19997-53-6

Basic information

• Product Name: 2-(bromomethyl)-2,3-dihydrobenzofuran
• Synonyms: 2-(bromomethyl)-2,3-dihydrobenzofuran
• CAS NO: 19997-53-6
• Molecular Formula: C₉H₉BrO
• Molecular Weight: 213.07116
• Mol File: 19997-53-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 279 °C at 760 mmHg
• Flash Point: 110.4 °C
• Appearance: /
• Density: 1.481 g/cm³
• Vapor Pressure: 0.00697mmHg at 25°C
• Refractive Index: 1.579
• CAS DataBase Reference: 2-(bromomethyl)-2,3-dihydrobenzofuran(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(bromomethyl)-2,3-dihydrobenzofuran(19997-53-6)
• EPA Substance Registry System: 2-(bromomethyl)-2,3-dihydrobenzofuran(19997-53-6)

Safety Data

• Hazardous Substances Data: 19997-53-6(Hazardous Substances Data)

Usage

General Description

2-(bromomethyl)-2,3-dihydrobenzofuran is a chemical compound that is commonly used in organic synthesis. It is a brominated derivative of 2,3-dihydrobenzofuran, which is a heterocyclic compound that features a furan ring fused to a benzene ring. The bromomethyl group in the compound makes it useful for various chemical reactions, including nucleophilic substitution and palladium-catalyzed coupling reactions. 2-(bromomethyl)-2,3-dihydrobenzofuran has been studied for its potential pharmaceutical applications, including as a precursor for the synthesis of biologically active molecules. Additionally, it is also used as a building block for the synthesis of various organic compounds in the pharmaceutical, agrochemical, and material science industries.

InChI:InChI=1/C9H9BrO/c10-6-8-5-7-3-1-2-4-9(7)11-8/h1-4,8H,5-6H2

Upstream product

• 84767-97-5 2-(2,3-dibromopropyl)phenyl acetate 
• 69914-63-2 2-chloromercurymethyl-2,3-dihydrobenzofuran 
• 1745-81-9 o-Allylphenol 
• 51496-94-7 1-allyl-2-(benzyloxy)benzene 
• 84767-98-6 2-allylphenol dibromide 
• 4125-54-6 2-allylphenyl acetate 
• 3698-28-0 2-allylanisole 

Relevant articles and documents

Synthesis of monofluorinated C4-building blocks based on methallyl chloride

Halofluorination of methallyl chloride using N-halosuccinimides in combination with triethylamine trishydrofluoride (Et3N*3HF) gave in each case more than 98percent of the Markovnikov products and 2percent of the regioisomers in good yield.The formal addition of methanesulfenyl fluoride with the combination of dimethyl(methylthio)sulfonium fluoroborate (DMTSF) and Et3N*3HF gave a 94:6 mixture of both regioisomers.Only small phenylsulfenyl fluorination of methallyl chloride has been observed when treated with N-phenylthiophthalimide (NPTP) and Olah's reagent.With benzenesulfenyl chloride, 1,3-dichloro-2-methyl-2-(phenylthio)propane is formed which on treatment with Olah's reagent at 0 deg C or with Et3N*3HF at 60 deg C rearranges to 1,2-dichloro-2-methyl-3-(phenylthio)propane.Treatment of 1,3-dichloro-2-methyl-2-(phenylthio)propane with silver fluoride in methylene chloride at -30 deg C gave 1-chloro-2-fluoro-2-methyl-3-(phenylthio)propane which was also obtained by reaction of 1-bromo-3-chloro-2-fluoro-2-methylpropane with thiophenolate.Chlorofluorination of methallylphenylthio ether using NCS/Et3N*3HF failed, while corresponding reactions with NBS or NIS and Et3N*3HF gave mainly the bromo- or iodo-fluorides with Markovnikov orientation in 61percent or 35percent yields.Related halofluorinations of methallylphenyl ether gave the halofluorides in good yield.All attempts to obtain chromanes or thiochromanes bearing a 3-fluorine substituent by cyclization of these halofluorinated ethers or thio ethers failed using different Lewis acids.However, the benzyl protected o-allylphenol which was bromofluorinated with NBS/Et3N*3HF in good yield gave on catalytic hydrogenation over Pd/C the 3-fluoro-2H-chromane in nearly quantitative yield. - Keywords: Electrophilic addition; Halofluorination; Sulfenylfluorination; N-Halosuccinimides; Dimethyl(methylthio)sulfonium tetrafluoroborate; Triethylamine trishydrofluoride

The purity of bromomethylcoumaran according to the method of

-