65001-55-0

Basic information

• Product Name: Benzene, 2-(2-butenyl)-1,3,5-trimethyl-, (E)-
• CAS NO: 65001-55-0
• Molecular Formula: C13H18
• Molecular Weight: 174.286
• Mol File: 65001-55-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Benzene, 2-(2-butenyl)-1,3,5-trimethyl-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 2-(2-butenyl)-1,3,5-trimethyl-, (E)-(65001-55-0)
• EPA Substance Registry System: Benzene, 2-(2-butenyl)-1,3,5-trimethyl-, (E)-(65001-55-0)

Safety Data

• Hazardous Substances Data: 65001-55-0(Hazardous Substances Data)

Upstream product

• 4784-77-4 (E/Z)-crotyl bromide 
• 5980-97-2 mesitylboronic acid 
• 56535-63-8 (E)-4-bromopent-2-ene 
• 2633-66-1 2-mesitylmagnesium bromide 
• 576-83-0 2,4,6-trimethylphenyl bromide 
• 65001-62-9 3-buten-2-yl benzoate 
• 76454-93-8 (E)-2-butenyl 4-methylbenzenesulfonate 
• 108-67-8 1,3,5-trimethyl-benzene 

Relevant articles and documents

Gold-catalyzed allylation of aryl boronic acids: Accessing cross-coupling reactivity with gold

A sp3-sp2 C?C cross-coupling reaction catalyzed by gold in the absence of a sacrificial oxidant is described. Vital to the success of this method is the implementation of a bimetallic catalyst bearing a bis(phosphino)amine ligand. A mechanistic hypothesis is presented, and observable transmetalation, C?Br oxidative addition, and C?C reductive elimination in a model gold complex are shown. We expect that this method will serve as a platform for the development of novel transformations involving redox-active gold catalysts.

Conjugative interaction in styrenes

Conjugative interactions of the carbon-carbon double bond are fundamental in organic chemistry. In this work, equilibria are established among conjugated and unconjugated isomers of two β-substituted styrenes, 1-phenylbut-1-ene and 1-phenyl-3-methylbut-1-ene, and one α,β-disubstituted styrene, 2-phenyl-5-methylhex-2-ene, over a range of temperatures (the van't Hoff method) in hexamethylphosphoric triamide and potassium tert-butoxide. From the trans styrenes of the first two sets, an enthalpy of conjugative interaction of phenyl vis-a-vis alkyl (ΔΔH(ConjInter/Alk)) = -2.5 ± 0.2 kcal/mol [-5.1 kcal/mol defined as phenyl vis-a-vis hydrogen (ΔΔH(ConjInter/H))] is observed, while the cis styrenes reveal an attenuated ΔΔH(ConjInter/Alk) of -1.1 kcal/mol (ΔΔH(ConjInter/H)) = -2.7 kcal/ mol). The α-methyl group in the third set also leads to a reduced conjugative interaction. Entropy plays an important role in determining positions of equilibrium. Free energies of conjugation are reported for several sterically hindered o-methyl-substituted styrenes.