cyclobutanol

{{Chembox

| Watchedfields = changed

| verifiedrevid = 441485086

| Name =

| ImageFile = Cyclobutanol.svg

| ImageSize = 100px

| ImageAlt =

| ImageName =

| PIN = Cyclobutanol

| OtherNames = Cyclobutyl alcohol, Hydroxycyclobutane

|Section1={{Chembox Identifiers

| 3DMet =

| Abbreviations =

| Beilstein =

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 2919-23-5

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = AD482C8GST

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 68700

| EC_number = 220-858-1

| Gmelin =

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C4H8O/c5-4-2-1-3-4/h4-5H,1-3H2

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = KTHXBEHDVMTNOH-UHFFFAOYSA-N

| KEGG =

| MeSHName =

| PubChem = 76218

| RTECS =

| SMILES = OC1CCC1

| ChEMBL = 449234

}}

|Section2={{Chembox Properties

| AtmosphericOHRateConstant =

| Appearance =

| BoilingPtC =

| BoilingPt_ref =

| BoilingPt_notes =

| Density =

| C=4 | H=8 | 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 = }}

|Section7={{Chembox Hazards

| GHSPictograms = {{GHS02}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|225}}

| PPhrases = {{P-phrases|210|233|240|241|242|243|280|303+361+353|370+378|403+235|501}}

}}

|Section8={{Chembox Related

| OtherFunction_label =

| OtherAnions =

| OtherCations =

| OtherCompounds = cyclopropanol; cyclopentanol; cyclohexanol

| OtherFunction = cyclobutane; cyclobutanone; cyclobutene

}}

}}

{{Expand language|langcode=el|otherarticle=Κυκλοβουτανόλη|langcode2=zh|otherarticle2=環丁醇}}

Cyclobutanol is an organic compound with the chemical formula C4H8O; it is defined as a cyclobutyl group with a hydroxyl group pendant and thus a cycloalkanol. Physically, it is a yellowish clear liquid that crystallizes orthorhombically at low-temperatures.

Cyclobutylamine's Demjanov rearrangement with nitrous acid gives cyclobutanol, and cyclopropylmethanol rearranges in strong acid to the same. Metal hydrides reduce cyclobutanone to cyclobutanol; conversely, cyclobutanol oxidation is a salt-free route to cyclobutanone.

References

{{Cite patent|number=US6958421B2|title=Salt-free preparation of cyclobutanone|gdate=2005-10-25|invent1=Bodmann|invent2=Imig|invent3=Köhler|invent4=Brühl|inventor1-first=Kerstin|inventor2-first=Manuela|inventor3-first=Günther|inventor4-first=Karl-Heinz|url=https://patents.google.com/patent/US6958421/en}}

{{Cite book |last1=Breitmaier |first1=Eberhard |url=https://books.google.com/books?id=Ld-AGnffxXIC&pg=PA116 |title=Organische Chemie: Grundlagen, Stoffklassen, Reaktionen, Konzepte, Molekülstrukturen |last2=Jung |first2=Günther |date=2005 |publisher=Georg Thieme Verlag |isbn=978-3-13-541505-5 |page=116 |language=de}}

{{Cite journal |last1=McGregor |first1=Pamela A. |last2=Allan |first2=David R. |last3=Parsons |first3=Simon |last4=Pulham |first4=Colin R. |date=2005-08-01 |title=The low-temperature and high-pressure crystal structures of cyclobutanol (C4H7OH) |url=https://journals.iucr.org/b/issues/2005/04/00/ws5024/index.html |journal=Acta Crystallographica Section B Structural Science |volume=61 |issue=4 |pages=449–454 |doi=10.1107/S0108768105019191 |issn=0108-7681 |doi-access=free|hdl=20.500.11820/d33aabb3-f547-4233-8af2-976630e51d81 |hdl-access=free }}

{{Cite web |date=2 Oct 2022 |title=Safety Data Sheet |url=https://www.sigmaaldrich.com/US/en/sds/ALDRICH/156434 |url-status=live |archive-url=https://web.archive.org/web/20231104230526/https://www.sigmaaldrich.com/US/en/sds/ALDRICH/156434 |archive-date=4 Nov 2023 |access-date=4 Nov 2023 |website=Sigma-Aldrich |publisher=Millipore Sigma}}

{{Cite book |last1=Vollhardt |first1=Kurt Peter C. |url=https://books.google.com/books?id=3eIXefCwsEMC&pg=PA329 |title=Organische Chemie |last2=Schore |first2=Neil Eric |date=2011 |publisher=John Wiley & Sons |isbn=978-3-527-32754-6 |page=329 |language=de}}

Category:Cycloalkanols

Category:Cyclobutyl compounds

{{organic-compound-stub}}