Neopentane

Neopentane, also called 2,2-dimethylpropane, is a double-branched-chain alkane with five carbon atoms, with the chemical formula C(CH3)4. Neopentane is a flammable gas at room temperature and pressure which can condense into a highly volatile liquid on a cold day, in an ice bath, or when compressed to a higher pressure. Neopentane is the simplest alkane with a quaternary carbon, and has achiral tetrahedral symmetry. It is one of the three structural isomers with the molecular formula C5H12 (pentanes), the other two being n-pentane and isopentane. Out of these three, it is the only one to be a gas at standard conditions; the others are liquids. It was first synthesized by Russian chemist Mikhail Lvov in 1870. The traditional name neopentane, coined by William Odling in 1876, was still retained in the 1993 IUPAC recommendations, but is no longer recommended according to the 2013 recommendations. The preferred IUPAC name is the systematic name 2,2-dimethylpropane, but the substituent numbers are superfluous because it is the only possible "dimethylpropane". A neopentyl substituent, often symbolized by "Np", has the structure Me3C–CH2– for instance neopentyl alcohol (Me3CCH2OH or NpOH). As Np also symbolises the element neptunium (atomic number 93), one should use this abbreviation with care.