Oxiranol

Last updated
Oxiranol
Oxiranol.svg
Names
Preferred IUPAC name
Oxiranol
Other names
  • 2-Oxiranol
  • Epoxyethanol
  • Hydroxyoxirane
  • Oxacyclopropanol
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C2H4O2/c3-2-1-4-2/h2-3H,1H2
    Key: DOAMZWOPDPPKJS-UHFFFAOYSA-N
  • C1OC1O
Properties
C2H4O2
Molar mass 60.052 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Oxiranol is an organic chemical that is an alcohol derivative of oxirane: it consists of a hydroxy group as substituent on ethylene oxide. It can have two enantiomeric forms. The compound has been proposed as an intermediate in the interstellar formation of glycolaldehyde [1] (a constitutional isomer of oxiranol) and the oxidation of acrolein in the environment. [2]

It can be produced by reacting carbene with formic acid. To reduce the co-production of by-products, a mixture of diiodomethane (CH2I2) and zinc (with copper as catalyst) can be used as a carbene source. The production of carbene with this mixture favors the production of cyclic derivatives.

References

  1. ↑ Wang, Tianfang; Bowie, John H. (2010). "Radical routes to interstellar glycolaldehyde. The possibility of stereoselectivity in gas-phase polymerization reactions involving CH2O and ·CH2OH". Org. Biomol. Chem. 8 (20): 4757–4766. doi:10.1039/C0OB00125B. PMID   20714667.
  2. ↑ Asatryan, Rubik; da Silva, Gabriel; Bozzelli, Joseph W. (2010). "Quantum Chemical Study of the Acrolein (CH2CHCHO) + OH + O2 Reactions". J. Phys. Chem. A. 114 (32): 8302–8311. Bibcode:2010JPCA..114.8302A. doi:10.1021/jp104828a. PMID   20701337.


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