Cyclopropanol

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Structural formula
Structural formula of cyclopropanol
General
Surname Cyclopropanol
Molecular formula C 3 H 6 O
External identifiers / databases
CAS number 16545-68-9
EC number 690-605-1
ECHA InfoCard 100.217.724
PubChem 123361
Wikidata Q3560539
properties
Molar mass 58.08 g mol −1
Physical state

liquid

safety instructions
GHS labeling of hazardous substances
02 - Highly / extremely flammable 07 - Warning

Caution

H and P phrases H: 226-315-319-335
P: 260-280-303 + 361 + 353-304 + 340-305 + 351 + 338-370 + 378
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cyclopropanol is an organic chemical compound from the group of cycloalkanols . It contains a cyclopropyl group with a hydroxyl group . Due to the three-membered ring, the compound is very unstable and quickly undergoes ring-opening reactions. Cyclopropanol is susceptible to rearrangement ( isomerization ) to propanal :

Rearrangement of cyclopropanol





Extraction and presentation

Cyclopropanol can be obtained by reacting ethyl magnesium bromide with epichlorohydrin . Derivatives of the compound can be prepared by the Kulinkovich reaction . Biosynthesis from cyclopropane and other synthetic routes are also known.

Individual evidence

  1. ↑ a b c Fluorochem: Safety Data Sheet , accessed December 27, 2019.
  2. ↑ JK Magrane, DL Cottle: The reaction of epichlorohydrin with the Grignard reagent. In: Journal of the American Chemical Society. 64, 1942, p. 484, doi: 10.1021 / ja01255a004 .
  3. ^ Glenn W. Stahl, DL Cottle: The Reaction of Epichlorohydrin with the Grignard Reagent. Some Derivatives of Cyclopropanol. In: Journal of the American Chemical Society. 65, 1943, p. 1782, doi: 10.1021 / ja01249a507 .
  4. ↑ John D. Roberts, Vaughan C. Chambers: Small-Ring Compounds. VI. Cyclopropanol, Cyclopropyl Bromide and Cyclopropylamine. In: Journal of the American Chemical Society. 73, 1951, p. 3176, doi: 10.1021 / ja01151a053 .
  5. ↑ John J. Eisch, Adetenu A. Adeosun, John N. Gitua: Mechanism of the Kulinkovich Cyclopropanol Synthesis: Transfer-Epititanation of the Alkene in Generating the Key Titanacyclopropane Intermediate. In: European Journal of Organic Chemistry. 2003, 2003, p. 4721, doi: 10.1002 / ejoc.200300588 .
  6. ^ J. Salaün, MS Baird: Biologicaliy Active Cyclopropanes and Cyclopropenes . In: Current Medicinal Chemistry . Vol. 2, No. 1 , 1995, p. 511–542, here p. 512 ( limited preview in Google book search).
  7. ↑ FJ McQuillin, MS Baird: Alicyclic Chemistry: . CUP Archive, 1983, ISBN 978-0-521-28391-5 , pp. 102 ( limited preview in Google Book search).