1009-33-2

Basic information

• Product Name: Benzene, 1-chloro-4-(1-cyclopropylethenyl)-
• CAS NO: 1009-33-2
• Molecular Formula: C11H11Cl
• Molecular Weight: 178.661
• Mol File: 1009-33-2.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzene, 1-chloro-4-(1-cyclopropylethenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-chloro-4-(1-cyclopropylethenyl)-(1009-33-2)
• EPA Substance Registry System: Benzene, 1-chloro-4-(1-cyclopropylethenyl)-(1009-33-2)

Safety Data

• Hazardous Substances Data: 1009-33-2(Hazardous Substances Data)

Upstream product

• 6640-25-1 4-chlorophenyl cyclopropyl ketone 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 89619-10-3 1-(1-bromovinyl)-4-chlorobenzene 
• 3002-94-6 cyclopropyllithium 
• 108-90-7 chlorobenzene 
• 765-43-5 Cyclopropyl methyl ketone 
• 106-39-8 bromochlorobenzene 
• 62586-85-0 1-(4-chlorophenyl)-1-cyclopropylethan-1-ol 

Downstream Products

• 119544-80-8 2-cyclopropyl-2-(4-chlorophenyl)ethanol 
• 1234835-99-4 5-(4-chlorophenyl)-1-p-toluenesulfonyl-1,2,3,6-tetrahydropyridine 
• 91398-51-5 4'-chloro-5,6-dihydro-[1,1'-biphenyl]-3(4H)-one 

Relevant articles and documents

Silylium-Ion-Promoted (5+1) Cycloaddition of Aryl-Substituted Vinylcyclopropanes and Hydrosilanes Involving Aryl Migration

A transition-metal-free (5+1) cycloaddition of aryl-substituted vinylcyclopropanes (VCPs) and hydrosilanes to afford silacyclohexanes is reported. Catalytic amounts of the trityl cation initiate the reaction by hydride abstraction from the hydrosilane, and further progress of the reaction is maintained by self-regeneration of the silylium ions. The new reaction involves a [1,2] migration of an aryl group, eventually furnishing 4- rather than 3-aryl-substituted silacyclohexane derivatives as major products. Various control experiments and quantum-chemical calculations support a mechanistic picture where a silylium ion intramolecularly stabilized by a cyclopropane ring can either undergo a kinetically favored concerted [1,2] aryl migration/ring expansion or engage in a cyclopropane-to-cyclopropane rearrangement.

Palladium-catalysed direct cross-coupling of secondary alkyllithium reagents

Palladium-catalysed cross-coupling of secondary C(sp3) organometallic reagents has been a long-standing challenge in organic synthesis, due to the problems associated with undesired isomerisation or the formation of reduction products. Based on our recently developed catalytic C-C bond formation with organolithium reagents, herein we present a Pd-catalysed cross-coupling of secondary alkyllithium reagents with aryl and alkenyl bromides. The reaction proceeds at room temperature and on short timescales with high selectivity and yields. This methodology is also applicable to hindered aryl bromides, which are a major challenge in the field of metal catalysed cross-coupling reactions.

Insecticidal cyclopropyl-substituted di(aryl) compounds

Compounds of the formula STR1 in which Ar is substituted or unsubstituted phenyl, naphthyl, or thienyl; Z is oxygen, sulfur, or methylene; and Ar' is 2-methyl[1,1'-biphenyl]-3-yl, 3-phenoxyphenyl, 4-fluoro-3-phenoxyphenyl, or 6-phenoxy-2-pyridyl exhibit pyrethroid-like insecticidal and acaricidal activity and are relatively harmless to aquatic fauna.