenoids 3, 4, 5, 6, and 15 (5). The synthesis of these compounds was achieved in overall yields of up to 60%.