765-91-3

Basic information

• Product Name: EXO-2-CHLORONORBORNANE
• Synonyms: EXO-2-CHLORONORBORNANE;2-Chlorobicyclo[2.2.1]heptane;exo-2-Norbornyl chloride;exo-Norbornyl chloride;Norbornane, 2-chloro-, exo-;Bicyclo(2.2.1)heptane, 2-chloro-, exo-
• CAS NO: 765-91-3
• Molecular Formula: C₇H₁₁Cl
• Molecular Weight: 130.62
• Product Categories: Alkyl;Halogenated Hydrocarbons;Organic Building Blocks;Building Blocks;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 765-91-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: -5 °C
• Boiling Point: 66-66.5 °C30 mm Hg(lit.)
• Flash Point: 112 °F
• Appearance: /
• Density: 1.06 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.29mmHg at 25°C
• Refractive Index: n20/D 1.4854(lit.)
• CAS DataBase Reference: EXO-2-CHLORONORBORNANE(CAS DataBase Reference)
• NIST Chemistry Reference: EXO-2-CHLORONORBORNANE(765-91-3)
• EPA Substance Registry System: EXO-2-CHLORONORBORNANE(765-91-3)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 765-91-3(Hazardous Substances Data)

Usage

Uses

exo-2-Chloronorbornane has been employed as reagent during Friedel-Crafts alkylation of benzene and substituted benzenes with tin(IV) chloride or aluminium trichloride.

General Description

exo-2-Chloronorbornane undergoes amination with trichloramine-aluminum chloride to yield 2-azabicyclo[3.2.1]octane, small amounts of the 3-isomer and exo-2-aminonorbornane.

InChI:InChI=1/C7H11Cl/c8-7-4-5-1-2-6(7)3-5/h5-7H,1-4H2

Upstream product

• 497-38-1 Norbornan-2-on 
• 279-23-2 norbornene 

Downstream Products

• 2534-77-2 exo-2-bromonorbornane 
• 2534-77-2 (+/-)-endo-2-bromonorbornane 
• 279-23-2 norbornene 
• 208707-98-6 2endo-Methoxycarbonyl-norbornan 
• 16646-41-6 exo-2-(methoxycarbonyl)norbornane 

Relevant articles and documents

The 2-norbornyl cation via the fragmentations of exo- and endo-2-norbornyloxychlorocarbenes: Distinction without much difference

exo- and endo-2-norbornyloxychlorocarbenes (7) were generated photochemically from the corresponding diazirines (6). Both carbenes fragmented to [2-norbornyl cation (carbon monoxide) chloride] ion pairs in MeCN or 1,2-dichloroethane solutions. Products included exo-norbornyl chloride (8), endo-norbornyl chloride (9), norbornene (10), and nortricyclene (11). Fragmentation activation energies were very low (5 s-1 in MeCN). Due to chloride return within the ion pairs, product distributions from exo- and endo-7 differed, with more endo-chloride formed from the endo-carbene: the 8/9 product ratio in MeCN was ～41 from exo-7, but only 4.6 from endo-7. Norbornene, formed by proton transfer to Cl- within the ion pairs, was a major product in both cases (44% from exo-7 and 62% from endo-7). In MeOH/MeCN, up to 28% of exo-2-norbornyl methyl ether formed at the expense of some of the norbornene, but even in 100% MeOH, the norbornyl chloride products of ion pair return still accounted for 46% and 31% of the exo-7 and endo-7 product mixtures (accompanied by 26-32% of norbornene). Electronic structure calculations on the ground states and fragmentation transition states of exo-7 and endo-7 are presented.

Kinetics of Ozonation. 6. Polycyclic Aliphatic Hydrocarbons.

The reaction of ozone with norbornane, adamantane and bicyclooctane has been studied, including kinetics and product studies as well as the determination of activation paprameters for the ozonation of norbornane.This work was carried out to distinguish between hydride abstraction and a concerted insertion mechanism for the ozonation of C-H bonds.Kinetically, norbornane behaves like a secondary hydrocarbon and lacks the rate acceleration expected if a carbocation intermediate were involved in a hydride abstraction mechanism.We interpret this and other results as supporting a 1,3-dipolar insertion mechanism for the reaction of ozone with C-H bonds.