13271-49-3

Basic information

• Product Name: 5,5-Dimethyl-3-bromocyclohex-2-enone
• Synonyms: 5,5-Dimethyl-3-bromocyclohex-2-enone;3-bromo-5,5-dimethylcyclohex-2-enone
• CAS NO: 13271-49-3
• Molecular Formula: C₈H₁₁BrO
• Molecular Weight: 203.08
• Mol File: 13271-49-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 222.2°Cat760mmHg
• Flash Point: 53.7°C
• Appearance: /
• Density: 1.381g/cm³
• Vapor Pressure: 0.103mmHg at 25°C
• Refractive Index: 1.517
• CAS DataBase Reference: 5,5-Dimethyl-3-bromocyclohex-2-enone(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5-Dimethyl-3-bromocyclohex-2-enone(13271-49-3)
• EPA Substance Registry System: 5,5-Dimethyl-3-bromocyclohex-2-enone(13271-49-3)

Safety Data

• Hazardous Substances Data: 13271-49-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H11BrO/c1-8(2)4-6(9)3-7(10)5-8/h3H,4-5H2,1-2H3

Upstream product

• 4694-17-1 5,5-dimethlycyclohex-2-en-1-one 
• 17530-69-7 3-chloro-5,5-dimethylcyclohex-2-en-1-one 
• 67-66-3 chloroform 
• 1195-91-1 2-bromodimedone 
• 7789-60-8 phosphorus tribromide 
• 18922-00-4 5,5-dimethyl-3-oxocyclohex-1-en-1-yl methanesulfonate 
• 3471-13-4 dimedone 
• 126-81-8 dimedone 

Downstream Products

• 56745-22-3 3-butyl-5,5-dimethylcyclohex-2-en-1-one 
• 117582-48-6 3-(10-Cyanodecanyl)-5,5-dimethyl-2-cyclohexenone 
• 76399-19-4 (E)-3-bromo-5,5-dimethyl-2-cyclohexenylidene acetonitrile 
• 76399-18-3 (Z)-3-bromo-5,5-dimethyl-2-cyclohexenylidene acetonitrile 
• 52735-51-0 5,5-dimethyl-3-(phenylthio)cyclohex-2-enone 
• 14376-79-5 3,3,5,5-tetramethylcyclohexanone 
• 408314-23-8 2,3-dibrom-5,5-dimethylcyclohex-2-en-1-on 
• 1202794-02-2 (R)-3-(3-tert-butoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)-5,5-dimethylcyclohex-2-enone 
• 608533-53-5 methyl (E)-2-(5,5-dimethyl-3-oxo-cyclohex-1-enyl)-3-phenyl-acrylate 
• 608533-24-0 methyl (Z)-2-(5,5-dimethyl-3-oxo-cyclohex-1-enyl)-3-phenyl-acrylate 
• 96530-11-9 VIa-p-nitrobenzoate 
• 96530-07-3 5,5-dimethyl-3-phenoxy-2-cyclohexenol 
• 77670-23-6 5,5-Dimethyl-3-(phenylthio)cyclohexanone 
• 96530-10-8 5,5-dimethyl-3-phenylthiocyclohexanol 

Relevant articles and documents

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Tandem Ullmann-Goldberg Cross-Coupling/Cyclopalladation-Reductive Elimination Reactions and Related Sequences Leading to Polyfunctionalized Benzofurans, Indoles, and Phthalanes

On exposure to a combination of Cu[I]- and Pd[0]-based catalysts, compounds such as 1 and 7 engage in tandem Ullmann-Goldberg cross-coupling and cyclopalladation-reductive elimination reactions to give benzofurans such as 8. Related reactions involving hetero-Michael additions of o-halogenated phenols or anilines to propiolates and the Pd[0]-catalyzed cyclization of the resulting conjugates provide, in a one-pot process, alternately functionalized benzofurans, indoles, or phthalanes.

Design, synthesis, and diversification of 3,5-substituted enone library

This paper describes the synthesis of a 300 member library of 3,5-substituted enones. The synthesis starts with 6 different bromoenones that are accessed from the corresponding 1,3 diones. These bromides are then diversified by Suzuki coupling with a variety of aromatic and vinyl boronic acids. Additionally a small series of triazoles was synthesized by a Sonogashira coupling reaction dipolar cycloaddition sequence. The library was analyzed by principal component analysis to examine its diversity.

VILSMEIER REAGENTS: PREPARATION OF β-HALO-α,β-UNSATURATED KETONES

A new method for the preparation of β-chloro and β-bromo-α,β-unsaturated ketones from β-diketones is described.Utilizing Vilsmeier reagents (prepared from N,N-dimethylformamide and oxalyl chloride or oxalyl bromide) β-halo-α,β-unsaturated ketones are isolated in excellent yields.