Cyclopropanol

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title: "Cyclopropanol" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["cycloalkanols", "cyclopropyl-compounds"] topic_path: "general/cycloalkanols" source: "https://en.wikipedia.org/wiki/Cyclopropanol" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Watchedfields = changed | verifiedrevid = 441485086 | Name = | ImageFile = Cyclopropanol.svg | ImageSize = 100px | ImageAlt = | ImageName = | PIN = Cyclopropanol | OtherNames = Cyclopropyl alcohol, Hydroxycyclopropane |Section1={{Chembox Identifiers | 3DMet = | Abbreviations = | Beilstein = | CASNo_Ref = | CASNo = 16545-68-9 | CASNoOther = | ChEBI_Ref = | ChEBI = | ChemSpiderID_Ref = | ChemSpiderID = 109961 | DrugBank_Ref = | DrugBank = | EC_number = | EINECS = | Gmelin = | StdInChI_Ref = | StdInChI = 1S/C3H6O/c4-3-1-2-3/h3-4H,1-2H2 | StdInChIKey_Ref = | StdInChIKey = YOXHCYXIAVIFCZ-UHFFFAOYSA-N | KEGG_Ref = | KEGG = | MeSHName = | PubChem = 123361 | RTECS = | SMILES = OC1CC1 | UNNumber = |Section2={{Chembox Properties | AtmosphericOHRateConstant = | Appearance = | BoilingPtC = 101 to 102 | BoilingPt_ref = | BoilingPt_notes = | Density = 0.917 g/mL | C=3 | H=6 | O=1 | HenryConstant = | LogP = | MeltingPt_notes = | pKa = | pKb = | Solubility = | SolubleOther = | Solvent = | VaporPressure =}} |Section3={{Chembox Structure | Coordination = | CrystalStruct = | MolShape = }} |Section4={{Chembox Thermochemistry | DeltaHc = | DeltaHf = | Entropy = | HeatCapacity = }} |Section8={{Chembox Related | OtherFunction_label = | OtherAnions = | OtherCations = | OtherCompounds = | OtherFunction =

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

References

  1. (1987). "Enzymatic hydrolysis of cyclopropyl acetate. A facile method for medium- and large-scale preparations of cyclopropanol". Tetrahedron Lett..
  2. (1951). "Small-Ring Compounds. VI. Cyclopropanol, Cyclopropyl Bromide and Cyclopropylamine". J. Am. Chem. Soc..
  3. (1942). "The Reaction of Epichlorohydrin with the Grignard Reagent". J. Am. Chem. Soc..
  4. (1943). "The Reaction of Epichlorohydrin with the Grignard Reagent. Some Derivatives of Cyclopropanol". J. Am. Chem. Soc..
  5. "Antiviral compounds".
  6. "Modulators of protein trafficking".

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cycloalkanolscyclopropyl-compounds