Cyclobutanol

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^[1] that crystallizes orthorhombically at low-temperatures.^[2]

Cyclobutanol
Names

Preferred IUPAC name Cyclobutanol
Other names Cyclobutyl alcohol, Hydroxycyclobutane
Identifiers
CAS Number	2919-23-5^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL449234
ChemSpider	68700^Y
ECHA InfoCard	100.018.963
EC Number	220-858-1
PubChem CID	76218
UNII	AD482C8GST^Y
CompTox Dashboard (EPA)	DTXSID5062712
InChI InChI=1S/C4H8O/c5-4-2-1-3-4/h4-5H,1-3H2^Y Key: KTHXBEHDVMTNOH-UHFFFAOYSA-N^Y
SMILES OC1CCC1
Properties
Chemical formula	C₄H₈O
Molar mass	72.107 g·mol⁻¹
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225
Precautionary statements	P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, P501
Related compounds
Related	cyclobutane; cyclobutanone; cyclobutene
Related compounds	cyclopropanol; cyclopentanol; cyclohexanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

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Cyclobutylamine's Demjanov rearrangement with nitrous acid gives cyclobutanol,^[3] and cyclopropylmethanol rearranges in strong acid to the same.^[4] Metal hydrides reduce cyclobutanone to cyclobutanol;^[5] conversely, cyclobutanol oxidation is a salt-free route to cyclobutanone.^[4]

References

^ "Safety Data Sheet". Sigma-Aldrich. Millipore Sigma. 2 Oct 2022. Archived from the original on 4 Nov 2023. Retrieved 4 Nov 2023.

^ McGregor, Pamela A.; Allan, David R.; Parsons, Simon; Pulham, Colin R. (2005-08-01). "The low-temperature and high-pressure crystal structures of cyclobutanol (C₄H₇OH)". Acta Crystallographica Section B Structural Science. 61 (4): 449–454. doi:10.1107/S0108768105019191. hdl:20.500.11820/d33aabb3-f547-4233-8af2-976630e51d81. ISSN 0108-7681.

^ Breitmaier, Eberhard; Jung, Günther (2005). Organische Chemie: Grundlagen, Stoffklassen, Reaktionen, Konzepte, Molekülstrukturen (in German). Georg Thieme Verlag. p. 116. ISBN 978-3-13-541505-5.

^ ^a ^b US6958421B2, Bodmann, Kerstin; Imig, Manuela & Köhler, Günther et al., "Salt-free preparation of cyclobutanone", issued 2005-10-25

^ Vollhardt, Kurt Peter C.; Schore, Neil Eric (2011). Organische Chemie (in German). John Wiley & Sons. p. 329. ISBN 978-3-527-32754-6.

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