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Cyclopropanol

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Cyclopropanol
Names
Preferred IUPAC name Cyclopropanol
Other names Cyclopropyl alcohol, Hydroxycyclopropane
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.217.724 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H6O/c4-3-1-2-3/h3-4H,1-2H2Key: YOXHCYXIAVIFCZ-UHFFFAOYSA-N
SMILES
  • OC1CC1
Properties
Chemical formula C3H6O
Molar mass 58.080 g·mol
Density 0.917 g/mL
Boiling point 101 to 102 °C (214 to 216 °F; 374 to 375 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Cyclopropanol is an organic compound with the chemical formula C3H6O. It contains a cyclopropyl group with a hydroxyl group attached to it. The compound is highly unstable due to the three-membered ring, and is susceptible to reactions that open the ring. It is highly prone to rearrangement, undergoing structural isomerization to form propanal. This property is useful synthetically: cyclopropanol can be used as a synthon for the homoenolate of propanal. The chemical is also useful as a reagent to introduce a cyclopropyl group into ester, sulfate, and amine linkages. The resulting cyclopropyl-containing compounds have been used in investigations of potential antiviral drugs and of modulators of protein trafficking.

References

  1. Roberts, J. D.; Chambers, V. C. (1951). "Small-Ring Compounds. VI. Cyclopropanol, Cyclopropyl Bromide and Cyclopropylamine". J. Am. Chem. Soc. 73 (7): 3176–3179. doi:10.1021/ja01151a053.
  2. Jongejan, J. A.; Duine, J. A. (1987). "Enzymatic hydrolysis of cyclopropyl acetate. A facile method for medium- and large-scale preparations of cyclopropanol". Tetrahedron Lett. 28 (24): 2767–2768. doi:10.1016/S0040-4039(00)96204-X.
  3. Magrane, J. K.; Cottle, D. L. (1942). "The Reaction of Epichlorohydrin with the Grignard Reagent". J. Am. Chem. Soc. 64 (3): 484–487. doi:10.1021/ja01255a004.
  4. Stahl, G. W.; Cottle, D. L. (1943). "The Reaction of Epichlorohydrin with the Grignard Reagent. Some Derivatives of Cyclopropanol". J. Am. Chem. Soc. 65 (9): 1782–1783. doi:10.1021/ja01249a507.
  5. WO application 2009005677, Cottell, J. J.; Link, J. O. Schroeder, S. D.; Taylor, J.; Tse, W.; Vivian, R. W.; Yang, Z.-Y., "Antiviral compounds", published 2009-01-08 
  6. WO application 2009062118, Bulawa, C. E.; Devit, M.; Elbaum, D., "Modulators of protein trafficking", published 2009-05-14 
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