Nitroacetic acid

Nitroacetic acid
Names
	Preferred IUPAC name Nitroacetic acid
	Other names Nitro acetate
Identifiers
CAS Number	625-75-2 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL571463 ;
ChemSpider	39723 ;
ECHA InfoCard	100.249.741
PubChem CID	43581;
UNII	6CMX4X7N84 ;
CompTox Dashboard (EPA)	DTXSID5058519 ;
	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)[N+](=O)[O-];
Properties
Chemical formula	C2H3NO4
Molar mass	105.049 g·mol−1
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 [77 °F], 100 kPa). verify (what is ?) 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 thermal decarboxylation of a corresponding salt to at 80 °C.^[2]

References

^ 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.
^ F. C. Whitmore and Marion G. Whitmore (1923). "Nitromethane". Organic Syntheses. 3: 83; Collected Volumes, vol. 1, p. 401.

[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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