Cyclohexylmethanol

Cyclohexylmethanol
Names
Preferred IUPAC name
Cyclohexylmethanol
Other names
Cyclohexanemethanol
Identifiers
CAS Number
  • 100-49-2 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 7226
ECHA InfoCard 100.002.598 Edit this at Wikidata
PubChem CID
  • 7507
UNII
  • 4VDR6634UG checkY
CompTox Dashboard (EPA)
  • DTXSID3059212 Edit this at Wikidata
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
  • 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 (66 °F)[1]
Boiling point 187–188 °C (369–370 °F)[3]
Solubility in water
 small in water[4]
Hazards
Flash point 71 °C (160 °F).[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

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

  1. ^ a b c Record of Cyclohexylmethanol in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 4 October 2014..
  2. ^ Prey, Vinzenz; Bartsch, Jürgen (1968). "Dipolmessungen an Pyranose- und Furanose-Modellsubstanzen". Justus Liebigs Annalen der Chemie (in German). 712 (1). Wiley-VCH: 201–207. doi:10.1002/jlac.19687120124.
  3. ^ Rickborn, Bruce; Wood, Stanley E. (1971). "Cleavage of cyclopropanes by diborane". Journal of the American Chemical Society. 93 (16). American Chemical Society: 3940–3946. doi:10.1021/ja00745a021.
  4. ^ Ruelle, Paul; Kesselring, Ulrich W. (February 1997). "The Hydrophobic Propensity of Water toward Amphiprotic Solutes: Predicton and Molecular Origin of the Aqueous Solubility of Aliphatic Alcohols". Journal of Pharmaceutical Sciences. 86 (2). American Pharmacists Association, Elsevier: 179–186. doi:10.1021/js9603109. ISSN 0022-3549.
  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 (1999). "The Unmodified Homogeneous Rhodium-Catalyzed Hydroformylation of Cyclohexene and the Search for Monometallic Catalytic Binuclear Elimination". Organometallics. 18 (8). American Chemical Society: 1542–1546. doi:10.1021/om980531k. ISSN 1520-6041.