Nitroacetic acid

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.

Nitroacetic acid
Names
Preferred IUPAC name
Nitroacetic acid
Other names
Nitro acetate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.249.741
UNII
  • InChI=1S/C2H3NO4/c4-2(5)1-3(6)7/h1H2,(H,4,5) ☒N
    Key: RGHXWDVNBYKJQH-UHFFFAOYSA-N ☒N
  • InChI=1/C2H3NO4/c4-2(5)1-3(6)7/h1H2,(H,4,5)
    Key: RGHXWDVNBYKJQH-UHFFFAOYAA
  • C(C(=O)O)[N+](=O)[O-]
Properties
C2H3NO4
Molar mass 105.049 g·mol−1
Density 1.5±0.1 g/cm3
Acidity (pKa) 1.68 [1]
Hazards
Flash point 150.6±11.1 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.[2]

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.; Collective Volume, vol. 1, p. 401
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