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Cyanoacetamide

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2-Cyanoacetamide
Names
Preferred IUPAC name 2-Cyanoacetamide
Other names Malonamide nitrile
3-Nitrilopropionamide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.211 Edit this at Wikidata
EC Number
  • 203-531-8
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H4N2O/c4-2-1-3(5)6/h1H2,(H2,5,6)Key: DGJMPUGMZIKDRO-UHFFFAOYSA-N
SMILES
  • N#CCC(=O)N
Properties
Chemical formula C3H4N2O
Molar mass 84.078 g·mol
Density 1.163 g/cm
Melting point 119 to 121 °C (246 to 250 °F; 392 to 394 K)
Boiling point 351.2 °C (664.2 °F; 624.3 K)
Acidity (pKa) ca. 11
13.24
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H302, H315, H319, H335
Precautionary statements P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

2-Cyanoacetamide is an organic compound. It is an acetic amide with a nitrile functional group.

Uses

Cyanoacetamide is used in spectrofluorimetric methods to determine the activity of antihistamine H1 receptor antagonistic drugs such as ebastine, cetirizine dihydrochloride and fexofenadine hydrochloride.

Preparation

2-Cyanoacetamide is prepared from chloroacetic acid via Kolbe nitrile synthesis followed by Fischer esterification and ester aminolysis.

See also

References

  1. George H. Schenk (Jun 23, 2016). Organic Functional Group Analysis: Theory and Development. Elsevier. ISBN 9781483136073.
  2. Jay Sung; Si-Ying Hsu; Tzu-Hua Wang; Amanda Pan; Andrew Yeh (2006). "Kinetic studies of the reactions of pentacyanonitrosylferrate(2−) with ligands containing acidic methylene groups". Inorganica Chimica Acta. 359 (12): 3888–3894. doi:10.1016/j.ica.2006.04.042.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. Ibrahim, F.; Sharaf El-Din, M. K.; Eid, M.; Wahba, M. E. K. (2011). "Spectrofluorimetric Determination Of Some H1 Receptor Antagonist Drugs In Pharmaceutical Formulations And Biological Fluids". International Journal of Pharmaceutical Sciences and Research. 21 (8): 2056–2072. doi:10.13040/IJPSR.0975-8232.2(8).2056-72.
  4. Inglis, J. K. H. (1928). "Ethyl Cyanoacetate". Organic Syntheses. 8: 74. doi:10.15227/orgsyn.008.0074.
  5. Corson, B. B.; Scott, R. W.; Vose, C. E. (1941). "Cyanoacetamide". Organic Syntheses. 1: 179. doi:10.15227/orgsyn.009.0036.
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