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 is a set of isomeric terpenes. Existing as chiral cis and trans isomers, they arise from the hydrogenation of pinene. Both isomers undergo reaction with air to give 2-pinane hydroperoxides, also with chiral cis and trans isomers.^[1] Partial reduction of these isomers gives 2-pinanol.^[2]

References[edit]

^ 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 978-3527306732.

[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 978-3527306732.

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