765-90-2

Basic information

• Product Name: (2R)-2-methylbicyclo[2.2.1]heptane
• CAS NO: 765-90-2
• Molecular Formula: C₈H₁₄
• Molecular Weight: 110.1968
• Mol File: 765-90-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 129.3°C at 760 mmHg
• Flash Point: 13.4°C
• Density: 0.88g/cm³
• Vapor Pressure: 12.5mmHg at 25°C
• Refractive Index: 1.471
• CAS DataBase Reference: (2R)-2-methylbicyclo[2.2.1]heptane(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2-methylbicyclo[2.2.1]heptane(765-90-2)
• EPA Substance Registry System: (2R)-2-methylbicyclo[2.2.1]heptane(765-90-2)

Safety Data

• Hazardous Substances Data: 765-90-2(Hazardous Substances Data)

Upstream product

• 6518-44-1 (+/-)-2endo-chloromethyl-norbornane 
• 58001-75-5 2-methylenebicyclo<2.2.1>heptane 
• 13137-31-0 endo-2-Bicyclo<2.2.2>heptylmethanol 
• 95-09-0 5-chloromethylbicyclo[2,2,1]hep-2-ene 
• 143493-98-5 Methanesulfonic acid 3-vinyl-hex-5-enyl ester 
• 3197-78-2 2-methyl-2-norbornyl cation 
• 143493-99-6 3-(2-iodoethyl)-1,5-hexadiene 
• 1460-24-8 3-Methyltricyclo<2.2.1.0^2,6>heptan 
• 134628-16-3 cis-1-ethenyl-3-(iodomethyl)cyclopentane 
• 62078-84-6 bicyclo[2.2.1]heptan-2-ylmethyl methanesulfonate 

Downstream Products

• 6221-55-2 bicyclo[3.2.1]octane 
• 10052-18-3 1-Methylbicyclo[2.2.1]heptane 
• 694-72-4 bicyclo[3.3.0]octane 

Relevant articles and documents

Carbon-13 NMR and IR Spectroscopic Studies on Some 7-Oxabicycloheptanes and -heptenes. n-? Interaction and Hydrogen Bonding

The 13C NMR spectra of diastereomeric pairs of the title compounds together with some tetrahydrofurans were examined and the chemical shifts were compared with those for the corresponding bicycloheptanes and -heptenes.The intramolecular interaction between the n-orbital of an oxygen atom and the ?-orbital of an olefinic bond was found in 2-methylene-7-oxabicycloheptane.Intramolecular hydrogen bonding between the 7-oxygen and the hydroxyl group occurs in exo-7-oxabicycloheptane-2-methanol.

Highly stereoselective tandem cyclizations of 5-hexenyllithiums: Preparation of endo-2-substituted bicyclo[2.2.1]heptanes and 3-substituted trans-bicyclo[ 3.3.0] octanes

Tandem cyclization of diolefinic alkyllithiums, derived from acyclic diolefinic alkyl iodides by low-temperature lithium-iodine exchange, proceeds via two highly stereoselective and totally regiospecific 5-exo-trig ring closures to deliver bicyclic alkyllithiums. Trapping of the organolithium product by addition of an electrophile cleanly affords functionalized bicyclic molecules in good yield. In this way both endo-2-substituted bicyclo[2.2.1]heptanes and 3-substituted trans-bicyclo[3.3.0]octanes have been prepared in isolated yields of 65-80% from the readily available 3-(2-iodoethyl)-1,5-hexadiene (5) and 7-iodo-4-ethenyl-1-heptene (9), respectively. Attempts to effect tandem cyclization of 5,10-undecadienyllithium (11), which would be mediated by a secondary alkyllithium species, were unsuccessful. The results suggest that tandem anionic cyclization provides a convenient route to a variety of bicyclic systems not readily available by other approaches.

Optical and Neutron Inelastic Scattering Study of 2-Methylnorbornanes

We have measured the infrared, Raman, and neutron vibrational spectra of the 2-methylnorbornanes with a CH3 or CD3 methyl group in the exo or endo position.A normal coordinate analysis has been carried out.The torsional modes of the methyl group are assigned at 240 and 235 cm-1 for the hydrogenated exo and endo isomers, respectively.The corresponding barrier is 15.2 +/- 0.2 kJ mol-1.The calculated neutron intensities are in good agreement with the experimental data.The frequencies are used for the determination of the thermodynamic contribution to the standard free energy difference.