Cyclobutanol
Names
Preferred IUPAC name
Cyclobutanol
Other names
Cyclobutyl alcohol, Hydroxycyclobutane
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.018.963
EC Number
  • 220-858-1
UNII
  • InChI=1S/C4H8O/c5-4-2-1-3-4/h4-5H,1-3H2 checkY
    Key: KTHXBEHDVMTNOH-UHFFFAOYSA-N checkY
  • OC1CCC1
Properties
C4H8O
Molar mass 72.107 g·mol−1
Hazards
GHS labelling:
GHS02: Flammable
Danger
H225
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).
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Infobox references

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]

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

  1. ↑ "Safety Data Sheet". Sigma-Aldrich. Millipore Sigma. 2 Oct 2022. Archived from the original on 4 Nov 2023. Retrieved 4 Nov 2023.
  2. ↑ 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. ISSN 0108-7681.
  3. ↑ 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.
  4. 1 2 US6958421B2, Bodmann, Kerstin; Imig, Manuela & Köhler, Günther et al., "Salt-free preparation of cyclobutanone", issued 2005-10-25
  5. ↑ 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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