Semicarbazide

Semicarbazide
Skeletal formula of semicarbazide
Ball-and-stick model of the semicarbazide molecule
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.308
KEGG
Properties
H2NNHC(=O)NH2
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).
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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.

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

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 compound with sulfur atom in place of oxygen atom,[3] with 4-Methyl-3-thiosemicarbazide being a simple example.

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, occurrence, detection

Semicarbazide is used in preparing pharmaceuticals including: nitrofuran antibacterials (furazolidone, nitrofurazone, nitrofurantoin), and dizatrifone. It is also a product of degradation 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.

Structures

See also

References

  1. ↑ Jean-Pierre Schirmann, Paul Bourdauducq "Hydrazine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a13_177.
  2. ↑ John McMurry (1984). Organic Chemistry. Brooks/Cole. p. 676.
  3. ↑ "Thiosemicarbazide". PubChem.
  4. ↑ 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.
  5. ↑ 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: 968–977. doi:10.1007/s00216-005-3243-z.
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