766-25-6

Basic information

• Product Name: Bicyclo[2.2.1]heptan-2-ol, 1-methyl-, exo-
• CAS NO: 766-25-6
• Molecular Formula: C8H14O
• Molecular Weight: 126.199
• Mol File: 766-25-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Bicyclo[2.2.1]heptan-2-ol, 1-methyl-, exo-(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[2.2.1]heptan-2-ol, 1-methyl-, exo-(766-25-6)
• EPA Substance Registry System: Bicyclo[2.2.1]heptan-2-ol, 1-methyl-, exo-(766-25-6)

Safety Data

• Hazardous Substances Data: 766-25-6(Hazardous Substances Data)

Upstream product

• 149-57-5 2-Ethylhexanoic acid 
• 51655-31-3 endo-2-Methylbicyclo<2.2.1>hept-exo-2-ylamin 
• 51655-31-3 exo-2-Methylbicyclo<2.2.1>hept-endo-2-ylamin 
• 64-19-7 acetic acid 
• 88798-96-3 1-methyl-exo-2-norbornylamine 
• 88798-96-3 endo-2-amino-1-methylbicyclo<2.2.1>heptane 
• 13351-35-4 1-Methylbicyclo<2.2.1>hept-endo-2-yl-p-methylbenzolsulfonat 
• 88799-09-1 1-Methylbicyclo<2.2.1>hept-endo-2-yl-2,2,2-trifluorethansulfonat 
• 38996-55-3 exo-2-methylbicyclo<3.1.1>heptan-2-ol 
• 87030-94-2 2-methoxy-2-methylbicyclo<3.1.1>heptane 
• 88798-95-2 1-methylbicyclo<2.2.1>hept-endo-2-yl p-bromobenzenesulfonate 
• 88799-08-0 1-Methylbicyclo<2.2.1>hept-endo-2-yl-4-nitrobenzolsulfonat 
• 87030-96-4 2-Methylbicyclo<3.1.1>hept-2-ylamin 
• 127-09-3 sodium acetate 

Downstream Products

• 18366-92-2 (+/-)-phthalic acid mono-(1-methyl-[2exo]norbornyl ester) 
• 18366-92-2 (+/-)-phthalic acid mono-(1-methyl-[2endo]norbornyl ester) 
• 497-35-8 2-methylenebicyclo[2.2.1]heptane 
• 694-92-8 2-methylnorborn-2-ene 
• 822-73-1 1-methyl-norborn-2-ene 
• 10218-04-9 1-methyl-norbornan-2-one 
• 4601-85-8 1-methyltricyclo<2.2.1.0^2,6>heptane 

Relevant articles and documents

34. Norbornanes Part 20 Inductivity and Bridging in 2-Norbornyl Cations

The solvolysis rates and products of several 1-substituted 2-exo- and 2-endo-norbornyl p-toluenesulfonates 7 and 8, respectively, have been determined.Hydrolyses of these epimeric tosylates yielded rearranged products in varying amounts, except when the substituent was COOCH3 or CN.The logarithms of the rate constants (log k) for the endo-series 8 correlated linearly with the corresponding inductive constants ?q1 with a reaction constant ρ1 of -1.24.On the other hand, log k values for the exo-series 7 appear to fit two regression lines,the first line (ρ1 = -1.90) defined by the tosylates that ionize, with rearrangement, to the tertiary cations 11, the second (ρ1 = -1.86) by the tosylates 7(R = H, COOCH3, and CN) that ionize to an asymetrically bridged secondary cation 19.These results confirm the unique participation of C(6) with a ρ1 of -2.00 in the ionization of 2-exo-norbornyl tosylate.

Norpinyl-Norbornyl Rearrangements: 2-Methyl- and 2,exo-6-Dimethylbicycloheptane Derivatives

Solvolyses of 2-methylbicyclohept-2-yl-4-nitrobenzoate (9), the nitrous acid deamination of the corresponding amine (4e), and acid-catalyzed rearrangements of various 2-methylbicycloheptane derivatives (4a - c) have been investigated. 2-Methylbicycloheptyl (4) and 1-methyl-endo-2-norbornyl (10) products prevailed; minor quantities of 2-methyl-exo-2-norbornyl derivatives (12) were also obtained.The product distributions were independent of the precursor but were strongly affected by the nucleophilicity of the solvent.Our observations are consistent with the 7-bridged norbornyl cation 6 as the predominant intermediate.Further stabilization of 6 by exo-3-methyl substitution is indicated by the results of the acid-catalyzed rearrangement of 2,exo-6-dimethylbicycloheptan-2-ol (17).