Cycloheptanol
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| Names | |
|---|---|
| IUPAC name
Cycloheptanol[1] | |
| Other names | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.007.215 |
| EC Number |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C7H13OH | |
| Molar mass | 114.188 g·mol−1 |
| Appearance | Colorless oily liquid[2][3] |
| Odor | Mild, sweet, alcoholic[4], pleasant[5] |
| Density | 0.948 g/cm3[6] |
| Melting point | 7.15 °C (44.87 °F; 280.30 K)[7] |
| Boiling point | 185 °C (365 °F; 458 K)[6] |
| Practically insoluble[4] | |
| Solubility | High solubility and miscibility with many organic solvents.[4] Chloroform (sparingly), methanol (slightly).[8] |
Refractive index (nD) |
1.48[2] |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H226 | |
| P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, P501 | |
| Flash point | 64 °C (147 °F; 337 K)[6] |
| 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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Cycloheptanol is the organic compound with the chemical formula (CH2)6CHOH or C7H13OH. It is a colorless oily liquid with mild, sweet alcoholic odor. The molecule is related to 7-membered cycloheptane ring in which one of its hydrogen atoms is replaced by a hydroxyl group.
Synthesis
[edit]Cycloheptanol can be synthesized by reduction of cycloheptanone.[9]
Properties
[edit]Cycloheptanol molecule consists of a large nonpolar hydrophobic 7-membered hydrocarbon ring (−C7H13) (which is contributing to cycloheptanol's practical insolubility in water), with a polar hydrophilic hydroxyl group (−OH) attached to it.[4]
Solid cycloheptanol shows polymorphism at low temperatures. Four phases are discovered: phase I, II, III and IV. Phases I and II are orientationally disordered. Phases III and IV are orthorhombic.[10] The phase transition temperatures are: from liquid phase to phase I 7.15 °C (44.87 °F) (melting point), from phase I to phase II −14.70 °C (5.54 °F), from phase II to phase III −45.89 °C (−50.60 °F).[11][12]
Uses
[edit]It is used in organic synthesis, as a solvent and as an intermediate in the production of various chemicals.[5]
Safety
[edit]Cycloheptanol is a flammable chemical, difficult to ignite. Vapors can form explosive mixtures with air on intense heating, and are 3.94 times heavier than air, thus, they may spread along floors.[3][6] It reacts violently with strong oxidising agents and acid anhydrides. When on fire, it emits toxic gases of carbon monoxide and carbon dioxide. Keep away from open flames, hot surfaces and sources of ignition. Precautionary measures against static discharge must be taken.[6]
References
[edit]- 1 2 3 4 PubChem. "Cycloheptanol". pubchem.ncbi.nlm.nih.gov. Retrieved 25 April 2026.
- 1 2 TCI. "Cycloheptanol". www.tcichemicals.com. Retrieved 25 April 2026.
- 1 2 GESTIS. "Cycloheptanol". gestis.dguv.de. Retrieved 25 April 2026.
- 1 2 3 4 BENCHCHEM. "cycloheptanol solubility in water and organic solvents" (PDF). pdf.benchchem.com. Retrieved 25 April 2026.
- 1 2 cymitquimica. "CAS 502-41-0: Cycloheptanol". cymitquimica.com. Retrieved 25 April 2026.
- 1 2 3 4 5 Sigma-Aldrich. "Cycloheptanol". www.sigmaaldrich.com. Retrieved 25 April 2026.
- ↑ Haynes, William M. (4 June 2014). CRC Handbook of Chemistry and Physics. CRC Press. ISBN 978-1-4822-0868-9.
- ↑ Chemical Book. "502-41-0(Cycloheptanol) Product Description". www.chemicalbook.com. Retrieved 25 April 2026.
- ↑ ChemSrc. "Cycloheptanol". www.chemsrc.com. Retrieved 26 April 2026.
- ↑ Salud, J.; López, D. O.; Diez-Berart, S.; Pérez-Jubindo, M. A.; de la Fuente, M. R.; Rute, M. A.; Puertas, R. (2009). "Solid phases in cycloheptanol: Dynamic disorder and glass transitions". Journal of non Crystalline Solids. 355 (52–54): 2550. Bibcode:2009JNCS..355.2550S. doi:10.1016/j.jnoncrysol.2009.09.007.
- ↑ Puertas, R.; Salud, J.; López, D. O.; Rute, M. A.; Diez, S.; Tamarit, J. Ll.; Barrio, M.; Pérez-Jubindo, M. A.; de la Fuente, M. R.; Pardo, L. C. (2005). "Static and dynamic studies on cycloheptanol as two-orientational glass-former". Chemical Physics Letters. 401 (4): 368. Bibcode:2005CPL...401..368P. doi:10.1016/j.cplett.2004.11.078.
- ↑ Adachi, Keiichiro; Suga, Hiroshi; Seki, Syûzô (1972). "Calorimetric Study of the Glassy State. VII. Phase Changes between the Crystalline Phases of Cycloheptanol with Various Degrees of Stability". Bulletin of the Chemical Society of Japan. 45 (7): 1960–1972. doi:10.1246/bcsj.45.1960.