148683-89-0

Basic information

• Product Name: Bicyclo[2.2.1]heptane-2-carbonitrile, 2-hydroxy-6-methyl-, (2-endo,6-exo)- (9CI)
• Synonyms: Bicyclo[2.2.1]heptane-2-carbonitrile, 2-hydroxy-6-methyl-, (2-endo,6-exo)- (9CI)
• CAS NO: 148683-89-0
• Molecular Formula: C9H13NO
• Molecular Weight: 151.20562
• Product Categories: CYCLOPENTANE
• Mol File: 148683-89-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 287.0±23.0 °C(Predicted)
• Appearance: /
• Density: 1.13±0.1 g/cm3(Predicted)
• PKA: 11.46±0.40(Predicted)
• CAS DataBase Reference: Bicyclo[2.2.1]heptane-2-carbonitrile, 2-hydroxy-6-methyl-, (2-endo,6-exo)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[2.2.1]heptane-2-carbonitrile, 2-hydroxy-6-methyl-, (2-endo,6-exo)- (9CI)(148683-89-0)
• EPA Substance Registry System: Bicyclo[2.2.1]heptane-2-carbonitrile, 2-hydroxy-6-methyl-, (2-endo,6-exo)- (9CI)(148683-89-0)

Safety Data

• Hazardous Substances Data: 148683-89-0(Hazardous Substances Data)

Upstream product

• 87494-99-3 exo-6-Methylbicyclo<2.2.1>heptan-2-on 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 

Relevant articles and documents

Rearrangements of 1- and 2-Cyano-2-norbornyl Cations

Sulfonates of exo-2-hydroxynorbornane-endo-2-carbonitrile (2c-e) were found to rearrange exothermally to give sulfonates of exo-2-hydroxynorbornane-1-carbonitrile (6c-e), solvolysis being a minor side reaction.In contrast, the analogous endo substrates (3c-e) afforded the rearranged alcohol 6a and tricyclo2,6>heptane-1-carbonitrile (4) as the major products.We have not been able to trap 2-cyano-2-norbornyl cations by external nucleophiles or by internal 6,2-shifts of hydrogen or carbon.On the other hand, there is good evidence for the generation of 1-cyano-2-norbornyl cations from both 3d, e and 6e.The degenerate 6,2-H shift in these species has been uncovered by means of labeled or optically active precursors.The 1-CN substituent clearly promotes the 6,2-H shift relative to the parent 2-norbornyl cation, but is inferior to 1-C2F5.Ring expansion of a spiroannelated cyclopropane, involving a 6,2-H shift of carbon, was also observed (25, 26 -> 27, 28).Our data strongly suggest that 2-cyano-2-norbornyl cations are less stable than 1-cyano-2-norbornyl cations.The reaction rates of 2c versus 6c do not reflect the stability of the incipient carbocations, owing to the large difference in ground state energy.Key Words: Carbocations, destabilized / Solvolysis / Wagner-Meerwein rearrangement / 6,2-H Shifts / Ring Expansion