100074-10-0

Basic information

• Product Name: 2-(2,2-dibroMovinyl)furan
• Synonyms: 2-(2,2-dibroMovinyl)furan;2-(2,2-dibromoethenyl)Furan;Furan, 2-(2,2-dibromoethenyl)-
• CAS NO: 100074-10-0
• Molecular Formula: C₆H₄Br₂O
• Molecular Weight: 251.90336
• Mol File: 100074-10-0.mol
• Article Data: 43

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(2,2-dibroMovinyl)furan(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,2-dibroMovinyl)furan(100074-10-0)
• EPA Substance Registry System: 2-(2,2-dibroMovinyl)furan(100074-10-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 100074-10-0(Hazardous Substances Data)

Usage

General Description

2-(2,2-dibromovinyl)furan is a chemical compound with the molecular formula C6H4Br2O. It is a furan derivative with two bromine atoms and a vinyl substituent attached to the furan ring. 2-(2,2-dibroMovinyl)furan is primarily used in organic synthesis and laboratory research as a building block for the preparation of various organic compounds. It is important to handle and store this compound with care, as it is a potentially hazardous chemical that can cause irritation to the eyes, skin, and respiratory system upon exposure. Additionally, it is important to follow proper safety precautions when working with this compound, such as wearing protective clothing and working in a well-ventilated area.

Upstream product

• 98-01-1 furfural 
• 558-13-4 carbon tetrabromide 
• 75-25-2 Bromoform 
• 74-95-3 1,1-dibromomethane 

Downstream Products

• 18649-64-4 2-ethynylfuran 
• 35133-77-8 2-(2-phenylethynyl)furan 
• 1428901-40-9 4-bromo-5-(furan-2-yl)-3-methyl-3-phenyl-3H-pyrazole 
• 1404075-56-4 (E)-1-(furan-2-yl)-5-phenylpent-1-en-3-ol 
• 141632-19-1 (E)-2-(2-(furan-2-yl)vinyl)pyridine 

Relevant articles and documents

1,1-Dibromoalkenes as versatile reagents to a transition metal-free and stereoselective synthesis of (E)-1-bromo-1-selenoalkenes and ketene selenoacetals

We describe here a metal-free and selective method for the synthesis of (E)-1-bromo-1-seleno alkenes and ketene selenoacetals by a stoichiometric and temperature-controlled reaction. These protocols employ a diverse array of 1,1-dibromoalkenes and different diaryl diselenides to afford the corresponding products in good yields and in a short reaction time.

Practical synthesis of (Z)-polyaromatic and heteroaromatic vinylacetylenes

(Chemical Equation Presented) Two synthetic routes to several (Z)-polyaromatic and heteroaromatic substituted vinylacetylenes are described. The nature of aryl- or heteroaryl-substituted carboxaldehyde used as starting material dictated the choice of Wittig salt employed. A very attractive way to construct polyaromatic and pyridine-containing enynes is the reaction of polyaromatic and pyridine-containing aldehydes with bromomethyltriphenylphosphonium bromide in the presence of potassium tert-butoxide followed by a Sonogashira desilylation procedure (method B).

Cyclization of α,ω-diborylalkanes via double Suzuki-Miyaura coupling

Both carbo- and heterocyclic six-membered ring systems (3) containing an exocyclic carbon-carbon double bond have been prepared (25-76%) from α,ω-dienes (1) through the cross coupling of their dihydroboration products (2) with either aromatic or aliphatic vinylidene dibromides (4) in a one-pot Pd-catalyzed sequence.

Synthesis of 1,2-disubstituted acetylenes via copper-catalyzed Suzuki coupling of organoboronic acids with 1,1-dibromo-1-alkenes

An efficient synthesis of 1,2-disubstituted acetylenes has been described. Reactions of organoboronic acids with 1,1-dibromo-1-alkenes in the presence of a catalytic amount of CuI (10 mol %), 8-hydroxyquinoline (10 mol %), and using potassium phosphate as base in C2H5OH afforded the desired 1,2-disubstituted acetylenes in good to excellent yields. It is important to note that the formation of 1,3-diynes, which are derived from the homocoupling of 1,1-dibromo-1-alkenes, can be almost completely suppressed under these optimized conditions.

Nickel-Catalyzed, Regio- and Enantioselective Benzylic Alkenylation of Olefins with Alkenyl Bromide

A NiH-catalyzed migratory hydroalkenylation reaction of olefins with alkenyl bromides has been developed, affording benzylic alkenylation products with high yields and excellent chemoselectivity. The mild conditions of the reaction preclude olefinic products from undergoing further isomerization or subsequent alkenylation. Catalytic enantioselective hydroalkenylation of styrenes was achieved by using a chiral bisoxazoline ligand.

Iron-Catalyzed Reductive Vinylation of Tertiary Alkyl Oxalates with Activated Vinyl Halides

We present herein a rare and efficient method for the creation of vinylated all carbon quaternary centers via Fe-catalyzed cross-electrophile coupling of vinyl halides with tertiary alkyl methyl oxalates. The reaction displays excellent functional group tolerance and broad substrate scope, which allows cascade radical cyclization and vinylation to afford complex bicyclic and spiral structural motifs. The reaction proceeds via tertiary alkyl radicals, and the putative vinyl-Br/Fe complexation appears to be crucial for activating the alkene and enabling a possibly concerted radical addition/C-Fe forming process.