497-28-9

Basic information

• Product Name: 5,5-Dimethylnorborna-2-ene
• Synonyms: 5,5-Dimethylbicyclo[2.2.1]hept-2-ene;5,5-Dimethylnorborna-2-ene;Apoisofenchene
• CAS NO: 497-28-9
• Molecular Formula: C9H14
• Molecular Weight: 122.21
• Mol File: 497-28-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 27-28 °C
• Boiling Point: 140-141 °C(Press: 762 Torr)
• Appearance: /
• Density: 0.8678 g/cm3
• CAS DataBase Reference: 5,5-Dimethylnorborna-2-ene(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5-Dimethylnorborna-2-ene(497-28-9)
• EPA Substance Registry System: 5,5-Dimethylnorborna-2-ene(497-28-9)

Safety Data

• Hazardous Substances Data: 497-28-9(Hazardous Substances Data)

Upstream product

• 258264-50-5 5,5-dimethyl-norbornan-2-ol 
• 32190-82-2 (+/-)-2-methyl-norborn-5-ene-2exo-carboxylic acid 
• 92007-58-4 (1S)-endo-2-methylbicyclo<2.2.1>hept-5-ene-2-carboxylic acid 
• 534-36-1 β-fenchocamphorone 
• 91573-15-8 Toluene-4-sulfonic acid 2-methyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester 
• 91605-21-9 (1S-exo)-2-methylbicyclo<2.2.1>hept-5-ene-2-methanol 
• 40441-67-6 5-formyl-5-methylbicyclo[2.2.1]hept-2-ene 
• 58728-89-5 6,6-Dimethylbicyclo<2.2.1>heptan-2-on-p-tolylsulfonylhydrazon 

Downstream Products

• 38476-45-8 6,6-dimethyl-2-norbornanone 
• 22426-01-3 2,6,6-trimethyl-endo-2-norbornyl p-nitrobenzoate 
• 111329-45-4 (+/-)-phthalic acid mono-(5,5-dimethyl-[2exo]norbornyl ester) 
• 534-36-1 β-fenchocamphorone 

Relevant articles and documents

4. NORBORNANES. PART 19. THE INDUCTIVE MODEL FOR NORBORNYL CATION FORMATION

Two CH3 groups at C(6) of 2-exo- (10a) and 2-endo-norbornyl p-toluenesulfonate 11a lower their solvolysis rates in 80 percent EtOH by factors of 28 and 16, respectively.A spirocyclopropyl group including C(6), as in 21a and 22a, reduces the rate of exo- and endo-ionization by factors of 250 and 8, respectively.The geminally dimethyl-substituted tosylates 10a and 11a yield the 2-exo-alcohol 10b, whereas the spirocycclopropyl-substituted tosylates 21a and 22a furnish rearranged 3-brendanol 23.These findings are readily rationalized by the inductive model, according to which norbornyl cation formation is controlled by the inductive effect of dorsal substituents.

Deamination Reactions, 40. Decomposition of 3,3-, 5,5-, and 7,7-Dimethyl-2-norbornanediazonium Ions

gem.-Dimethylnorbornyl cations (3, 5) were generated by decomposition of optically active diazonium ion precursors. 6,1- and 6,2-H shifts were detected by structural isomerization and racemization, respectively.Product distributions and optical activities were profoundly affected by the polarity of the solvent.In weakly polar solvents, substitution reactions were associated with much less racemization than hydrogen shifts.Our observations are incompatible with equilibrating open ions but are reasonably explained in terms of unsymmetrical ion pairs.