Ethenol

Structural formula
General
Surname	Ethenol
other names	Vinyl alcohol; Hydroxyethene; Hydroxyethylene;
Molecular formula	C 2 H 4 O
External identifiers / databases
EC number	209-183-3
ECHA InfoCard	100.008.350
PubChem	11199
Wikidata	Q409591
properties
Molar mass	44.05 g mol −1
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Ethenol , also known as vinyl alcohol , hydroxyethene or hydroxyethylene , is an unstable unsaturated alcohol ( alkenol ) with the chemical formula C ₂ H ₄ O (H ₂ C = CHOH).

Tautomerism

Tautomeric equilibrium between ethanal (acetaldehyde, left) and ethenol (vinyl alcohol, right)

Vinyl alcohol is the simplest enol ; it isomerizes in the free state under normal conditions immediately to its tautomer acetaldehyde , provided it is not stabilized - for example as an iron carbonyl or platinum complex Pt (acac) (η ² -C ₂ H ₃ OH) Cl. Ethenol ethers ( vinyl ethers ) and esters ( vinyl esters ) are also stable .

The thermoplastic polyvinyl alcohol (PVA or PVOH), which is derived from this monomer , can therefore only be produced indirectly through the polymerization of vinyl acetates and the subsequent hydrolysis of polyvinyl acetates .

Interstellar occurrence

Between May and June 2001, astronomers AJ Apponi and Barry E. Turner found ethenol in the Sagittarius B molecular cloud at the National Science Foundation's 12 m radio telescope at the Kitt Peak National Observatory .

Individual evidence

↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of vinyl alcohol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on April 8, 2018, is reproduced from a self-classification by the distributor .
↑ FA Cotton, JN Francis, BA Frenz, M. Tsutsui: Structure of a dihapto (vinyl alcohol) complex of platinum (II) , in: Journal of the American Chemical Society , 1973 , 95 , pp. 2483-2486. doi: 10.1021 / ja00789a011 .
↑ Entry on vinyl alcohol. In: Römpp Online . Georg Thieme Verlag, accessed on December 4, 2011.
↑ BE Turner, AJ Apponi: Microwave Detection of Interstellar Vinyl Alcohol, CH ₂ = CHOH , in: Astrophysical Journal , 561, L207-L210, 2001 November 10; Full text .

[1] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of vinyl alcohol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on April 8, 2018, is reproduced from a self-classification by the distributor .

[2] FA Cotton, JN Francis, BA Frenz, M. Tsutsui: Structure of a dihapto (vinyl alcohol) complex of platinum (II) , in: Journal of the American Chemical Society , 1973 , 95 , pp. 2483-2486. doi: 10.1021 / ja00789a011 .

[Römpp-3] Entry on vinyl alcohol. In: Römpp Online . Georg Thieme Verlag, accessed on December 4, 2011.

[4] BE Turner, AJ Apponi: Microwave Detection of Interstellar Vinyl Alcohol, CH ₂ = CHOH , in: Astrophysical Journal , 561, L207-L210, 2001 November 10; Full text .