The term may refer to any of three structural isomers, or to a mixture of them: in the IUPAC nomenclature, however, pentane means exclusively the n-pentane isomer, in which case pentanes refers to a mixture of them; the other two are called isopentane (methylbutane) and neopentane (dimethylpropane).
Normal pentane was discovered in 1862 by Carl Schorlemmer, who, while analyzing pyrolysis products of the cannel coal mined in Wigan, identified, separated by fractional distillation and studied a series of liquid hydrocarbons inert to nitric and sulfuric acids.
[11] Pentanes are relatively inexpensive and are the most volatile liquid alkanes at room temperature, so they are often used in the laboratory as solvents that can be conveniently and rapidly evaporated.
As is the case for other alkanes, the more thickly branched isomers tend to have lower boiling points.
[13][14] Rotation about two central single C-C bonds of n-pentane produces four different conformations.
[15] Like other alkanes, pentanes are largely unreactive at standard room temperature and conditions - however, with sufficient activation energy (e.g., an open flame), they readily oxidize to form carbon dioxide and water: Like other alkanes, pentanes undergo free radical chlorination: Without zeolite catalysts, such reactions are unselective, so with n-pentane, the result is a mixture of the 1-, 2-, and 3-chloropentanes, as well as more highly chlorinated derivatives.
[17] Pentane is a relatively minor component of automobile gasoline, with its share varying within 1–6% in 1990s Sweden,[18] 2–13% in 1990s US[19] and 1–3% in the US in 2011.