Semicarbazide
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| Identifiers | |
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57-56-7  |
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| 3D model (Jmol) | Interactive image |
| ChEBI | CHEBI:28306 |
| ChEMBL | ChEMBL903 |
| ChemSpider | 5008 |
| ECHA InfoCard | 100.000.308 |
| KEGG | C02077 |
| PubChem | 5196 |
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| Properties | |
| H2NNHC(=O)NH2 | |
| Molar mass | 75.08 g/mol |
| Melting point | 96 °C |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Semicarbazide is the chemical compound with the formula OC(NH2)(N2H3). It is a water-soluble white solid. It is a derivative of urea.
Contents
Synthesis[edit]
The compound prepared by treating urea with hydrazine:[1]
- OC(NH2)2 + N2H4 → OC(NH2)(N2H3) + NH3
A further reaction can occur to give carbohydrazide:
- OC(NH2)(N2H3) + N2H4 → OC(N2H3)2 + NH3
Derivatives[edit]
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.[2]
Thiosemicarbazide is the analogous compoound with sulfur atom in place of oxygen atom,[3] with 4-Methyl-3-thiosemicarbazide being a simple example.
Properties[edit]
Semicarbazide products (semicarbazones and thiosemicarbazones) are known to have an activity of antiviral, antiinfective and antineoplastic through binding to copper or iron in cells.
Uses[edit]
Semicarbazide is used in preparing pharmaceuticals including: nitrofuran antibacterials (furazolidone, nitrofurazone, nitrofurantoin) and dizatrifone.
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.
Occurrence[edit]
Semicarbazide has been shown to be formed in heat-treated flour containing azodicarbonamide as well as breads made from azodicarbonamide-treated flour.[4]
Structures[edit]
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Thiosemicarbazide
See also[edit]
- Biurea - the conceptual dimer
- Carbazide - structurally related with the general formula (R2NNH)2C(O)
- Semicarbazide-cadmium therapy
References[edit]
- ^ 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
|title=(help) - ^ Becalski, Adam; Lau, Benjamin; Lewis, David; Seaman, Stephen (2004). "Semicarbazide Formation in Azodicarbonamide-Treated Flour: A Model Study". J. Agric. Food Chem. 52 (18): 5730–4. doi:10.1021/jf0495385. PMID 15373416.
External links[edit]
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