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| Names | |
|---|---|
| IUPAC name
Cyclooctanol1
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Other names
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.010.729 |
| EC Number |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C8H15OH | |
| Molar mass | 128.215 g·mol−1 |
| Appearance | Colorless viscous liquid23 |
| Odor | Pleasant3 |
| Density | 0.974 g/cm34 |
| Melting point | 15 °C (59 °F; 288 K)5 |
| Boiling point | 209 °C (408 °F; 482 K)2 |
| Slightly3, 6.576 g/l5 | |
| Solubility | Soluble in organic solvents such as ethanol and diethyl ether.3 Miscible with acetone.6 |
| log P | 2.091604 |
| Vapor pressure | 0.1 hPa at 20 °C (68 °F)5 |
Refractive index (nD)
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1.4866 |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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May cause serious eye irritation5 |
| GHS labelling: | |
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| 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)2 |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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735 mg/kg (oral, rat)2 |
| Related compounds | |
Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.7
- 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.48
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.9
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.10
Reactions
Cyclooctanol reacts with diethylaminosulfur trifluoride to give fluorocyclooctane and cyclooctene.11
References
References
- PubChem. "Cyclooctanol". pubchem.ncbi.nlm.nih.gov. Retrieved 25 April 2026.
- Sigma-Aldrich. "Cyclooctanol for synthesis". www.sigmaaldrich.com. Retrieved 26 April 2026.
- Cymit Química. "CAS 696-71-9: Cyclooctanol". cymitquimica.com. Retrieved 29 April 2026.
- ChemSrc. "cyclooctanol". www.chemsrc.com. Retrieved 29 April 2026.
- GESTIS. "Cyclooctanol". gestis.dguv.de. Retrieved 30 April 2026.
- ThermoFisher. "Cyclooctanol, 97%". www.thermofisher.com. Retrieved 29 April 2026.
- 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.
- 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.
- 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.
- 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.
- 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.