171779-48-9

Basic information

• Product Name: 2-Bromo-5-methyl-5-(4-methylphenyl)-1,6-heptadiene
• Synonyms: 2-Bromo-5-methyl-5-(4-methylphenyl)-1,6-heptadiene
• CAS NO: 171779-48-9
• Molecular Weight: 279.22
• Mol File: 171779-48-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-Bromo-5-methyl-5-(4-methylphenyl)-1,6-heptadiene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-5-methyl-5-(4-methylphenyl)-1,6-heptadiene(171779-48-9)
• EPA Substance Registry System: 2-Bromo-5-methyl-5-(4-methylphenyl)-1,6-heptadiene(171779-48-9)

Safety Data

• Hazardous Substances Data: 171779-48-9(Hazardous Substances Data)

Upstream product

• 2947-61-7 (4-methylphenyl)acetonitrile 
• 171779-51-4 2-Methyl-2-(4-methylphenyl)-5-bromo-5-hexen-1-al 
• 74-95-3 1,1-dibromomethane 
• 75920-45-5 (+/-)-2-(4'-methylphenyl)-propionitrile 

Downstream Products

• 5006-53-1 (+/-)-laurene 
• 5006-53-1 (+/-)-Epilaurene 

Relevant articles and documents

Conformational control in the cyclization of an unsaturated vinyllithium: Synthesis of (±)-laurene

The olefinic vinyllithium 2, derived from 2-bromo-5-methyl-5-(4-methylphenyl)-1,6-heptadiene (3) by low-temperature lithium-bromine exchange, undergoes a diastereoselective 5-exo cyclization at 0°C in the presence of TMEDA to afford the naturally occurring sesquiterpene (±)-laurene (1) in 60% isolated yield along with 17% of the isomeric (±)-epilaurene (4). The diastereoselectivity of the cyclization of 2 is discussed in terms of a transition state for the process that approximates a chair cyclohexane which preferentially adopts a conformation having a pseudoaxial p-tolyl moiety and a pseudoequatorial methyl group at the geminally substituted carbon. In contrast to the behavior of 2, radical-mediated cyclization of 3 proceeds entirely in a 6-endo fashion to give 4-methyl4-(4-methylphenyl)-1-methylenecyclohexane (6) in 93% yield.