822-96-8

Basic information

• Product Name: 5-methylbicyclo[2.2.1]hept-2-ene
• Synonyms: Bicyclo(2.2.1)hept-2-ene, 5-methyl-;Einecs 212-509-7;5-Methyl-bicyclo[2.2.1]hept-2-ene (exo/endo Gemisch ~4:6)
• CAS NO: 822-96-8
• Molecular Formula: C₈H₁₂
• Molecular Weight: 108.1809
• EINECS: 212-509-7
• Mol File: 822-96-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 126.7°Cat760mmHg
• Flash Point: 9.8°C
• Appearance: /
• Density: 0.912g/cm³
• Vapor Pressure: 14mmHg at 25°C
• Refractive Index: 1.496
• CAS DataBase Reference: 5-methylbicyclo[2.2.1]hept-2-ene(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methylbicyclo[2.2.1]hept-2-ene(822-96-8)
• EPA Substance Registry System: 5-methylbicyclo[2.2.1]hept-2-ene(822-96-8)

Safety Data

• Hazardous Substances Data: 822-96-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H12/c1-6-4-7-2-3-8(6)5-7/h2-3,6-8H,4-5H2,1H3

Upstream product

• 187737-37-7 propene 
• 1755-01-7 endo-Dicyclopentadien 
• 542-92-7 cyclopenta-1,3-diene 
• 42402-86-8 (1R,4S)-5-Methyl-bicyclo[2.2.1]hept-2-en-7-one 
• 5240-72-2 exo-hydroxymethylnorbornane 
• 497-35-8 2-methylenebicyclo[2.2.1]heptane 
• 694-91-7 5-methylenebicyclo[2.2.1]hept-2-ene 
• 42070-73-5 Toluene-4-sulfonic acid (1S,2R,4S)-1-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester 
• 5453-80-5 5-Norbornene-2-carboxaldehyde 
• 95-12-5 5-hydroxymethyl-2-norbornene 
• 106-95-6 allyl bromide 
• 86646-41-5 (bicyclo[2.2.1]hept-5-en-2-yl)methyl methanesulfonate 
• 95-09-0 5-chloromethyl-2-norbornene 
• 16745-72-5 p-Toluolsulfonsaeure-<6exo-methyl-2exo-norbornyl>ester 

Downstream Products

• 498-66-8 norborn-2-ene 
• 693-89-0 1-methylcyclopent-1-ene 
• 110-83-8 cyclohexene 
• 95-12-5 5-hydroxymethyl-2-norbornene 
• 21681-47-0 9-methyltetracyclo[6.2.1.1^3.6.0^2.7]dodec-4-ene 
• 74-85-1 ethene 
• 542-92-7 cyclopenta-1,3-diene 
• 15185-11-2 2-methylnorbornane 
• 21681-47-0 8-methyltetracyclo<4.4.1^2,5.1^7,10.0^1,6>dodec-3-ene 
• 21681-47-0 8-methyltetracyclo<4.4.1^2,5.1^7,10.0^1,6>dodec-3-ene 

Relevant articles and documents

Scope, limitations and mechanistic aspects in the selective homogeneous palladium-catalyzed reduction of alkenes under transfer hydrogen conditions

A new and efficient mild Pd/P(t-Bu)3 catalyst for selective reduction of various alkenes under transfer hydrogen conditions has been developed leading to the corresponding saturated derivatives in chemical yields varying from 65 to 98%. Mechanistic rationale of this reaction has been also demonstrated.

Thermal rearrangement of 7-methylbicyclo[3.2.0]hept-2-ene: An experimental probe of the extent of orbital symmetry control in the [1,3] sigmatropic rearrangement

The gas-phase thermal rearrangement of exo-7-methylbicyclo[3.2.0]hept-2-ene yields almost exclusively 5-methylnorbornene products. Inversion (i) of configuration dominates this [1,3] sigmatropic shift although some retention (r) is also observed. Because the [1,3] migration can only occur suprafacially (s) in this geometrically constrained system, the si/sr ratio of 7 observed for the migration of C7 in exo-7-methylbicyclo[3.2.0]hept-2-ene indicates that the orbital symmetry rules are somewhat permissive for the [1,3] sigmatropic migration of carbon.

Substituent Effects on 1H Chemical Shifts I-Complete 1H Chemical Shift Assignments of Methyl-Substituted Cyclic Systems

1H chemical shift assignments are presented for 2-methyladamantane, 2-methylnorbornane (endo and exo) and 2-methylnorbornene (endo and exo).Resonance assignment was achieved using a variety of 1D and 2D homo- and heteronuclear (1H-13C)experiments.The methyl group-induced substituent chemical shift (SCS) is derived and the SCS of protons vicinal to this group is discussed.KEY WORDS Norbornanes Norbornenes Adamantanes 1H NMR Substituent chemical shifts