25093-48-5

Basic information

• Product Name: 6-ethenylbicyclo[2.2.1]hept-2-ene
• Synonyms: 2-Norbornene,5-vinyl-, endo- (8CI); Bicyclo[2.2.1]hept-2-ene, 5-ethenyl-, endo-;endo-2-Vinyl-5-norbornene; endo-5-Vinyl-2-norbornene;endo-5-Vinylbicyclo[2.2.1]hept-2-ene
• CAS NO: 25093-48-5
• Molecular Formula: C₉H₁₂
• Molecular Weight: 120.19
• Mol File: 25093-48-5.mol

Chemical Properties

• Boiling Point: 141°Cat760mmHg
• Flash Point: 26.2°C
• Appearance: /
• Density: 1.006g/cm³
• CAS DataBase Reference: 6-ethenylbicyclo[2.2.1]hept-2-ene(CAS DataBase Reference)
• NIST Chemistry Reference: 6-ethenylbicyclo[2.2.1]hept-2-ene(25093-48-5)
• EPA Substance Registry System: 6-ethenylbicyclo[2.2.1]hept-2-ene(25093-48-5)

Safety Data

• Hazardous Substances Data: 25093-48-5(Hazardous Substances Data)

Upstream product

• 3048-64-4 exo-vinylnorbornene 
• 3048-64-4 endo-vinylnorbornene 
• 77-73-6 bi(cyclopentadiene) 
• 106-99-0 buta-1,3-diene 
• 542-92-7 cyclopenta-1,3-diene 
• 3048-64-4 5-vinyl-bicyclo[2.2.1]hept-2-ene 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 5453-80-5 exo-2-formylbicyclo[2.2.1]hept-5-ene 

Downstream Products

• 542-92-7 cyclopenta-1,3-diene 
• 106-99-0 buta-1,3-diene 
• 100-40-3 4-ethenylcyclohexene 
• 3048-65-5 bicyclo[4.3.0]nona-3,7-diene 
• 3048-64-4 5-vinyl-2-norbornene 
• 77-73-6 dicyclopentadiene 
• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 2886-87-5 exo-2,3-epoxy-5-vinylbicyclo[2.2.1]heptane 
• 83988-54-9 2-(5-norbornen-endo-2-yl)ethyl p-toluenesulfonate 
• 3048-64-4 5-vinyl-8,9,10-trinorborn-2-ene 
• 28304-67-8 5-ethylidene-2-norbornene 
• 2146-41-0 exo-2-ethyl-bicyclo-/2.2.1/heptane 
• 2146-41-0 endo-2-ethylnorbornane 
• 2886-87-5 (1R,5R,6R)-6-Vinyl-3-oxa-tricyclo[3.2.1.0^2,4]octane 

Relevant articles and documents

Ultrahigh Tg Epoxy Thermosets Based on Insertion Polynorbornenes

Thermosetting materials (thermosets) are widely used organic materials derived from 3D-network forming monomers. Achieving high glass transition temperature (Tg) thermosets is often a challenging task due to the complexity of designing efficiently and cheaply monomers which are rigid enough to prevent molecular motions within the thermoset. We report here a very simple route to prepare epoxy thermosets with Tg as high as 350 °C, based on insertion polynorbornenes. The epoxy monomer (PNBE(epoxy)) is prepared by the epoxidation of poly(5-vinylnorbornene) obtained by catalytic insertion polymerization of 5-vinylnorbornene. PNBE(epoxy) can be cross-linked with simple biosourced compounds. Alternatively, polar insertion polynorbornene can also be used as cross-linker in the formulation of an epoxy resin, once again resulting in epoxy resins with Tg higher than 300 °C and devoid of degradation at this temperature. Thus, this study clearly demonstrates the viability of catalytic polymerization to access epoxy thermosets with ultrahigh Tg.

PROCESS FOR PRODUCING HIGH PURITY EXO-ALKENYLNORBORNENE

Embodiments of the present invention are directed generally to methods for producing high purity exo-alkenylnorbornenes from a mixture of conformational isomers thereof.

Application of molecular dynamics to chromatographic-spectral identification of isomeric products of organic reactions

Isomeric products of [2+4]-cycloaddition reactions can be identified by gas chromatography-mass spectrometry on the basis of their experimental retention parameters and intramolecular vibrational and rotational energies (E) calculated by molecular mechanics for all possible isomers. The Chromatographic parameters change in the opposite direction with respect to E. The proposed approach allows unambiguous identification of four products formed by each of the reactions of butadiene with cyclopentadiene, of isoprene with 2,3-dimethylbutadiene, of cyclopentadiene with isoprene, and dimerization of isoprene and two of the four products formed by the reaction of 1,3-cyclohexadiene with cyclopentadiene. Both structural and steric isomers (exo, endo) can be distinguished. 1998 MAHK "Hayka/Interperiodica".

Useful Synthetic Routes to Pure exo-5-Vinyl-2-norbornene and endo-5-Vinyl-2-norbornene

Hydroboration of 5-vinyl-2-norbornene (1) with 9-BBN mainly affords 5-(2-hydroxyethyl)-2- norbornene (2).The iodo ether cyclization of 2 can convert only endo-5-(2-hydroxyethyl)-2-norbornene (2b) to iodo ether 10, followed by reductive elimination and subsequent dehydration to furnish endo-5-vinyl-2-norbornene (1b) which has not been isolated in pure form.Meanwhile, unreacted exo-5-(2-hydroxyethyl)-2-norbornene (2a) produces exo-5-vinyl-2-norbornene (1a) via dehydration.