Pinane

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

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]

References

^ Erman, Mark B.; Kane, Bernard J. (2008). "Chemistry Around Pinene and Pinane: A Facile Synthesis of Cyclobutanes and Oxatricyclo-Derivative of Pinane from cis- and trans-Pinanols". Chemistry & Biodiversity. 5 (6): 910–919. doi:10.1002/cbdv.200890104. PMID 18618388. S2CID 24782774.
^ Eggersdorfer, Manfred (2000). "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205. ISBN 3527306730.
^ Sagorin, Gilles; Cazeils, Emmanuel; Basset, Jean-François; Reiter, Maud (2021). "From Pine to Perfume". CHIMIA. 75 (9): 780–787. doi:10.2533/chimia.2021.780. PMID 34526184.

[1] Erman, Mark B.; Kane, Bernard J. (2008). "Chemistry Around Pinene and Pinane: A Facile Synthesis of Cyclobutanes and Oxatricyclo-Derivative of Pinane from cis- and trans-Pinanols". Chemistry & Biodiversity. 5 (6): 910–919. doi:10.1002/cbdv.200890104. PMID 18618388. S2CID 24782774.

[2] Eggersdorfer, Manfred (2000). "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205. ISBN 3527306730.

[3] Sagorin, Gilles; Cazeils, Emmanuel; Basset, Jean-François; Reiter, Maud (2021). "From Pine to Perfume". CHIMIA. 75 (9): 780–787. doi:10.2533/chimia.2021.780. PMID 34526184.

[1]

[2]

[3]