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Nitroacetic acid

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Nitroacetic acid
Names
Preferred IUPAC name Nitroacetic acid
Other names Nitro acetate
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.249.741 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H3NO4/c4-2(5)1-3(6)7/h1H2,(H,4,5)Key: RGHXWDVNBYKJQH-UHFFFAOYSA-N
  • InChI=1/C2H3NO4/c4-2(5)1-3(6)7/h1H2,(H,4,5)Key: RGHXWDVNBYKJQH-UHFFFAOYAA
SMILES
  • C(C(=O)O)(=O)
Properties
Chemical formula C2H3NO4
Molar mass 105.049 g·mol
Density 1.5±0.1 g/cm3
Acidity (pKa) 1.68
Hazards
Flash point 150.6±11.1 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Nitroacetic acid is the chemical compound with the formula (NO2)CH2CO2H. This substituted carboxylic acid is used as a potential precursor to nitromethane, commonly used as a fuel in drag racing and as an organic reagent in chemical synthesis.

Synthesis

Nitroacetic acid can be synthesized by adding cold chloroacetic acid into a cold, slightly alkaline aqueous solution, followed by mixing with aqueous sodium nitrite solution. It is important during this procedure not to make the solution too alkaline and to keep it cold to prevent the formation of sodium glycolate.

Reactions

Nitroacetic acid can be used in the production of nitromethane by thermal decarboxylation of a corresponding salt to at 80 °C.

References

  1. Dippy, J. F. J.; Hughes, S. R. C.; Rozanski, A. (1959). "498. The dissociation constants of some symmetrically disubstituted succinic acids". Journal of the Chemical Society (Resumed): 2492. doi:10.1039/jr9590002492.
  2. F. C. Whitmore and Marion G. Whitmore (1923). "Nitromethane". Organic Syntheses. 3: 83; Collected Volumes, vol. 1, p. 401.
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