872-78-6

Basic information

• Product Name: 2-methylbicyclo[2.2.1]heptane
• Synonyms: Bicyclo[2.2.1]heptane, 2-methyl-; Norbornane, 2-methyl-
• CAS NO: 872-78-6
• Molecular Formula: C₈H₁₄
• Molecular Weight: 110.1968
• Mol File: 872-78-6.mol
• Article Data: 9

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: 2-methylbicyclo[2.2.1]heptane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methylbicyclo[2.2.1]heptane(872-78-6)
• EPA Substance Registry System: 2-methylbicyclo[2.2.1]heptane(872-78-6)

Safety Data

• Hazardous Substances Data: 872-78-6(Hazardous Substances Data)

Upstream product

• 498-66-8 norborn-2-ene 
• 75917-32-7 methylazodiphenylmethanol 
• 62078-84-6 bicyclo[2.2.1]heptan-2-ylmethyl methanesulfonate 
• 1460-24-8 3-Methyltricyclo<2.2.1.0^2,6>heptan 
• 143493-99-6 3-(2-iodoethyl)-1,5-hexadiene 
• 58001-75-5 2-methylenebicyclo<2.2.1>heptane 
• 143493-98-5 Methanesulfonic acid 3-vinyl-hex-5-enyl ester 
• 13118-79-1 exo-2-Bicyclo<2.2.2>heptylmethanol 

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

New functionalized vinyl monomers by ethylene-(functionalized)-norbornene hetero-trimerization catalyzed by cobalt(II)-(imino)pyridine complexes

On activation by MAO the (imino)pyridine cobalt(II) complex CoCl 2N2Ph/i-Pr2 catalyzes the enchainment of one norbornene (NB) molecule with two ethylene molecules to give exo-2,exo-3-ethylvinylnorbornane with high activity and complete diastereoselectivity. Turnover frequencies [TOF, mol NB (mol Co×h) -1] as high as 270,000 have been obtained. The 2E-1NB hetero-trimerization reaction has been also accomplished with NBs bearing polar substituents such as norbornenemethanol and norbornenecarboxylic acid provided that the substrate is protected with triisobutylaluminum and the less sterically demanding complex CoCl2N2Ph/Me2 is used as catalyst precursor. A mechanism for the hetero-trimerization reactions is proposed on the basis of experimental evidence.

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.

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.