287-13-8

Usage

Type of compound

Saturated cyclic hydrocarbon

Structure

Six-membered ring with a triple bond between the first and second carbon atoms

Usage

Building block in organic synthesis

Applications

Production of pharmaceuticals, agrochemicals, and specialty chemicals

Reactivity

Unique and versatile

Additional use

Starting material for the synthesis of other chemical compounds

Industrial application

Solvent in the paint and coatings industry

Environmental and health considerations

Careful management during production, handling, and disposal due to potential impacts

InChI:InChI=1/C7H10/c1-2-4-6-5(3-1)7(4)6/h4-7H,1-3H2

Upstream product

• 60-29-7 diethyl ether 
• 2415-79-4 7,7-dibromonorcarane 
• 823-69-8 7,7-dichloro-bicyclo[4.1.0]heptane 
• 2415-79-4 7,7-dibromonorcarane 
• 920-39-8 isopropylmagnesium bromide 
• 676-58-4 methylmagnesium chloride 
• 925-90-6 ethylmagnesium bromide 
• 3045-87-2 7,7-Dibrom-3-methyl-bicyclo<4.1.0>heptan 

Downstream Products

• 96866-02-3 3-(2-Cyclohexen-1-yl)-1,1,2,2-cyclopropantetracarbonitril 
• 57293-39-7 1-Phenyltricyclo<4.1.0.0.^2,7>heptane 
• 126978-58-3 1-Chlor-2-(tricyclo<4.1.0.0^2,7>hept-1-yl)benzol 
• 886-66-8 1,4-diphenyl-1,3-butadiyne 
• 63846-85-5 1-bromo-tricyclo<4.1.0.0^2,7>heptane 
• 126978-85-6 1-(Phenylethinyl)tricyclo<4.1.0.0^2,7>heptan 
• 132200-59-0 6-endo-p-tolylsulfonyl-7-anti-chloronorpinane 
• 132114-85-3 6-endo-p-tolylsulfonyl-7-syn-chloronorpinane 
• 80476-49-9 Diphenylbis(tricyclo<4.1.0.0^2,7>hept-1-yl)silan 
• 87568-92-1 (1S,5R,6S)-1-Bicyclo[3.1.1]hept-6-yl-propan-2-one 
• 132200-58-9 6-endo-phenylsulfonyl-7-anti-bromonorpinane 
• 132114-84-2 6-endo-phenylsulfonyl-7-syn-bromonorpinane 
• 126978-57-2 1-Chlor-3-(tricyclo<4.1.0.0.^2,7>hept-1-yl)benzol 
• 126978-56-1 1,3-Di(tricyclo<4.1.0.0^2,7>hept-1-yl)benzol 

Relevant academic research and scientific papers

Bromine-magnesium exchange in gem-dibromocyclopropanes using Grignard reagents

Reaction of gem-dibromocyclopropanes with ethylmagnesium bromide at ambient temperature leads to very high yields of allenes; when cyclopropylidene-allene ring opening is suppressed, alternative carbenic products are observed, although other reactions compete. When the reactions are carried out at -60°C, a 1-bromo-1-(bromomagnesio)-cyclopropane is formed which may be trapped by a number of electrophiles.

REACTIONS OF gem-DIBROMOCYCLOALKANES WITH METHYLLITHIUM

In the reaction of 7,7-dibromonorcarane with methyllithium tricyclo2,7>heptane, 7-(1-ethoxyethyl)bicycloheptane, and 7,7-bisnorcaranylidene are formed, and the proportions of these depnd on the reaction temperature.Substituted gem-dibromobicycloheptanes react analogously. 6,6-Dibromobicyclohexanes substituted in the 1 position react with methyllithium with the formation of 3,12-disubstituted tricyclo2,7>dodeca-2,12-dienes.

GENERATION OF CYCLOPROPYLIDENES FROM GEM-DIHALOPROPANES UNDER ULTRASONIC IRRADIATION

Cyclopropylidenes can be generated much quickly by reactions of gem-dihalocyclopropanes and metals (Li, Na or Mg) under ultrasonic irradiation.The reactions usually complete in 5-15 min at room temperature.