Cyanoacetamide

2-Cyanoacetamide
Names
Preferred IUPAC name
2-Cyanoacetamide
Other names
Malonamide nitrile
3-Nitrilopropionamide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.211 Edit this at Wikidata
EC Number
  • 203-531-8
UNII
  • InChI=1S/C3H4N2O/c4-2-1-3(5)6/h1H2,(H2,5,6)
    Key: DGJMPUGMZIKDRO-UHFFFAOYSA-N
  • N#CCC(=O)N
Properties
C3H4N2O
Molar mass 84.078 g·mol−1
Density 1.163 g/cm3
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[1]
13.24[2]
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302, H315, H319, H335
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 [77 °F], 100 kPa).

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.[3]

Preparation

2-Cyanoacetamide is prepared from chloroacetic acid via Kolbe nitrile synthesis[4] followed by Fischer esterification and ester aminolysis.[5]

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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