Norbornane Chemical Properties

Melting point:

85-88 °C (lit.)

Boiling point:

106 °C

Density 

0.914±0.06 g/cm3 (20 ºC 760 Torr)

refractive index 

1.4770 (estimate)

Flash point:

-0.2±11.7℃

storage temp. 

2-8°C

solubility 

soluble in Acetone

form 

powder to crystal

color 

White to Almost white

EPA Substance Registry System

Bicyclo[2.2.1]heptane (279-23-2)

Safety Information

WGK Germany 

3

RTECS 

RB6945000

HS Code 

2902.19.0050

Toxicity

mouse,LD50,intravenous,56mg/kg (56mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04038,

MSDS

• Language:English Provider:SigmaAldrich

Norbornane Usage And Synthesis

Description

Norbornane (also known as bicyclo[2.2.1]heptane or norcamphane) is an organic compound and a saturated hydrocarbon with chemical formula C7H12. It is a crystalline compound with a melting point of 88 °C. The carbon skeleton is derived from cyclohexane ring with a methylene bridge in the 1,4- position, and is a bridged bicyclic compound. The compound is a prototype of a class of strained bicyclic hydrocarbons.

Chemical Properties

Norbornane, also known as bicyclo[2.2.1]heptane and norbornane, is a saturated, bridged-ring compound with the chemical formula C7H12.It is a crystalline substance with a melting point of 88°C. It has a carbon skeleton with a methylidene at the 1,4 position. It is formed by bridging a methylene group at positions 1,4 of the carbon skeleton of cyclohexane. Northene is the parent compound of various terpenes such as camphor and anise. This substance can be prepared by catalytic hydrogenation of the related compounds norbornene and norbornadiene. The norbornene-based carbon positive ion (C7H11+) is an attractive non-classical carbon positive ion.

Definition

ChEBI: Norbornane is a cyclic hydrocarbon consisting of cyclohexane with a methylene bridge linking positions 1 and 4. It is a bridged compound and a cyclic hydrocarbon.

Preparation

Norbornane is obtained by adding ethylene to cyclopentadiene under heat and pressure and then hydrogenating.

References

[1] G BUCHBAUER C C S Esterer. [Norbornane compounds in pharmaceutical research].[J]. Pharmazie, 1983, 38 3: 151-169.
[2] CAIFENG LI. Norbornene in Organic Synthesis[J]. Synthesis-Stuttgart, 2018, 15 1: 2799-2823. DOI:10.1055/s-0037-1610143.
[3] KUMAR S, ABDULHAMID M A, WONANKE A D D, et al. Norbornane-based covalent organic frameworks for gas separation?[J]. Nanoscale, 2022, 6: 2475-2481. DOI:10.1039/D1NR07593D.

Norbornane(279-23-2)Related Product Information

• NORCAMPHOR
• 2,3-NORBORNANEDICARBOXYLIC ACID
• norbornane-2-carboxylic acid, predominantly endo,NORBORNANE-2-CARBOXYLIC ACID,NORBORNANE-2-CARBOXYLIC ACID, 98%, PREDOMINANTLY ENDO ISOMER
• 5-Norbornane-2-carboxaldehyde
• 5-Norbornene-2-carbonitrile
• Bicyclo[1.1.1]pentane-1-carboxamide
• Bicyclo[1.1.1]pentane-1,3-dicarboxamide
• Bicyclo[1.1.1]pentane-1-sulfonamide
• bicyclo[1.1.1]pentane-1,3-dicarbonitrile
• 4-Carboxylbenzocyclobutene
• 4-Hydroxymethylbenzocyclobutene
• 4-Aminobenzocyclobutene
• Bicyclo[1.1.1]pentane-1-carboxylic acid, methyl ester (9CI)
• Bicyclo[3.1.0]hexan-3-ol
• bicyclo[3.2.1]octane-2,4-dione
• 5-Norbornene-2-carboxamide
• ETHYL 5-NORBORNENE-2-CARBOXYLATE (MIXTURE OF ENDO AND EXO)
• Bicyclo[2.2.2]octane-1,4-dimethanol