Glyoxal

Glyoxal
Skeletal formula of glyoxal	Space-filling model of glyox
Names
	Preferred IUPAC name Oxaldehyde
	Systematic IUPAC name Ethanedial
	Other names Glyoxal; Glyoxaldehyde; Oxalaldehyde; Ethanedialdehyde
Identifiers
CAS Number	107-22-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:34779 ;
ChemSpider	7572 ;
ECHA InfoCard	100.003.160
KEGG	C14448 ;
PubChem CID	7860;
UNII	50NP6JJ975 ;
CompTox Dashboard (EPA)	DTXSID5025364 ;
	InChI InChI=1S/C2H2O2/c3-1-2-4/h1-2H Key: LEQAOMBKQFMDFZ-UHFFFAOYSA-N ; InChI=1/C2H2O2/c3-1-2-4/h1-2H Key: LEQAOMBKQFMDFZ-UHFFFAOYAX;
	SMILES O=CC=O;
Properties
Chemical formula	C2H2O2
Molar mass	58.036 g·mol−1
Melting point	15 °C (59 °F; 288 K)
Boiling point	51 °C (124 °F; 324 K)
Thermochemistry
Heat capacity (C)	1.044 J/(K·g)
Hazards
NFPA 704 (fire diamond)	2 1 1
Flash point	−4 °C (25 °F; 269 K)
Autoignition; temperature	285 °C (545 °F; 558 K)
Related compounds
Related aldehydes	acetaldehyde; glycolaldehyde; propanedial; methylglyoxal
Related compounds	glyoxylic acid; glycolic acid; oxalic acid; pyruvic acid; diacetyl; acetylacetone
	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

Glyoxal is an organic compound with the chemical formula OCHCHO. It is the smallest dialdehyde (a compound with two aldehyde groups). It is a crystalline solid, white at low temperatures and yellow near the melting point (15 °C). The liquid is yellow, and the vapor is green.^[2]

Pure glyoxal is not commonly encountered because glyoxal is usually handled as a 40% aqueous solution (density near 1.24 g/mL). It forms a series of hydrates, including oligomers. For many purposes, these hydrated oligomers behave equivalently to glyoxal. Glyoxal is produced industrially as a precursor to many products.^[3]

^ ^a ^b ^c "Characteristic (Functional) and Substituent Groups". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 415, 417. doi:10.1039/9781849733069-00372. ISBN 978-0-85404-182-4.
^ O'Neil, M.J. (2001): The Merck Index, 13th Edition, page 803.
^ Mattioda, Georges; Blanc, Alain. "Glyoxal". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a12_491.pub2. ISBN 978-3527306732.

[iupac2013-1] "Characteristic (Functional) and Substituent Groups". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 415, 417. doi:10.1039/9781849733069-00372. ISBN 978-0-85404-182-4.

[merck-2] O'Neil, M.J. (2001): The Merck Index, 13th Edition, page 803.

[Ullmann-3] Mattioda, Georges; Blanc, Alain. "Glyoxal". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a12_491.pub2. ISBN 978-3527306732.

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