4437-18-7

Basic information

• Product Name: 2-(Bromomethyl)furan
• Synonyms: 2-(Bromomethyl)furan;2-Furylmethyl bromide;Furfuryl bromide;Furan, 2-(bromomethyl)-
• CAS NO: 4437-18-7
• Molecular Formula: C₅H₅BrO
• Molecular Weight: 161
• Product Categories: Furans
• Mol File: 4437-18-7.mol
• Article Data: 34

Chemical Properties

• Boiling Point: 155 °C
• Flash Point: 47 °C
• Appearance: /
• Density: 1.582
• Vapor Pressure: 4.01mmHg at 25°C
• Refractive Index: 1.5380 (estimate)
• CAS DataBase Reference: 2-(Bromomethyl)furan(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Bromomethyl)furan(4437-18-7)
• EPA Substance Registry System: 2-(Bromomethyl)furan(4437-18-7)

Safety Data

• Hazardous Substances Data: 4437-18-7(Hazardous Substances Data)

Usage

General Description

2-(Bromomethyl)furan is a chemical compound with the molecular formula C5H5BrO. It is a colorless to pale yellow liquid with a pungent odor, and it is primarily used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. 2-(Bromomethyl)furan is also used as a reagent in organic chemistry reactions and as a building block for the synthesis of other organic compounds. This chemical is considered to be harmful if ingested, inhaled, or absorbed through the skin, and caution should be exercised when handling it. Additionally, it is important to store and dispose of 2-(Bromomethyl)furan properly to prevent environmental contamination.

InChI:InChI=1/C5H5BrO/c6-4-5-2-1-3-7-5/h1-3H,4H2

Upstream product

• 534-22-5 2-methylfuran 
• 98-01-1 furfural 
• 92785-12-1 Co(ONC(CH₃)C(CH₃)NOH)2(pyridine)(furfuryl) 
• 7726-95-6 bromine 
• 98-00-0 (2-furyl)methyl alcohol 
• 558-13-4 carbon tetrabromide 
• 164513-47-7 3-bromo-2-bromomethylfuran 
• 594-19-4 tert.-butyl lithium 
• 108-18-9 diisopropylamine 
• 7440-44-0 pyrographite 
• 17389-69-4 ethyl-furfuryl-methyl-amine 
• 60-29-7 diethyl ether 
• 506-68-3 bromocyane 
• 81404-55-9 N-methyl,N-benzyl furfurylamine 

Downstream Products

• 190840-82-5 bis(furan-2-ylmethyl)(4-methoxyphenyl)amine 
• 105918-53-4 2-amino-3-furfuryloxybenzoic acid 
• 76836-67-4 3-<2-(2-Furylmethoxy)phenyl>-2-phenyl-2-oxirancarbonitril 
• 76836-70-9 1-<2-(3-Cyan-3-phenyl-2-oxiranyl)phenoxymethyl>-7-oxabicyclo<2.2.1>hept-2-en-2,3-dicarbonsaeure-dimethylester 
• 76836-68-5 1-<2-(3-Cyan-3-phenyl-2-oxiranyl)phenoxymethyl>-7-oxabicyclo<2.2.1>hepta-2,5-dien-2,3-dicarbonsaeure-dimethylester 
• 114325-68-7 1,4-dihydro-1,4-epoxynaphthalen-1-ylmethyl o-bromophenyl ether 
• 18240-50-1 bis((furan-2-yl)methyl)amine 
• 617-89-0 furan-2-ylmethanamine 
• 103642-16-6 1-[2-(4-chloro-benzhydryloxy)-ethyl]-4-furfuryl-piperazine 
• 116436-17-0 trifurfuryl-amine 
• 685898-83-3 2-[β-(m-methoxyphenyl)ethyl]furan 
• 98-00-0 (2-furyl)methyl alcohol 
• 76836-66-3 o-(2-furylmethyloxy)benzaldehyde 

Relevant articles and documents

Preparation and root growth-modulatory activity of N-substituted 2-acetylamino-2-ethoxycarbonyl-3-(2-furyl)propanamides

N-Substituted 2-acetylamino-2-ethoxycarbonyl-3-(2-furyl)propanamides (8) were synthesized through the reaction of amines (13) with 2-acetylamino-2-ethoxycarbonyl-3-(2-furyl)propanoic acid (3b), which was prepared via condensation of 2-(bromomethyl)furan (10b) with diethyl acetamidomalonate, followed by partial hydrolysis of the resultant diethyl ester (3a) in the presence of barium hydroxide. However, bulky amines such as tert-butyl-amine of 2-trifluoromethylaniline did not afford the corresponding diamides (8). The biological activity of the prepared diamides (8) as root growth modulators was examined by germination assay using rape and leek seeds. N-(5-Bromo-2-thiazolyl)- and N-(4-chloro-2-benzothiazolyl)-2-acetylamino-2-ethoxycarbonyl-3-(2-furyl) propanamides (8h, i) both potently inhibited the root growth of rape seedlings, but were less effective in the case of leek seeds. The herbicide 2,4-dichlorophenoxyacetic acid completely inhibited root growth in both cases.

[1,3]-Claisen rearrangement via removable functional group mediated radical stabilization

A thermal O-to-C [1,3]-rearrangement of α-hydroxy acid derived enol ethers was achieved under mild conditions. The 2-aminothiophenol protection of carboxylic acids facilitates formation of the [1,3] precursor and its thermal rearrangement via stabilization of a radical intermediate. Experimental and theoretical evidence for dissociative radical pair formation, its captodative stability via aminothiophenol, and a unique solvent effect are presented. The aminothiophenol was deprotected from rearrangement products as well as after derivatization to useful synthons.

Visible-Light-Induced Intermolecular Dearomative Cyclization of Furans: Synthesis of 1-Oxaspiro[4.4]nona-3,6-dien-2-one

A fac-Ir(ppy)3-catalyzed intermolecular dearomative cyclization of 2-bromo-2-((5-bromofuran-2-yl)methyl)malonate and alkynes affording substituted spirolactones in yields of 19-91% via a 5-exo-dig radical cyclization under visible light is presented. This method provides a new access to the synthesis of spirocycle skeletons applying water as an external oxygen source under mild reaction conditions.