285-58-5

Basic information

• Product Name: bicyclo(3.1.0)hexane
• Synonyms: bicyclo(3.1.0)hexane;Norsabinane;Northujane
• CAS NO: 285-58-5
• Molecular Formula: C₆H₁₀
• Molecular Weight: 82.14
• Mol File: 285-58-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 85.05°C (rough estimate)
• Flash Point: °C
• Appearance: /
• Density: 0.9100 (rough estimate)
• Vapor Pressure: 87.6mmHg at 25°C
• Refractive Index: 1.5480 (estimate)
• CAS DataBase Reference: bicyclo(3.1.0)hexane(CAS DataBase Reference)
• NIST Chemistry Reference: bicyclo(3.1.0)hexane(285-58-5)
• EPA Substance Registry System: bicyclo(3.1.0)hexane(285-58-5)

Safety Data

• Hazardous Substances Data: 285-58-5(Hazardous Substances Data)

Usage

General Description

Bicyclo(3.1.0)hexane is a bicyclic organic compound with a unique structure consisting of three carbon atoms forming a bridge between two cyclohexane rings. It is a colorless liquid with a characteristic odor, and it is often used as a versatile building block in the synthesis of various organic compounds. Bicyclo(3.1.0)hexane has been studied for its potential application in pharmaceuticals, as well as in the production of polymers and other industrial chemicals. It is known for its stability and ability to undergo various chemical reactions, making it a valuable compound in organic chemistry research and industrial processes.

InChI:InChI=1/C6H10/c1-2-5-4-6(5)3-1/h5-6H,1-4H2

Upstream product

• 75-89-8 2,2,2-trifluoroethanol 
• 99810-99-8 cis-3-(trimethylsilyl)cyclohexyl brosylate 
• 39967-13-0 trans-1,3-bis(methansulfonyloxy)cyclohexan 
• 39967-13-0 cis-1,3-bis(methansulfonyloxy)cyclohexan 
• 139409-09-9 (E/Z)-1-Chloro-6-iodo-1-hexene 
• 3725-17-5 1,3-dibromocyclohexane 
• 64-17-5 ethanol 

Downstream Products

• 136773-22-3 trans-1-t-butylperoxy-3-iodocyclohexane 
• 89489-26-9 (1R,5S)-bicyclo[3.1.0]hexan-3-ol 
• 13668-59-2 3-hydroxymethyl-cyclopentene 
• 822-66-2 3-cyclohexen-1-ol 
• 1755-04-0 bicyclo[3.1.0]hexan-3-one 
• 89489-26-9 bicyclo[3.1.0]hexane-3-ol 
• 822-58-2 endo-2-bicyclo<3.1.0>hexanol 
• 822-58-2 cis-2-bicyclo[3.1.0]hexanol 
• 694-43-9 (1R,3r,5S)-bicyclo[3.1.0]hexan-3-ol 
• 693-89-0 1-methylcyclopent-1-ene 
• 622-45-7 cyclohexyl acetate 
• 1120-62-3 3-methyl-1-cyclopentene 
• 24070-76-6 cis-2-methylcyclopentyl acetate 
• 24070-76-6 trans-2-methylcyclopentanol acetate 

Relevant articles and documents

Formation of Cyclopropanes via Activation of (γ-Methoxy)alkyl Gold(I) Complexes with Lewis Acids

Treatment of the gold 3-methoxy-3-phenylpropyl complex (P)AuCH2CH2CH(OMe)Ph [P = P(t-Bu)2o-biphenyl] with AlCl3 at -78 °C led to the immediate (≤5 min) formation of a 4:1 mixture of phenylcyclopropane and (1-methoxypropyl)benzene in 86 ± 5% combined yield. Lewis acid activation of the stereochemically pure isotopomer erythro-(P)AuCH2CHDCH(OMe)Ph led to the formation of cis-2-deuterio-1-phenylcyclopropane in 84 ± 5% yield as a single stereoisomer, which established that cyclopropanation occurred with inversion of the γ-stereocenter. Similarly, ionization of the stereochemically pure cyclohexyl gold complex cis-(P)AuCHCH2CH(OMe)CH2CH2CH2 at -78 °C formed bicyclo[3.1.0]hexane in 82% ± 5% yield, which validated a low energy pathway for cyclopropanation involving inversion of the α-stereocenter. Taken together, these observations are consistent with a mechanism for cyclopropane formation involving backside displacement of both the Cγleaving group and the Cα (L)Au+ fragment via a W-shaped transition state.

Generation of a Carbenoid by Cyclization of 6-Chloro-5-hexen-1-yllithium

Bicyclohexane and methylenecyclopentane, products deriving from an apparent carbenoid intermediate, have been observed in the intramolecular cyclization reaction of 6-chloro-5-hexen-1-yllithium.

Elektroreduktion organischer Verbindungen, 14. Die elektrochemische Reduktion von 1,3-Bis(methansulfonyloxy)cyclohexanen.

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