7176-92-3

Basic information

• Product Name: anti-7-chloro-2-norbornanone
• CAS NO: 7176-92-3
• Molecular Weight: 144.601
• Mol File: 7176-92-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: anti-7-chloro-2-norbornanone(CAS DataBase Reference)
• NIST Chemistry Reference: anti-7-chloro-2-norbornanone(7176-92-3)
• EPA Substance Registry System: anti-7-chloro-2-norbornanone(7176-92-3)

Safety Data

• Hazardous Substances Data: 7176-92-3(Hazardous Substances Data)

Upstream product

• 498-66-8 norborn-2-ene 
• 3509-46-4 3-nortricyclyl chloride 
• 38537-30-3 syn-2-chloro-7-hydroxynorbornane 
• 38537-30-3 (+/-)-7anti-chloro-norbornane-2exo-ol 
• 21148-26-5 7syn-chloro-norborn-2-ene 
• 13118-70-2 (1R,4S,7R)-Bicyclo[2.2.1]hept-2-en-7-ol 
• 4660-48-4 (+/-)-2exo,7syn-Dichlor-norbornan 
• 21810-44-6 norbornene 

Downstream Products

• 89793-49-7 syn-7-Chlor-nor-campherchinon 
• 24380-97-0 anti-7-Chloro-endo-2-tosyloxybicyclo<2.2.1>heptan 
• 50592-44-4 anti-7-chloro-endo-2-norbornyl brosylate 
• 50592-44-4 anti-7-chloro-exo-2-norbornyl brosylate 

Relevant articles and documents

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Stereochemistry of acid-catalyzed cleavage of 3-chloro- and 3-bromonortricyclene in deuterated medium. Evidence for edge protonation of nortricyclenes

Cleavage of 3-chloronortricyclene (4c) and 3-bromonortricyclene (4d) occurs faster than solvolysis in D2SO4-DOAc at 70-75 deg C and yields syn-7-, anti-7-, exo-5-, and endo-5-halo-exo-2-norbornyl acetates as products.That the 7-chloroacetates comprise 70percent of the reaction mixture, that 30percent of the 5-chloro-exo-2-norbornyl acetates which comprised 28percent of the reaction mixture are derived via rearrangement of the syn-7- and anti-7-chloronorbornyl cations, and that the deuterium at C-6 is at least 90percent stereochemically pure endo is evidence that cleavage of the bond farthest removed from the electron withdrawing halogen is preferred 5:1 over the other bonds of the three-membered ring.The stereochemistry of the ring-opening is rationalized on the basis of cleavage via edge-deuteronation with formation of classical halocations as intermediates.The location of deuterium in the 5-halo-exo-norbornyl acetates is used to define the pathways whereby the 5-haloacetates are formed.This study also establishes that C-6 endo deuterated 7-chloro- and 7-bromo-exo-2-norbornyl brosylates can be synthesized from the corresponding 3-halonortricyclenes.