Semicarbazide
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| Names | |
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| IUPAC name
Aminourea[1]
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.000.308 |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| H2NNHC(=O)NH2 | |
| Molar mass | 75.08 g/mol |
| Melting point | 96 °C |
| Hazards | |
| GHS labelling: | |
 
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| Danger | |
| H301, H315, H319, H335 | |
| P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P330, P332+P313, P337+P313, P362, P403+P233, P405 | |
| NFPA 704 (fire diamond) | |
| Safety data sheet (SDS) | [1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Semicarbazide is the chemical compound with the formula OC(NH2)(N2H3). It is a water-soluble white solid. It is a derivative of urea.
Synthesis
[edit]The compound prepared by treating urea with hydrazine:[2]
- 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.[3]
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, occurrence, detection
[edit]Semicarbazide is used in preparing pharmaceuticals including nitrofuran antibacterials (furazolidone, nitrofurazone, nitrofurantoin) and related compounds. It is also a product of degradations of the blowing agent azodicarbonamide (ADC). Semicarbazide forms in heat-treated flour containing ADC as well as breads made from ADC-treated flour.[4][5]
Semicarbazide is used as a detection reagent in thin layer chromatography (TLC). Semicarbazide stains α-keto acids on the TLC plate, which can then be viewed under ultraviolet light.
See also
[edit]- Biurea - another product of reaction of urea with hydrazine
- Carbazide - structurally related with the general formula (R2NNH)2C(O)
- Semicarbazide-cadmium therapy
- thiosemicarbazide
References
[edit]- ^ CID 5196 from PubChem
- ^ 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.
- ^ 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.
- ^ Maria Beatriz de la Calle; Elke Anklam (2005). "Semicarbazide: occurrence in food products and state-of-the-art in analytical methods used for its determination". Anal. Bioanal. Chem. 382 (4): 968–977. doi:10.1007/s00216-005-3243-z. PMID 15947918. S2CID 10765283.