|3D model (Jmol)||Interactive image|
|Molar mass||75.08 g/mol|
|Melting point||96 °C|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|(what is ?)|
Semicarbazide is the chemical compound with the formula OC(NH2)(N2H3). It is a water-soluble white solid. It is a derivative of urea.
- OC(NH2)2 + N2H4 → OC(NH2)(N2H3) + NH3
A further reaction can occur to give carbohydrazide:
- OC(NH2)(N2H3) + N2H4 → OC(N2H3)2 + NH3
Semicarbazide is frequently reacted with aldehydes and ketones to produce semicarbazones via a condensation reaction. This is an example of imine formation resulting from the reaction of a primary amine with a carbonyl group. The reaction is useful because semicarbazones, like oximes and 2,4-DNPs, typically have high melting points and crystallize, facilitating purification or identification of reaction products.
Thiosemicarbazide is the analogous compoound with sulfur atom in place of oxygen atom, with 4-Methyl-3-thiosemicarbazide being a simple example.
Semicarbazide is used as a detection reagent in thin layer chromatography (TLC). Semicarbazide stains α-keto acids on the TLC plate, which must then be viewed under ultraviolet light to see the results.
Semicarbazide has been shown to be formed in heat-treated flour containing azodicarbonamide as well as breads made from azodicarbonamide-treated flour.
- Biurea - the conceptual dimer
- Carbazide - structurally related with the general formula (R2NNH)2C(O)
- Semicarbazide-cadmium therapy
- Jean-Pierre Schirmann, Paul Bourdauducq "Hydrazine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a13_177.
- John McMurry (1984). Organic Chemistry. Brooks/Cole. p. 676.
- . PubChem https://pubchem.ncbi.nlm.nih.gov/compound/2723789. Missing or empty
- Becalski, Adam; Lau, Benjamin; Lewis, David; Seaman, Stephen (2004). "Semicarbazide Formation in Azodicarbonamide-Treated Flour: A Model Study". J. Agric. Food Chem. 52 (18): 5730. doi:10.1021/jf0495385.