133302-95-1

Basic information

• Product Name: Cyclopentene, 1-bromo-2-methyl- (9CI)
• Synonyms: Cyclopentene, 1-bromo-2-methyl- (9CI)
• CAS NO: 133302-95-1
• Molecular Formula: C₆H₉Br
• Molecular Weight: 161.03966
• Product Categories: HALIDE
• Mol File: 133302-95-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cyclopentene, 1-bromo-2-methyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopentene, 1-bromo-2-methyl- (9CI)(133302-95-1)
• EPA Substance Registry System: Cyclopentene, 1-bromo-2-methyl- (9CI)(133302-95-1)

Safety Data

• Hazardous Substances Data: 133302-95-1(Hazardous Substances Data)

Upstream product

• 75-89-8 2,2,2-trifluoroethanol 
• 57155-01-8 1-Cyclobutylideneethyl triflate 
• 75415-78-0 1,2-dibromocyclopentene 
• 74-88-4 methyl iodide 
• 3168-90-9 1-(2-methylcyclopent-1-enyl)ethanone 
• 67209-77-2 2-methyl-cyclopent-1-enecarboxylic acid 
• 59253-86-0 2-methyl-1-cyclopentenecarbonyl chloride 
• 176980-06-6 2-Methyl-cyclopent-1-enecarboxylic acid 4-methyl-2-thioxo-thiazol-3-yl ester 

Downstream Products

• 1356829-82-7 (3aR,6aR)-6a-methyl-3-phenyl-4,5,6,6a-tetrahydropentalen-1(3aH)-one 
• 1356829-83-8 (3aR,6aR)-3-(4-chlorophenyl)-6a-methyl-4,5,6,6a-tetrahydropentalen-1(3aH)-one 
• 1356829-85-0 (3aR,6aR)-3-(4-methoxyphenyl)-6a-methyl-4,5,6,6a-tetrahydropentalen-1(3aH)-one 

Relevant articles and documents

Stereoselective migration of sterically hindered organoboranes in cyclic and acyclic systems. A stereoselective allylic C-H activation reaction

The thermal migration of cyclic and acyclic organoboranes were studied. In most cases, a stereoselective 1,2-dyotropic migration was observed, allowing the stereocontrol of three contiguous chiral centers. Scope and limitations of this thermal migration are presented.

Stereoselective construction of the dicyelopenta[a,d]cyclooctene core of the ceroplastin sesterterpenes by way of the anionic oxy-cope rearrangement

Bicyclo[3.2.1]oetanediones such as 9, which are readily available by double carbonylation of (1,3-cyclohexadiene)iron tricarbonyl complexes according to Eilbracht, are amenable to regiospecific methylenation under Wittig conditions. Reduction of 10 with copper hydride leads to 11, which can be resolved by application of Johnson's sulfoximine technology and oxidized to give the enantiopure antipodes of 10. Variously substituted cyclopentenyl anions undergo 1,2-addition to 10, providing carbinols which are capable of anionic oxy-Cope rearrangement via chair transition states. These structural reorganizations are fully stereocontrolled and lead directly to functionalized dicyclopenta[a,d]cyclooctenes. When 11 is treated analogously, only [1,3] sigmatropy is observed and inversion of stereochemistry at the migrating carbon prevails. Both processes exhibit impressive scaffolding powers and are characterized by brevity.

Vinyl Cations, 36. Solvolysis of Cycloalkylidenemethyl and 1-Cyclopenten-1-yl Triflates

Cyclohexylidenemethyl triflate (2), cyclobutylidenemethyl triflate (5), 1-cyclopenten-1-yl triflate (7), bicyclohex-2-en-2-yl triflate (9), 1-cyclobutylideneethyl triflate (19), and 2-methyl-1-cyclopenten-1-yl triflate (29) were solvolyzed in solvents of various ionizing power and nucleophilicity and the solvolysis products were identified.The cyclobutylidenealkyl triflates solvolyze via a vinyl cation mechanism involving ion pairs with rearrangement to cyclopentene and cyclopentanone compounds.The 1-cyclopenten-1-yl triflates do not produce vinyl cation intermediates but give only the corresponding ketones via an O - S bond cleavage of the triflate group.