Cyclohexylmethanol

Cyclohexylmethanol
Names
	Preferred IUPAC name Cyclohexylmethanol
	Other names Cyclohexanemethanol
Identifiers
CAS Number	100-49-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	7226;
ECHA InfoCard	100.002.598
PubChem CID	7507;
UNII	4VDR6634UG ;
CompTox Dashboard (EPA)	DTXSID3059212 ;
	InChI InChI=1S/C7H14O/c8-6-7-4-2-1-3-5-7/h7-8H,1-6H2 Key: VSSAZBXXNIABDN-UHFFFAOYSA-N; InChI=1/C7H14O/c8-6-7-4-2-1-3-5-7/h7-8H,1-6H2 Key: VSSAZBXXNIABDN-UHFFFAOYAW;
	SMILES C1CCC(CC1)CO;
Properties
Chemical formula	C7H14O
Molar mass	114,19 g·mol−1
Appearance	colorless liquid with a smell of alcohol[1]
Density	0,9339 g·cm−3[2]
Melting point	19 °C[1]
Boiling point	187-188 °C[3]
Solubility in water	small in water[4]
Hazards
Flash point	71 °C.[1]
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Cyclohexylmethanol is an organic compound with the formula C₆H₁₁–CH₂–OH. It is a cyclohexane ring functionalized with an alcohol, specifically a hydroxymethyl group. The compound is a colorless liquid, although commercial samples can appear yellow.

Production

Cyclohexylmethanol can be produced in two step starting with the hydroformylation of cyclohexene. This process also give cyclohexane, resulting from hydrogenation. The resulting cyclohexanecarboxaldehyde is then hydrogenated to give the alcohol.[5][6]

References

Record of Cyclohexylmethanol in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 4 October 2014..
Vinzenz Prey, Jürgen Bartsch: Dipolmessungen an Pyranose- und Furanose-Modellsubstanzen. In: Justus Liebigs Annalen der Chemie. 712, 1968, S. 201–207, doi:10.1002/jlac.19687120124.
Bruce Rickborn, Stanley E. Wood: Cleavage of cyclopropanes by diborane. In: Journal of the American Chemical Society. 93, 1971, S. 3940–3946, doi:10.1021/ja00745a021.
Paul Ruelle, Ulrich W. Kesselring: The hydrophobic propensity of water toward amphiprotic solutes: Prediction and molecular origin of the aqueous solubility of aliphatic alcohols. In: Journal of Pharmaceutical Sciences. 86, 1997, S. 179–186, doi:10.1021/js9603109.
EP patent 2000453, Tominaga Kenichi, "Method for Producing Alcohol by Using Carbon Dioxide as Raw MaterialL", published 2008-12-10.
Feng, Jinhai; Garland, Marc. "The Unmodified Homogeneous Rhodium-Catalyzed Hydroformylation of Cyclohexene and the Search for Monometallic Catalytic Binuclear Elimination" Organometallics 1999, volume 18, 1542-1546. doi:10.1021/om980531k

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[GESTIS-1] Record of Cyclohexylmethanol in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 4 October 2014..

[Dipolmessungen-2] Vinzenz Prey, Jürgen Bartsch: Dipolmessungen an Pyranose- und Furanose-Modellsubstanzen. In: Justus Liebigs Annalen der Chemie. 712, 1968, S. 201–207, doi:10.1002/jlac.19687120124.

[3] Bruce Rickborn, Stanley E. Wood: Cleavage of cyclopropanes by diborane. In: Journal of the American Chemical Society. 93, 1971, S. 3940–3946, doi:10.1021/ja00745a021.

[4] Paul Ruelle, Ulrich W. Kesselring: The hydrophobic propensity of water toward amphiprotic solutes: Prediction and molecular origin of the aqueous solubility of aliphatic alcohols. In: Journal of Pharmaceutical Sciences. 86, 1997, S. 179–186, doi:10.1021/js9603109.

[5] EP patent 2000453, Tominaga Kenichi, "Method for Producing Alcohol by Using Carbon Dioxide as Raw MaterialL", published 2008-12-10.

[6] Feng, Jinhai; Garland, Marc. "The Unmodified Homogeneous Rhodium-Catalyzed Hydroformylation of Cyclohexene and the Search for Monometallic Catalytic Binuclear Elimination" Organometallics 1999, volume 18, 1542-1546. doi:10.1021/om980531k