Cyclooctanol

Cyclooctanol
Cyclooctanol structural formula
Names
IUPAC name
Cyclooctanol
Other names
  • Cyclooctyl alcohol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.010.729 Edit this at Wikidata
EC Number
  • 211-800-6
UNII
  • InChI=1S/C8H16O/c9-8-6-4-2-1-3-5-7-8/h8-9H,1-7H2
    Key: FHADSMKORVFYOS-UHFFFAOYSA-N
  • C1CCCCCCC1O
Properties
C8H15OH
Molar mass 128.215 g·mol−1
Appearance Colorless viscous liquid
Odor Pleasant
Density 0.974 g/cm3
Melting point 15 °C (59 °F; 288 K)
Boiling point 209 °C (408 °F; 482 K)
Slightly, 6.576 g/l
Solubility Soluble in organic solvents such as ethanol and diethyl ether. Miscible with acetone.
log P 2.09160
Vapor pressure 0.1 hPa at 20 °C (68 °F)
1.486
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 May cause serious eye irritation
GHS labelling:
GHS07: Exclamation mark
Warning
H227, H302, H315, H319, H335
P210, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403, P403+P233, P405, P501
Flash point 86 °C (187 °F; 359 K)
Lethal dose or concentration (LD, LC):
735 mg/kg (oral, rat)
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cyclooctanol is an organic compound with the formula (CH2)7CHOH or C8H15OH. It is a colorless oily liquid with a pleasant odor. The molecule consists of 8-membered cyclooctane ring in which one of its hydrogen atoms is replaced by a hydroxyl group.

Synthesis

Cyclooctanol can be obtained by hydrolysis of cyclooctyl formate.

HCOOC8H15 + H2O → C8H15OH + HCOOH

Cyclooctanol can also be synthesized by oxidation of cyclooctane by hydrogen peroxide with polyoxometalates as catalysts in acetonitrile. The reaction byproducts are cyclooctanone and cyclooctyl hydroperoxide.

Properties

It has been investigated how cyclooctanol behaves under high pressure. At around 0.4 GPa cyclooctanol becomes a solid, which is in the form of plastic crystals. At around 1.1 GPa, it becomes a normal ordered crystal phase. These phase transitions are reversible.

Under high pressure, new solid phase of cyclooctanol (phase III) is discovered and characterized as a normal crystal phase, and all other solid phases (I, II, IV) are characterized as plastic crystal phases.

Reactions

Cyclooctanol reacts with diethylaminosulfur trifluoride to give fluorocyclooctane and cyclooctene.

References

  1. 1 2 PubChem. "Cyclooctanol". pubchem.ncbi.nlm.nih.gov. Retrieved 25 April 2026.
  2. 1 2 3 4 Sigma-Aldrich. "Cyclooctanol for synthesis". www.sigmaaldrich.com. Retrieved 26 April 2026.
  3. 1 2 3 4 Cymit Química. "CAS 696-71-9: Cyclooctanol". cymitquimica.com. Retrieved 29 April 2026.
  4. 1 2 3 ChemSrc. "cyclooctanol". www.chemsrc.com. Retrieved 29 April 2026.
  5. 1 2 3 4 GESTIS. "Cyclooctanol". gestis.dguv.de. Retrieved 30 April 2026.
  6. 1 2 ThermoFisher. "Cyclooctanol, 97%". www.thermofisher.com. Retrieved 29 April 2026.
  7. ↑ Sommer, Tomáš; Zapletal, Martin; Trejbal, Jiří (2018). "Production of cyclic alcohols". Chemical Papers. 72 (10): 2397–2412. Bibcode:2018ChPap..72.2397S. doi:10.1007/s11696-018-0508-5.
  8. ↑ Wimonrat, Trakarnpruk; Apiwat, Wannatem; Jutatip, Kongpeth (January 1, 2012). "Polyoxometalates catalysts in the oxidation of cyclooctane by hydrogen peroxide" (PDF). Journal of the Serbian Chemical Society. 77 (11): 1599–1607. doi:10.2298/jsc111124040t – via doaj.org.
  9. ↑ Ren, Yufen; Cheng, Xuerui; Yang, Kun; Zhu, Xiang; Li, Haining; Wang, Yongqiang (December 15, 2015). "Raman study of plastic crystal phase of cyclooctanol under high pressure with different compression rate". Journal of Molecular Structure. 1102: 6–10. Bibcode:2015JMoSt1102....6R. doi:10.1016/j.molstruc.2015.08.006 – via ScienceDirect.
  10. ↑ Andersson, Ove; Ross, Russell G. (1990). "Thermal conductivity, heat capacity and phase diagram of cyclooctanol in liquid, solid and glassy crystal states under high pressure". Molecular Physics. 71 (3): 523–539. Bibcode:1990MolPh..71..523A. doi:10.1080/00268979000101951.
  11. ↑ Middleton, William J. (1975). "New fluorinating reagents. Dialkylaminosulfur fluorides". The Journal of Organic Chemistry. 40 (5): 574–578. Bibcode:1975JOrgC..40..574M. doi:10.1021/jo00893a007.