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

Description

2-(Bromomethyl)furan, with the molecular formula C5H5BrO, is a colorless to pale yellow liquid characterized by a pungent odor. It is a versatile chemical intermediate that plays a significant role in the synthesis of pharmaceuticals and agrochemicals. Additionally, it serves as a reagent in organic chemistry reactions and a building block for the creation of other organic compounds. Due to its potential harmful effects if ingested, inhaled, or absorbed through the skin, careful handling and proper storage and disposal are essential to prevent environmental contamination.

Uses

Used in Pharmaceutical Industry:
2-(Bromomethyl)furan is used as a chemical intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and medications. Its unique structure allows for the creation of a wide range of compounds with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 2-(Bromomethyl)furan serves as an intermediate in the production of pesticides and other crop protection agents. Its involvement in the synthesis of these chemicals helps to enhance crop yields and protect plants from pests and diseases.
Used as a Reagent in Organic Chemistry:
2-(Bromomethyl)furan is utilized as a reagent in various organic chemistry reactions, facilitating the formation of new compounds and aiding in the advancement of chemical research and development.
Used as a Building Block for Organic Compounds:
This chemical compound also acts as a building block for the synthesis of other organic compounds, enabling the creation of a diverse array of molecules with different properties and applications across various industries.

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

Upstream product

• 164513-47-7 3-bromo-2-bromomethylfuran 
• 594-19-4 tert.-butyl lithium 
• 108-18-9 diisopropylamine 
• 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 
• 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 
• 534-22-5 2-methylfuran 

Downstream Products

• 190840-82-5 bis(furan-2-ylmethyl)(4-methoxyphenyl)amine 
• 190840-84-7 bis(furan-2-ylmethyl)(4-methoxybenzyl)amine 
• 190840-83-6 N-benzyl-1-(furan-2-yl)-N-(furan-2-ylmethyl)methanamine 
• 4066-39-1 (rac)-2-amino-3-furan-2-yl-propionic acid 
• 4066-17-5 amino-furfuryl-malonic acid 
• 591769-65-2 2-(4-phenylsulfonylbut-2-ynyloxymethyl)furan 
• 591769-64-1 2-(4-phenylsulfanylbut-2-ynyloxymethyl)furan 
• 959402-69-8 C₂₆H₂₅N₃O₆S 
• 43091-00-5 2-[(phenylsulfonyl)methyl]furan 
• 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 

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.