10178-57-1

Basic information

• Product Name: 7-broMo-2,2-diMethyl-2,3-dihydro-1-benzofuran
• Synonyms: 7-broMo-2,2-diMethyl-2,3-dihydro-1-benzofuran;7-bromo-2,2-dimethyl-2,3-dihydrobenzofuran
• CAS NO: 10178-57-1
• Molecular Formula: C10H11BrO
• Molecular Weight: 227.09774
• Mol File: 10178-57-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 261°C at 760 mmHg
• Flash Point: 103.4°C
• Appearance: /
• Density: 1.383g/cm³
• Vapor Pressure: 0.0192mmHg at 25°C
• Refractive Index: 1.551
• CAS DataBase Reference: 7-broMo-2,2-diMethyl-2,3-dihydro-1-benzofuran(CAS DataBase Reference)
• NIST Chemistry Reference: 7-broMo-2,2-diMethyl-2,3-dihydro-1-benzofuran(10178-57-1)
• EPA Substance Registry System: 7-broMo-2,2-diMethyl-2,3-dihydro-1-benzofuran(10178-57-1)

Safety Data

• Hazardous Substances Data: 10178-57-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 34, p. 6939, 1993 DOI: 10.1016/S0040-4039(00)91836-7

InChI:InChI=1/C10H11BrO/c1-10(2)6-7-4-3-5-8(11)9(7)12-10/h3-5H,6H2,1-2H3

Upstream product

• 153529-64-7 7-(2'-hydroxy-2'-methylpropyl)-1H-benzotriazol-1-amine 
• 308110-31-8 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl trifluoromethasulfonate 
• 68298-46-4 2,3-dihydro-2,2-dimethyl-7-aminobenzofuran 
• 153529-55-6 [7-(2-Hydroxy-2-methyl-propyl)-benzotriazol-1-yl]-carbamic acid tert-butyl ester 

Relevant articles and documents

A New Approach to Dihydrobenzofurans by Intramolecular Trapping of Benzynes by Hydroxyl Functions

The adducts 3, derived from condensations of the 1-aminobenzotriazole dianion 2 and aldehydes or ketones, are converted into the corresponding benzynes upon exposure to either N-bromosuccinimide or lead(IV) acetate; intramolecular trapping by the hydroxyl group then leads to the dihydrobenzofurans 4, 7, 8 and 9 in 38-75percent isolated yields.

A new approach to dihydrobenzofurans and dihydrobenzopyrans (chromans) based on the intramolecular trapping by alcohols of benzynes generated from 7-substituted-1-aminobenzotriazoles

1-Aminobenzotriazoles 9 having 7-hydroxyalkyl substituents are efficiently convened into the corresponding benzynes 4 when treated with N- iodosuccinimide which then undergo highly efficient intramolecular trapping by the pendant hydroxyl groups leading to dihydrobenzofurans 24-26 and dihydrobenzopyrans (chromans) 27, with incorporation of a synthetically useful iodine atom adjacent to the new ether bond, which allows subsequent and high-yielding homologations using Stille, Sonogashira and Heck couplings. (C) 2000 Elsevier Science Ltd.