Cyclooctanol
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| Names | |
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| IUPAC name
Cyclooctanol[1] | |
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 liquid[2][3] |
| Odor | Pleasant[3] |
| Density | 0.974 g/cm3[4] |
| Melting point | 15 °C (59 °F; 288 K)[5] |
| Boiling point | 209 °C (408 °F; 482 K)[2] |
| Slightly[3], 6.576 g/l[5] | |
| Solubility | Soluble in organic solvents such as ethanol and diethyl ether.[3] Miscible with acetone.[6] |
| log P | 2.09160[4] |
| Vapor pressure | 0.1 hPa at 20 °C (68 °F)[5] |
Refractive index (nD) |
1.486[6] |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
May cause serious eye irritation[5] |
| 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) |
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
[edit]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.[4][8]
Properties
[edit]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
[edit]Cyclooctanol reacts with diethylaminosulfur trifluoride to give fluorocyclooctane and cyclooctene.[11]
References
[edit]- 1 2 PubChem. "Cyclooctanol". pubchem.ncbi.nlm.nih.gov. Retrieved 25 April 2026.
- 1 2 3 4 Sigma-Aldrich. "Cyclooctanol for synthesis". www.sigmaaldrich.com. Retrieved 26 April 2026.
- 1 2 3 4 Cymit Química. "CAS 696-71-9: Cyclooctanol". cymitquimica.com. Retrieved 29 April 2026.
- 1 2 3 ChemSrc. "cyclooctanol". www.chemsrc.com. Retrieved 29 April 2026.
- 1 2 3 4 GESTIS. "Cyclooctanol". gestis.dguv.de. Retrieved 30 April 2026.
- 1 2 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.