36439-78-8

Basic information

• Product Name: 2,3-dimethylidenebicyclo[2.2.1]heptane
• Synonyms: 2,3-Bis(methylene)bicyclo[2.2.1]heptane; Bicyclo(2.2.1)heptane, 2,3-bis(methylene)-; bicyclo[2.2.1]heptane, 2,3-bis(methylene)-
• CAS NO: 36439-78-8
• Molecular Formula: C₉H₁₂
• Molecular Weight: 120.1916
• Mol File: 36439-78-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 156.1°C at 760 mmHg
• Flash Point: 29.1°C
• Density: 0.91g/cm³
• Vapor Pressure: 3.78mmHg at 25°C
• Refractive Index: 1.5
• CAS DataBase Reference: 2,3-dimethylidenebicyclo[2.2.1]heptane(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-dimethylidenebicyclo[2.2.1]heptane(36439-78-8)
• EPA Substance Registry System: 2,3-dimethylidenebicyclo[2.2.1]heptane(36439-78-8)

Safety Data

• Hazardous Substances Data: 36439-78-8(Hazardous Substances Data)

Usage

Bicyclic structure

2,3-dimethylidenebicyclo[2.2.1]heptane has a unique bicyclic structure containing a total of seven carbon atoms.

Methylidene groups

The compound possesses two methylidene (CH2) groups, which are known for their unique reactivity and stability.

Stability

2,3-dimethylidenebicyclo[2.2.1]heptane is highly stable.

Precursor in organic synthesis

It is used as a precursor in the synthesis of various organic compounds.

Model compound for carbene reactivity and stability

The compound can act as a model compound for studying the reactivity and stability of carbenes in organic chemistry.

Potential use in pharmaceutical and materials science research

Due to its unique structure and reactivity, 2,3-dimethylidenebicyclo[2.2.1]heptane has been investigated for its potential use in pharmaceutical and materials science research.

Upstream product

• 108148-11-4 3,6-Dioxo-cyclohexa-1,4-diene-1,2-dicarbonitrile; compound with 2,3-dimethylene-bicyclo[2.2.1]heptane 
• 108120-80-5 2,3-Dicyano-but-2-enedinitrile; compound with 2,3-dimethylene-bicyclo[2.2.1]heptane 

Downstream Products

• 108148-11-4 3,6-Dioxo-cyclohexa-1,4-diene-1,2-dicarbonitrile; compound with 2,3-dimethylene-bicyclo[2.2.1]heptane 
• 3467-63-8 2-Methyl-3-p-tolylsulfanylmethyl-bicyclo[2.2.1]hept-2-ene 
• 28626-68-8 2endo,3endo-dimethyl-norbornane 
• 876-05-1 cis-1,3-cyclopentanedicarboxylic acid 
• 529-16-8 santene 
• 16144-91-5 1,2,3,4-tetrahydro-1,4-methanonaphthalene-5,8-diol 

Relevant articles and documents

Charge-Transfer Complexes and Reactivity in Diels-Alder Cycloadditions

The reactivity of 2,3-bis(methylene)norbornane (1) towards the highly reactive dienophiles 2,3-dicyano-p-benzoquinone (2), tetracyanoethylene (3), 2,3-dicyanomaleimide (4), and p-benzoquinone-2,3-dicarboxyclic anhydride (5) was analysed kinetically.CT complexes were observed for 1 with 2-5 and equilibrium constants for the formation of the CT complexes between 1 and 2-4 were determined kinetically.The relationship between relative rates, CT-excitation energies, HOMO-LUMO separations, and CT-complex equilibrium constants is discussed.The results do not require the CT complexes to be intermediates but strongly support the importance of CT interactions in the transition state of these cycloadditions.