Semicarbazide
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| Identifiers | |
|---|---|
57-56-7  |
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| ChEBI | CHEBI:28306 |
| ChEMBL | ChEMBL903 |
| ChemSpider | 5008 |
| Jmol 3D model | Interactive image |
| 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). This water-soluble white solid is also known as carbohydrazide. It is a derivative of urea.
Contents
Synthesis
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
A thiosemicarbazide is the analog with sulfur atom in place of oxygen atom, with 4-Methyl-3-thiosemicarbazide being a simple example. Semicarbazones are derived by the condensation reaction between a ketone (or aldehyde) and a semicarbazide.
Properties
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
Semicarbazide is used in preparing pharmaceuticals including nitrofuran antibacterials (furazolidone, nitrofurazone, nitrofurantoin) and related compounds. 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
Semicarbazide has been shown to be formed in heat-treated flour containing azodicarbonamide as well as breads made from azodicarbonamide-treated flour.[2]
Structures
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Thiosemicarbazide
See also
- Biurea - the conceptual dimer
- Carbazide - structurally related with the general formula (R2NNH)2C(O)
- Semicarbazide-cadmium therapy
References
- ↑ Jean-Pierre Schirmann, Paul Bourdauducq "Hydrazine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a13_177.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
External links
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