3727-48-8

Basic information

• Product Name: 1,3-Cyclohexadiene,2-bromo-(7CI,8CI,9CI)
• Synonyms: 1,3-Cyclohexadiene,2-bromo-(7CI,8CI,9CI)
• CAS NO: 3727-48-8
• Molecular Formula: C₆H₇Br
• Molecular Weight: 159.02378
• Product Categories: HALIDE
• Mol File: 3727-48-8.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3-Cyclohexadiene,2-bromo-(7CI,8CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Cyclohexadiene,2-bromo-(7CI,8CI,9CI)(3727-48-8)
• EPA Substance Registry System: 1,3-Cyclohexadiene,2-bromo-(7CI,8CI,9CI)(3727-48-8)

Safety Data

• Hazardous Substances Data: 3727-48-8(Hazardous Substances Data)

Usage

Structure

Substituted cyclohexadiene derivative with a bromine atom attached to the second carbon of the cyclohexadiene ring

Applications

a. Organic synthesis
b. Building block in the synthesis of more complex organic compounds
c. Intermediate in the pharmaceutical and agrochemical industries
d. Potential applications in material science
e. Reagent in chemical research

Chemical reactions

Can undergo substitution, addition, and elimination reactions

Safety

Handle with care due to potential hazards if not properly managed

Upstream product

• 17202-32-3 1,6-dibromocyclohex-1-ene 
• 14310-04-4 2-bromocyclohex-2-en-1-yl acetate 
• 109380-07-6 2-bromocyclohex-2-en-1-ol 
• 2568-36-7 6,6-dibromobicylo[3.1.0]hexane 
• 97861-71-7 2-bromo-2-cyclohexenyl diethyl phosphate 
• 97861-66-0 ethyl 2-bromo-2-cyclohexenyl carbonate 

Downstream Products

• 211503-84-3 2-chloro-5-(1,5-cyclohexadienyl)pyridine 
• 1233405-12-3 (E)-2-(2-(tert-butyldimethylsilyloxy)-5,5-dimethylcyclohexylidene)-1-(cyclohexa-1,5-dienyl)ethanone 
• 211503-87-6 (1S,4R)-5-(6-Chloro-pyridin-3-yl)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester 
• 211503-90-1 (1S,4R,5R)-5-(6-Chloro-pyridin-3-yl)-2-oxa-3-aza-bicyclo[2.2.2]octane-3-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester 
• 211503-92-3 N-[(1R,2R,4R)-4-bromo-2-(6-chloro(3-pyridyl))cyclohexyl](tert-butoxy)carboxamide 
• 211503-91-2 (-)-tert-butyl N-[(1R,2R,4S)-2-(6-chloropyridin-3-yl)-4-hydroxycyclohexyl]carbamate 
• 217323-82-5 (1R,2R,4R)-4-bromo-2-(6-chloropyridin-3-yl)cyclohexanamine 
• 140111-52-0 epibatidine 
• 84099-61-6 1,5-Cyclohexadiene-1-carboxaldehyde 
• 84099-68-3 1-(1,3-cyclohexadiene-2-yl)-1-methoxy-1-cyclopropylmethanol 

Relevant articles and documents

Simple and efficient synthesis of bromine-substituted 1,3-dienes and 1,3,5-cycloheptatriene by vacuum pyrolysis of gem-dibromocyclopropanes

To establish whether the results obtained by the gas phase pyrolysis of 6,6-dihalobicyclo[3.1.0]hexanes by HeI photoelectron spectroscopy using a high power CW CO2 laser as a directed heat source can be achieved on a preparatory scale using a modified apparatus, we carried out the gas phase pyrolysis of a few representative gem-dibromocyclopropanes such as 1,1-dibromo-2,2,3,3-tetramethylcyclopropane (1), 1,1-dibromo-2,2-dimethyl-cyclopropane (2), 1,1-dibromo-cis-2,3-dimethylcyclopropane (3), 1,1-dibromo-trans-2,3-dimethylcyclopropane (4), 6,6-dibromobicyclo[3.1.0]hexane (5) and 7,7-dibromobicyclo[4.1.0]heptane (6). Except 7,7-dibromobicyclo[4.1.0]heptane, that gave 1,3,5-cycloheptatriene in 72% yield at 525°C, 1, 2, 3, 4 and 5 readily lose HBr at 400-560°C in the gas phase to produce β-bromo-1,3-dienes in high chemical yields and purity. The dienes are potentially useful starting substrates for the Diels-Alder reactions.

A NEW TYPE OF FUNCTIONAL GROUP DIFFERENTIATION IN PALLADIUM-CATALYZED REACTIONS

Products of palladium-catalyzed ethynylations of various 2-bromoallyl acetates show that the formation of ?-vinylpalladium intermediates, instead of ?-allylpalladium complexes, is preferred in such substrates.