Cyclopropanol

Cyclopropanol
IUPAC name

Cyclopropanol
Other names

Cyclopropyl alcohol, Hydroxycyclopropane
Identifiers
CAS number 16545-68-9
PubChem 123361
ChemSpider 109961 Y
Jmol-3D images Image 1
Properties
Molecular formula C3H6O
Molar mass 58.08 g mol−1
Density 0.917 g/mL[1]
Boiling point

101–102 °C[2]
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.[3][4] 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[5] and of modulators of protein trafficking.[6]

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