Pinane

Pinane describes a pair of isomeric hydrocarbons. The isomers, actually diastereomers, are both chiral. They are the cis and trans isomers arising from the hydrogenation of the terpenes pinene. Both isomers undergo reaction with air (autoxidation) to give 2-pinane hydroperoxides.^[1] Partial reduction of these isomers gives 2-pinanol.^[2] Pyrolysis of pinane gives dimethyloctadienes.^[3]

Formation of dimethyloctadienes

Pinane

Identifiers
CAS Number	473-55-2 cis and trans trans: 6876-13-7 cis: 4755-33-3
3D model (JSmol)	Interactive image trans: Interactive image cis: Interactive image
Beilstein Reference	1847301
ChEBI	CHEBI:35710
ChEMBL	ChEMBL1422299
ChemSpider	9724
ECHA InfoCard	100.006.790
EC Number	207-467-1 trans: 229-978-9
PubChem CID	10129 trans: 6429433 cis: 10969850
UNII	trans: 6603788013 cis: N7C9IBU49F
UN number	3295
CompTox Dashboard (EPA)	DTXSID7025922
InChI InChI=1S/C10H18/c1-7-4-5-8-6-9(7)10(8,2)3/h7-9H,4-6H2,1-3H3 Key: XOKSLPVRUOBDEW-UHFFFAOYSA-N trans: InChI=1S/C10H18/c1-7-4-5-8-6-9(7)10(8,2)3/h7-9H,4-6H2,1-3H3/t7-,8-,9-/m0/s1 Key: XOKSLPVRUOBDEW-CIUDSAMLSA-N cis: InChI=1S/C10H18/c1-7-4-5-8-6-9(7)10(8,2)3/h7-9H,4-6H2,1-3H3/t7-,8+,9+/m1/s1 Key: XOKSLPVRUOBDEW-VGMNWLOBSA-N
SMILES CC1CCC2CC1C2(C)C trans: C[C@H]1CC[C@H]2C[C@@H]1C2(C)C cis: C[C@@H]1CC[C@H]2C[C@@H]1C2(C)C
Properties
Chemical formula	C10H18
Molar mass	138.254 g·mol−1
Appearance	colorless liquids
Boiling point	167.2 – 168 °C (cis) 164 °C (trans)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references