10464-71-8

Basic information

• Product Name: Bicyclo[2.2.1]heptan-2-one,3-chloro-, (1R,3R,4S)-rel-
• Synonyms: 2-Norbornanone,3-chloro-, exo- (8CI); Bicyclo[2.2.1]heptan-2-one, 3-chloro-, exo-; (?à)-exo-3-Chloro-2-norbornanone; NSC 176866; exo-3-Chlorobicyclo[2.2.1]heptan-2-one; exo-3-Chloronorbornan-2-one; exo-Chloronorcamphor
• CAS NO: 10464-71-8
• Molecular Formula: C₇H₉ClO
• Molecular Weight: 144.5988
• Mol File: 10464-71-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 225.6°Cat760mmHg
• Flash Point: 94.4°C
• Density: 1.23g/cm³
• CAS DataBase Reference: Bicyclo[2.2.1]heptan-2-one,3-chloro-, (1R,3R,4S)-rel-(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[2.2.1]heptan-2-one,3-chloro-, (1R,3R,4S)-rel-(10464-71-8)
• EPA Substance Registry System: Bicyclo[2.2.1]heptan-2-one,3-chloro-, (1R,3R,4S)-rel-(10464-71-8)

Safety Data

• Hazardous Substances Data: 10464-71-8(Hazardous Substances Data)

Upstream product

• 498-66-8 norbornene 
• 497-38-1 Norbornan-2-on 
• 498-66-8 norborn-2-ene 
• 497-38-1 2-norbornanone 
• 66057-08-7 ((1R,4S)-3-Chloro-bicyclo[2.2.1]hept-2-en-2-yloxy)-trimethyl-silane 
• 4321-46-4 endo-2-chloro-exo-3-hydroxybicyclo<2.2.1>heptane 
• 10464-71-8 exo-3-chlorobicyclo<2.2.1>heptan-2-one 
• 109-89-7 diethylamine 
• 66057-08-7 (3-Chloro-bicyclo[2.2.1]hept-2-en-2-yloxy)-trimethyl-silane 
• 75819-75-9 endo-3-chloro-exo-2-norbornyl tert-butyl ether 

Downstream Products

• 10464-71-8 endo-3-chloro-2-norbornanone 
• 94225-33-9 2-((1S,2R,3S,4R)-3-Chloro-2-hydroxy-bicyclo[2.2.1]hept-2-yl)-1-phenyl-ethanone 

Relevant articles and documents

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OXIDATION OF OLEFINS USING CHROMIC ANHYDRIDE-CHLOROTRIMETHYLSILANE. A CONVENIENT SYNTHESIS OF α-CHLORO KETONES.

Disubstituted internal olefins are oxidized selectively to α-chloro ketones in excellent yields from the reaction with chromic anhydride-chlorotrimethylsilane in carbon tetrachloride.

Towards a complete account of the mechanism of hydrogen isotope exchange of diastereotopic protons of carbon acids. II. Acid- and base-catalyzed enolization of bicyclohepten-2-ones. Evidence for exchange by inversion

A study of acid- and base-catalyzed hydrogen isotope exchange of bicycloheptan-2-one (1a) and its 3-deuteriated analogs has been carried out.We find that the kexo/kendo ratio (658+/-66) for deuteroxide-catalyzed H * D exchange of 1a at C-3 is 7.2 +/- 1.5 times greater than the kexo/kendo ratio (91 +/- 9) for hydroxide catalyzed D * H exchange of 1b.For acid-catalyzed exchange in CH3COOD(H)-D(H)Cl the rate ratios are 156 +/- 20 and 29 +/- 2 for H * D and D * H exchange, respectively.Equations which relate the observed selectivity kexo/kendo (kfast/kslow) to the intrinsic selectivity and the primary, secondary, and solvent KIEs are developed.The differences between the rate ratios for H * D and D * H exchange are interpreted on the basis of a significant contribution of an inversion pathway to exchange of the slow proton (deuteron).The significance of our study - it relates to the mechanism of hydrogen isotope exchange of diastereotopic protons (deuterons, tritons) of any carbon acid - is discussed.