Vinyl alcohol

Vinyl alcohol
Displayed formula of ethenol	Ball-and-stick model of ethenol
Names
	IUPAC name Ethenol
	Other names Hydroxyethene; Hydroxyethylene
Identifiers
CAS Number	557-75-5 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL76101 ;
ChemSpider	10726 ;
ECHA InfoCard	100.008.350
PubChem CID	11199;
CompTox Dashboard (EPA)	DTXSID8051467 ;
	InChI InChI=1S/C2H4O/c1-2-3/h2-3H,1H2 Key: IMROMDMJAWUWLK-UHFFFAOYSA-N ; InChI=1S/C2H4O/c1-2-3/h2-3H,1H2; InChI=1S/C2H4O/c1-2-3/h2-3H,1H2 Key: IMROMDMJAWUWLK-UHFFFAOYSA-N;
	SMILES OC=C;
Properties
Chemical formula	C2H4O
Molar mass	44.053 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Vinyl alcohol, also called ethenol (IUPAC name), is an alcohol. It is not to be confused with the drinking alcohol, ethanol. With the formula Template:Carbon Template:Hydrogen₂CHTemplate:OxygenH, vinyl alcohol is an isomer of acetaldehyde and ethylene oxide. Under normal conditions, it converts (tautomerizes) to acetaldehyde:

Relationship to polyvinylalcohol

Because of the instability of vinyl alcohol, the thermoplastic polyvinyl alcohol (PVA or PVOH) is made indirectly by polymerization of vinyl acetate followed by hydrolysis of the ester bonds (Ac = acetyl, HOAc = acetic acid):

n CH₂=CHOAc → (CH₂-CHOAc)_n

(CH₂-CHOAc)_n + n H₂O → (CH₂-CHOH)_n + n HOAc

Several metal complexes are known that contain vinyl alcohol as a ligand. One example is Pt(acac)(η²-C₂H₃OH)Cl.^[1]

Vinyl alcohol was discovered in the molecular cloud Sagittarius B using the 12-meter radio telescope at the Kitt Peak National Observatory.^[2] This vinyl alcohol being stable in the (dilute) interstellar medium shows that its tautomerization is not unimolecular.

^ F. A. Cotton, J. N. Francis, B. A. Frenz, M. Tsutsui "Structure of a dihapto(vinyl alcohol) complex of platinum(II)" Journal of the American Chemical Society, 1973, volume 95, p. 2483-6. doi:10.1021/ja00789a011
^ "Scientists Toast the Discovery of Vinyl Alcohol in Interstellar Space". National Radio Astronomy Observatory. 2001-10-01. Retrieved 2006-12-20.