Nitroacetic acid

Nitroacetic acid
IUPAC name 2-Nitroacetic acid
Other names Nitro acetate
Identifiers
CAS number	625-75-2 Y
PubChem	43581
ChEMBL	CHEMBL571463 N
Jmol-3D images	Image 1
SMILES C(C(=O)O)[N+](=O)[O-]
Properties
Molecular formula	C2H3NO4
Molar mass	105.05 g mol−1
Acidity (pKa)	1.68 [1]
N acid (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 heating a corresponding salt to decarboxylation at 80 °C.^[2]

References

1. ^ Dippy, J.F.J., Hughes, S.R.C., Rozanski, A., J. Chem. Soc., 1959, 2492.
2. ^ Organic Syntheses, Coll. Vol. 1, p.401 (1941); Vol. 3, p.83 (1923)