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Cyclopropanol: Difference between revisions

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{{Chembox {{Chembox
| Watchedfields = changed
| verifiedrevid = 426640263 | verifiedrevid = 441485086
| Name = | Name =
| ImageFile = Cyclopropanol.svg | ImageFile = Cyclopropanol.svg
| ImageSize = 100px | ImageSize = 100px
| ImageAlt = | ImageAlt =
| ImageName = | ImageName =
| IUPACName = Cyclopropanol | PIN = Cyclopropanol
| OtherNames = Cyclopropyl alcohol, Hydroxycyclopropane
| SystematicName =
|Section1={{Chembox Identifiers
| OtherNames = Cyclopropyl alcohol, Hydroxycyclopropane
| 3DMet =
| Section1 = {{Chembox Identifiers
| 3DMet = | Abbreviations =
| Abbreviations = | Beilstein =
| CASNo_Ref = {{cascite|correct|??}}
| ATCvet =
| CASNo = 16545-68-9
| ATCCode_prefix =
| CASNoOther =
| ATCCode_suffix =
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ATC_Supplemental =
| Beilstein = | ChEBI =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| CASNo = 16545-68-9
| CASNo_Ref =
| CASNos =
| CASOther =
| ChEBI =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 109961 | ChemSpiderID = 109961
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| EC-number = | DrugBank =
| EINECS = | EC_number =
| EINECSCASNO = | EINECS =
| Gmelin = | Gmelin =
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C3H6O/c4-3-1-2-3/h3-4H,1-2H2 | StdInChI = 1S/C3H6O/c4-3-1-2-3/h3-4H,1-2H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YOXHCYXIAVIFCZ-UHFFFAOYSA-N | StdInChIKey = YOXHCYXIAVIFCZ-UHFFFAOYSA-N
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = | KEGG =
| MeSHName = | MeSHName =
| PubChem = 123361 | PubChem = 123361
| RTECS = | RTECS =
| SMILES = OC1CC1 | SMILES = OC1CC1
| UNNumber = | UNNumber =
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| AtmosphericOHRateConstant = | AtmosphericOHRateConstant =
| Appearance = | Appearance =
| BoilingPtC = 101 to 102
| BoilingPt = 101–102&nbsp;°C<ref name="enz synth">{{cite journal |journal= Tetrahedron Lett. |year= 1987 |volume= 28 |issue= 24 |pages= 2767–2768 |title= Enzymatic hydrolysis of cyclopropyl acetate. A facile method for medium- and large-scale preparations of cyclopropanol |authors= Jongejan, J. A.; Duine, J. A. |doi= 10.1016/S0040-4039(00)96204-X }}</ref> | BoilingPt_ref = <ref name="enz synth">{{cite journal |journal= Tetrahedron Lett. |year= 1987 |volume= 28 |issue= 24 |pages= 2767–2768 |title= Enzymatic hydrolysis of cyclopropyl acetate. A facile method for medium- and large-scale preparations of cyclopropanol |author1=Jongejan, J. A. |author2=Duine, J. A. |doi= 10.1016/S0040-4039(00)96204-X }}</ref>
| Boiling_notes =
| BoilingPt_notes =
| Density = 0.917&nbsp;g/mL<ref name=roberts>{{cite journal |title= Small-Ring Compounds. VI. Cyclopropanol, Cyclopropyl Bromide and Cyclopropylamine |authors= Roberts, J. D.; Chambers, V. C. |journal= J. Am. Chem. Soc. |year= 1951 |volume= 73 |issue= 7 |pages= 3176–3179 |doi= 10.1021/ja01151a053 }}</ref> | Density = 0.917&nbsp;g/mL<ref name=roberts>{{cite journal |title= Small-Ring Compounds. VI. Cyclopropanol, Cyclopropyl Bromide and Cyclopropylamine |author1=Roberts, J. D. |author2=Chambers, V. C. |journal= J. Am. Chem. Soc. |year= 1951 |volume= 73 |issue= 7 |pages= 3176–3179 |doi= 10.1021/ja01151a053 }}</ref>
| C=3 | H=6 | O=1
| HenryConstant = | C=3 | H=6 | O=1
| LogP = | HenryConstant =
| Melting_notes = | LogP =
| pKa = | MeltingPt_notes =
| pKb = | pKa =
| Solubility = | pKb =
| Solubility =
| SolubleOther = | SolubleOther =
| Solvent = | Solvent =
| VaporPressure =}} | VaporPressure =}}
| Section3 = {{Chembox Structure |Section3={{Chembox Structure
| Coordination = | Coordination =
| CrystalStruct = | CrystalStruct =
| MolShape = }} | MolShape = }}
| Section4 = {{Chembox Thermochemistry |Section4={{Chembox Thermochemistry
| DeltaHc = | DeltaHc =
| DeltaHf = | DeltaHf =
| Entropy = | Entropy =
| HeatCapacity = }} | HeatCapacity = }}
| Section8 = {{Chembox Related |Section8={{Chembox Related
| Function = | OtherFunction_label =
| OtherAnions = | OtherAnions =
| OtherCations = | OtherCations =
| OtherCpds = | OtherCompounds =
| OtherFunctn = }} | OtherFunction =
}}
}} }}


'''Cyclopropanol''' is an organic compound with the chemical formula C<sub>3</sub>H<sub>6</sub>O. It contains a ] group with an ] 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 ]ization to form ].<ref name=magrane>{{cite journal |title= The Reaction of Epichlorohydrin with the Grignard Reagent |authors= Magrane, J. K.; Cottle, D. L. |journal= J. Am. Chem. Soc. |volume= 64 |year= 1942 |issue= 3 |pages= 484–487 |doi= 10.1021/ja01255a004 }}</ref><ref name=stahl>{{cite journal| title= The Reaction of Epichlorohydrin with the Grignard Reagent. Some Derivatives of Cyclopropanol |authors= Stahl, G. W.; Cottle, D. L. |journal= J. Am. Chem. Soc. |volume= 65 |issue= 9 |year= 1943 |pages= 1782–1783 |doi= 10.1021/ja01249a507 }}</ref> This property is useful synthetically: cyclopropanol can be used as a ] for the homo] of propanal. The chemical is also useful as a reagent to introduce a cyclopropyl group into ], ], and ] linkages. The resulting cyclopropyl-containing compounds have been used in investigations of potential ] drugs<ref name="cottell patent">{{cite patent |title= Antiviral compounds |inventor= Cottell, J. J.; Link, J. O. Schroeder, S. D.; Taylor, J.; Tse, W.; Vivian, R. W.; Yang, Z.-Y. |country= WO |number= 2009005677 |status= application |pubdate= 2009-01-08 }}</ref> and of modulators of ] trafficking.<ref name="bulawa patent">{{cite patent |title= Modulators of protein trafficking |inventor= Bulawa, C. E.; Devit, M.; Elbaum, D. |country= WO |number= 2009062118 |status= application |pubdate= 2009-05-14 }}</ref> '''Cyclopropanol''' is an organic compound with the chemical formula C<sub>3</sub>H<sub>6</sub>O. It contains a ] group with a ] 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 ], undergoing ]ization to form ].<ref name=magrane>{{cite journal |title= The Reaction of Epichlorohydrin with the Grignard Reagent |author1=Magrane, J. K. |author2=Cottle, D. L. |journal= J. Am. Chem. Soc. |volume= 64 |year= 1942 |issue= 3 |pages= 484–487 |doi= 10.1021/ja01255a004 }}</ref><ref name=stahl>{{cite journal| title= The Reaction of Epichlorohydrin with the Grignard Reagent. Some Derivatives of Cyclopropanol |author1=Stahl, G. W. |author2=Cottle, D. L. |journal= J. Am. Chem. Soc. |volume= 65 |issue= 9 |year= 1943 |pages= 1782–1783 |doi= 10.1021/ja01249a507 }}</ref> This property is useful synthetically: cyclopropanol can be used as a ] for the homo] of propanal. The chemical is also useful as a reagent to introduce a cyclopropyl group into ], ], and ] linkages. The resulting cyclopropyl-containing compounds have been used in investigations of potential ]s<ref name="cottell patent">{{cite patent |title= Antiviral compounds |inventor= Cottell, J. J.; Link, J. O. Schroeder, S. D.; Taylor, J.; Tse, W.; Vivian, R. W.; Yang, Z.-Y. |country= WO |number= 2009005677 |status= application |pubdate= 2009-01-08 }}</ref> and of modulators of ] trafficking.<ref name="bulawa patent">{{cite patent |title= Modulators of protein trafficking |inventor= Bulawa, C. E.; Devit, M.; Elbaum, D. |country= WO |number= 2009062118 |status= application |pubdate= 2009-05-14 }}</ref>


== References == == References ==
{{reflist}} {{reflist}}


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