Vinyl formate

Vinyl formate
Identifiers
CAS Number	692-45-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	193133;
ECHA InfoCard	100.010.665
EC Number	211-730-6;
PubChem CID	222465;
UNII	LFS2HF6ZYT;
CompTox Dashboard (EPA)	DTXSID20219233 ;
	InChI InChI=1S/C3H4O2/c1-2-5-3-4/h2-3H,1H2 Key: GFJVXXWOPWLRNU-UHFFFAOYSA-N;
	SMILES C=COC=O;
Properties
Chemical formula	C3H4O2
Molar mass	72.063 g·mol−1
Appearance	colorless liquid
Density	0.963 g/cm3
Boiling point	46.8–47.0 °C (116.2–116.6 °F; 319.9–320.1 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Vinyl formate is an organic compound with the formula CH₂=CHO₂CH. It is the ester formally derived from formic acid and vinyl alcohol. Although rare commercially, it occurs naturally.^[1]^[2] It can be prepared by transvinylation, say by treating vinyl versatate with formic acid in the presence of a mercury(II) catalyst..^[3]

References

^ Dan, T.; Wang, D.; Jin, R.L.; Zhang, H.P.; Zhou, T.T.; Sun, T.S. (2017). "Characterization of volatile compounds in fermented milk using solid-phase microextraction methods coupled with gas chromatography-mass spectrometry". Journal of Dairy Science. 100 (4): 2488–2500. doi:10.3168/jds.2016-11528. PMID 28161169.
^ Dekeirsschieter, Jessica; Stefanuto, Pierre-Hugues; Brasseur, Catherine; Haubruge, Eric; Focant, Jean-François (2012). "Enhanced Characterization of the Smell of Death by Comprehensive Two-Dimensional Gas Chromatography-Time-of-Flight Mass Spectrometry (GCXGC-TOFMS)". PLOS ONE. 7 (6): e39005. Bibcode:2012PLoSO...739005D. doi:10.1371/journal.pone.0039005. PMC 3377612. PMID 22723918.
^ Mondal, M.A.S.; Van Der Meer, R.; German, A.L.; Heikens, D. (1974). "A novel synthesis of vinyl esters from vinylversatate-10" (PDF). Tetrahedron. 30 (23–24): 4205–4207. doi:10.1016/S0040-4020(01)97407-1.

[1] Dan, T.; Wang, D.; Jin, R.L.; Zhang, H.P.; Zhou, T.T.; Sun, T.S. (2017). "Characterization of volatile compounds in fermented milk using solid-phase microextraction methods coupled with gas chromatography-mass spectrometry". Journal of Dairy Science. 100 (4): 2488–2500. doi:10.3168/jds.2016-11528. PMID 28161169.

[2] Dekeirsschieter, Jessica; Stefanuto, Pierre-Hugues; Brasseur, Catherine; Haubruge, Eric; Focant, Jean-François (2012). "Enhanced Characterization of the Smell of Death by Comprehensive Two-Dimensional Gas Chromatography-Time-of-Flight Mass Spectrometry (GCXGC-TOFMS)". PLOS ONE. 7 (6): e39005. Bibcode:2012PLoSO...739005D. doi:10.1371/journal.pone.0039005. PMC 3377612. PMID 22723918.

[3] Mondal, M.A.S.; Van Der Meer, R.; German, A.L.; Heikens, D. (1974). "A novel synthesis of vinyl esters from vinylversatate-10" (PDF). Tetrahedron. 30 (23–24): 4205–4207. doi:10.1016/S0040-4020(01)97407-1.

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