Cyclooctanol
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| IUPAC name
Cyclooctanol[1]
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Other names
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). |
| E number | Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C 8H 15OH | |
| 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)
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1.486[6] |
| Hazards | |
| Main hazards | May cause serious eye irritation[5] |
| GHS pictograms | 
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| GHS Signal word | |
| <abbr class="abbr" title="Error in hazard statements">HH227, <abbr class="abbr" title="Error in hazard statements">HH302, <abbr class="abbr" title="Error in hazard statements">HH315, <abbr class="abbr" title="Error in hazard statements">HH319, <abbr class="abbr" title="Error in hazard statements">HH335 | |
| <abbr class="abbr" title="Error in hazard statements">PP210, <abbr class="abbr" title="Error in hazard statements">PP261, <abbr class="abbr" title="Error in hazard statements">PP264, <abbr class="abbr" title="Error in hazard statements">PP264+P265, <abbr class="abbr" title="Error in hazard statements">PP270, <abbr class="abbr" title="Error in hazard statements">PP271, <abbr class="abbr" title="Error in hazard statements">PP280, <abbr class="abbr" title="Error in hazard statements">PP301+P317, <abbr class="abbr" title="Error in hazard statements">PP302+P352, <abbr class="abbr" title="Error in hazard statements">PP304+P340, <abbr class="abbr" title="Error in hazard statements">PP305+P351+P338, <abbr class="abbr" title="Error in hazard statements">PP319, <abbr class="abbr" title="Error in hazard statements">PP321, <abbr class="abbr" title="Error in hazard statements">PP330, <abbr class="abbr" title="Error in hazard statements">PP332+P317, <abbr class="abbr" title="Error in hazard statements">PP337+P317, <abbr class="abbr" title="Error in hazard statements">PP362+P364, <abbr class="abbr" title="Error in hazard statements">PP370+P378, <abbr class="abbr" title="Error in hazard statements">PP403, <abbr class="abbr" title="Error in hazard statements">PP403+P233, <abbr class="abbr" title="Error in hazard statements">PP405, <abbr class="abbr" title="Error in hazard statements">PP501 | |
| 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). | |
| Infobox references | |
Cyclooctanol is an organic compound with the formula (CH
2)
7CHOH or C
8H
15OH. It is a colorless oily liquid with a pleasant odor. The molecule is related to 8-membered cyclooctane ring in which one of its hydrogen atoms is replaced by a hydroxyl group.
Synthesis
It can be obtained by hydrolysis of cyclooctyl formate[7] or by oxidation of cyclooctane.[4]
Properties
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.[8]
Its chemical properties include the ability to undergo typical alcohol reactions, such as esterification and oxidation, making it versatile in various chemical processes.[3]
Uses
Cyclooctanol is used as a solvent and as an intermediate in organic synthesis, especially in the production of various chemical compounds. Additionally, it has applications in the fragrance industry due to its pleasant odor.[3] It is a starting chemical used for the synthesis of cylooctanone by using a chromic acid reagent as an oxidizing agent.[6]
Reactions
Cyclooctanol reacts with diethylaminosulfur trifluoride to give fluorocyclooctane and cyclooctene.[9]
Safety
Cyclooctanol is difficult to ignite.[5] Its vapors are heavier than air and may spread along floors. Forms explosive mixtures with air on intense heating.[2] While it may cause irritation upon contact with skin and eyes, it is generally considered to have low toxicity.[3] May cause irritations of mucous membranes in the mouth, pharynx, oesophagus and gastrointestinal tract. Violent chemical reactions are possible with strong oxidizing agents, acid halides and acid anhydrides.[2]
References
- ↑ 1.0 1.1 PubChem. "Cyclooctanol". pubchem.ncbi.nlm.nih.gov. Retrieved 25 April 2026.
- ↑ 2.0 2.1 2.2 2.3 2.4 2.5 Sigma-Aldrich. "Cyclooctanol for synthesis". www.sigmaaldrich.com. Retrieved 26 April 2026.
- ↑ 3.0 3.1 3.2 3.3 3.4 3.5 3.6 Cymit Química. "CAS 696-71-9: Cyclooctanol". cymitquimica.com. Retrieved 29 April 2026.
- ↑ 4.0 4.1 4.2 ChemSrc. "cyclooctanol". www.chemsrc.com. Retrieved 29 April 2026.
- ↑ 5.0 5.1 5.2 5.3 5.4 GESTIS. "Cyclooctanol". gestis.dguv.de. Retrieved 30 April 2026.
- ↑ 6.0 6.1 6.2 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.
- ↑ 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.
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