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 Edit this at Wikidata
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 Edit this at Wikidata
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
  • 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
Chemical compound

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

  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.