Glyoxal

Glyoxal
Skeletal formula of glyoxal
Skeletal formula of glyoxal
Space-filling model of glyox
Space-filling model of glyox
Names
Preferred IUPAC name
Oxaldehyde[1]
Systematic IUPAC name
Ethanedial[1]
Other names
Glyoxal[1]
Glyoxaldehyde
Oxalaldehyde
Ethanedialdehyde
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.160 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C2H2O2/c3-1-2-4/h1-2H checkY
    Key: LEQAOMBKQFMDFZ-UHFFFAOYSA-N checkY
  • InChI=1/C2H2O2/c3-1-2-4/h1-2H
    Key: LEQAOMBKQFMDFZ-UHFFFAOYAX
  • O=CC=O
Properties
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
1.044 J/(K·g)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
1
1
Flash point −4 °C (25 °F; 269 K)
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).
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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]

  1. ^ 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.
  2. ^ O'Neil, M.J. (2001): The Merck Index, 13th Edition, page 803.
  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.