4313-36-4

Basic information

• Product Name: 5-chlorobicyclo[2.2.1]hept-2-ene
• CAS NO: 4313-36-4
• Molecular Formula: C₇H₉Cl
• Molecular Weight: 128.5994
• Mol File: 4313-36-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 174.2°C at 760 mmHg
• Flash Point: 42.9°C
• Density: 1.13g/cm³
• Vapor Pressure: 1.63mmHg at 25°C
• Refractive Index: 1.53
• CAS DataBase Reference: 5-chlorobicyclo[2.2.1]hept-2-ene(CAS DataBase Reference)
• NIST Chemistry Reference: 5-chlorobicyclo[2.2.1]hept-2-ene(4313-36-4)
• EPA Substance Registry System: 5-chlorobicyclo[2.2.1]hept-2-ene(4313-36-4)

Safety Data

• Hazardous Substances Data: 4313-36-4(Hazardous Substances Data)

Upstream product

• 694-97-3 endo-5-norbornen-2-ol 
• 75-01-4 chloroethylene 
• 542-92-7 cyclopenta-1,3-diene 

Relevant articles and documents

Endo entry to the nortricyclyl-norbornenyl cation system: Stereochemistry in the fragmentation of endo-5-norbornenyl-2-oxychlorocarbene

Fragmentation of (S)-endo-5-norbornenyl-2-oxychlorocarbene [(S)-8] in cyclohexane-d12 gives ～20% (S)-endo-2-chloro-5-norbornene [(S)-7] with ～50% ee, 65-70% (R)-exo-2-chloro-5-norbornene [(R)-4] with >95% ee, and ～12% (R)-3-nortricyclyl chloride [(R)-5] with ～22% ee. (Analogous stereochemical results were also obtained starting with the enantiomeric carbene (R)-8.) The (S)-8 to (S)-7 and (S)-8 to (R)-4 conversions are ascribed mainly to retention and inversion SNi transition states, respectively. These have been located by computational methods and are nearly isoenergetic. In more polar solvents (CDCl3 and CD3CN), the fragmentation of (S)-8 increasingly occurs via competitive ion pair pathways in which steroselectivity is diminished, and escape to the norbornenyl-nortricyclyl cation directs the products away from endo-2-chloro-5-norbornene toward exo-chloride 4 and nortricyclyl chloride 5.