765-67-3

Basic information

• Product Name: 1-chlorobicyclo[2.2.1]heptane
• Synonyms: 1-chlorobicyclo[2.2.1]heptane;(4β)-1-Chloronorbornane;1-Chloronorbornane
• CAS NO: 765-67-3
• Molecular Formula: C₇H₁₁Cl
• Molecular Weight: 130.61524
• EINECS: 212-152-7
• Mol File: 765-67-3.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 165.6°C at 760 mmHg
• Flash Point: 39.2°C
• Appearance: /
• Density: 1.09g/cm³
• Vapor Pressure: 2.45mmHg at 25°C
• Refractive Index: 1.501
• CAS DataBase Reference: 1-chlorobicyclo[2.2.1]heptane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-chlorobicyclo[2.2.1]heptane(765-67-3)
• EPA Substance Registry System: 1-chlorobicyclo[2.2.1]heptane(765-67-3)

Safety Data

• Hazardous Substances Data: 765-67-3(Hazardous Substances Data)

Usage

General Description

1-Chlorobicyclo[2.2.1]heptane is a chemical compound with the molecular formula C7H11Cl. It is a bicyclic compound with a chlorine atom attached to one of the carbon atoms in the ring. The compound is also known as norbornyl chloride and is used in organic synthesis and as a starting material for various chemical reactions. It can undergo ring-opening reactions and is used to prepare various derivatives and functionalized compounds. 1-Chlorobicyclo[2.2.1]heptane has a rigid molecular structure due to its bicyclic nature, which makes it useful for controlling the stereochemistry of reactions and as a building block for complex organic molecules. It is important to handle this compound with care, as it is a flammable and toxic substance.

InChI:InChI=1/C7H11Cl/c8-7-3-1-6(5-7)2-4-7/h6H,1-5H2

Upstream product

• 36284-91-0 N-(1-norbornyl)-N',N'-dimethyl-N-nitrosourea 
• 930-80-3 1-iodonorbornane 
• 18720-30-4 Norbornane-1-carboxylic acid 
• 19916-65-5 2,2-dichloronorbornane 
• 93280-54-7 N',N'-dimethyl-N-(1-norbornyl)urea 
• 18720-30-4 norbornane-1-carboxylic acid 
• 497-38-1 Norbornan-2-on 
• 19916-65-5 2,2-dichlorobicyclo<2.2.1>heptane 
• 67-56-1 methanol 
• 433713-11-2 3-(bicyclo[2.2.1]hept-1-yloxy)-3-chloro-3H-diazirine 
• 7446-70-0 aluminium trichloride 
• 109-66-0 pentane 
• 49598-75-6 sodium salt of 1-norbornylnitramine 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 

Downstream Products

• 930-81-4 1-norbornyllithium 
• 1015-14-1 Norborn-1-yl-phenyl-keton 
• 34298-80-1 1-Norbornylaceton 
• 18720-30-4 norbornane-1-carboxylic acid 
• 24892-79-3 1-phenyl-norbornane 
• 61192-21-0 1-(3-methylphenyl)norbornane 
• 61192-22-1 1-p-Tolylnorbornan 
• 62226-67-9 1-(3-fluorophenyl)norbornane 
• 62226-38-4 1-(4-fluorophenyl)norbornane 
• 62226-66-8 1-(2-fluorophenyl)norbornane 

Relevant articles and documents

Lewis acid-catalyzed rearrangement of 2,2-dichloronorbornane to 1-chloronorbornane

The mechanism for the unusual AlCl3-catalyzed rearrangement of 2,2-dichloronorbornane to 1-chloronorbornane in pentane has been elucidated; the reaction, which also yields four isomeric dichloronorbornanes, occurs in three steps: (1) ionization

Single Electron Transfer in Nucleophilic Aliphatic Substitution. Evidence for Single Electron Transfer in the Reactions of 1-Halonorbornanes with Various Nucleophiles

A series of 1-halonorbornanes was used as a model system in reactions with several nucleophiles in order to determine the involvement of single electron transfer (SET) in nucleophilic aliphatic substitution in the absence of light.The 1-halonorbornanes were allowed to react with Me3Sn(1-), Ph2P(1-), AlH4(1-), N(iPr)2(1-), SPh(1-), and the 2-nitropropyl anion in the ether solvents at room temperature to 0 deg C.The results of product analyses, the use of radical and radical anion trapping reagents, the results of deuterium labeling studies, and the nucleofugality effect support a SET mechanism for the reactions involving 1-iodonorbornane.Convincing evidence that reduction of hindered alkyl iodides with LiAlH4 takes place by a SET pathway rather than by an impurity-initiated halogen atom radical chain process followed by an SN2 pathway, is presented.

Synthesis of Bridgehead Halides by Barton Halodecarboxylation

Bridgehead carboxylic acids can be converted into their corresponding chlorides very efficiently under Barton halodecarboxylation conditions.Addition of the acid chloride to a suspension of the sodium salt of 1-hydroxypyridine-2(1H)-thione in boiling carbon tetrachloride under irradiation leads to excellent yields of the bridgehead chloride via the derived thiohydroxamic ester.In a useful modification for the synthesis of volatile halides, either 1,1,1-trichloro-2,2,2-trifluoroethane or trichlorofluoromethane can be employed as substitute solvents.It is found that the Barton procedure is applicable to the synthesis of labile bromides such as 1-bromobicycloheptane for which the usual Hunsdiecker reaction fails.For these, and other brominations, 2-bromo-2-chloro-1,1,1-trifluoroethane ('Halothane') is shown to function as an efficient solvent/bromine atom donor.