Norbornane (also known as bicyclo .2.1eptane) is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

and a saturated

hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and Hydrophobe, hydrophobic; their odor is usually fain ...

with

chemical formula A chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as pare ...

C₇H₁₂. It is a

crystalline A crystal or crystalline solid is a solid material whose constituents (such as atoms, molecules, or ions) are arranged in a highly ordered microscopic structure, forming a crystal lattice that extends in all directions. In addition, macrosc ...

compound with a

melting point The melting point (or, rarely, liquefaction point) of a substance is the temperature at which it changes state of matter, state from solid to liquid. At the melting point the solid and liquid phase (matter), phase exist in Thermodynamic equilib ...

of 88

°C The degree Celsius is the unit of temperature on the Celsius temperature scale "Celsius temperature scale, also called centigrade temperature scale, scale based on 0 ° for the melting point of water and 100 ° for the boiling point ...

. The carbon skeleton is derived from

cyclohexane Cyclohexane is a cycloalkane with the molecular formula . Cyclohexane is non-polar. Cyclohexane is a colourless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohexan ...

ring with a

methylene bridge In chemistry, a methylene bridge is part of a molecule with formula . The carbon atom is connected by single bonds to two other distinct atoms in the rest of the molecule. A methylene bridge is often called a methylene group or simply methylene, ...

in the 1,4- position, and is a bridged

bicyclic A bicyclic molecule () is a molecule that features two joined rings. Bicyclic structures occur widely, for example in many biologically important molecules like α-thujene and camphor. A bicyclic compound can be carbocyclic (all of the ring ...

compound. The compound is a prototype of a class of strained bicyclic hydrocarbons. The compound was originally synthesized by reduction of

norcamphor Norcamphor is an organic compound, classified as a bicyclic ketone. It is an structural analog, analog of camphor, but without the three methyl groups. A colorless solid, it is used as a building block in organic synthesis. Norcamphor is prepare ...

. The name norbornane is derived from

bornane Bornane (or camphane) is a compound closely related to norbornane. Its name refers to Borneo, habitat of the tree ''Cinnamomum camphora'' from which bornane and related compounds can be extracted. See also * Camphor Camphor () is a waxy, c ...

, which is 1,7,7-trimethylnorbornane, being a derivative of

camphor Camphor () is a waxy, colorless solid with a strong aroma. It is classified as a terpenoid and a cyclic ketone. It is found in the wood of the camphor laurel (''Cinnamomum camphora''), a large evergreen tree found in East Asia; and in the kapu ...

(bornanone). The prefix ''nor'' refers to the stripping of the methyl groups from the parent molecule bornane.

References

{{Reflist

External links

Norbornane in 3D

Datasheet at ''Sigma-Aldrich''
Bicycloalkanes