Semicarbazide

Semicarbazide
Skeletal formula of semicarbazide
Ball-and-stick model of the semicarbazide molecule
Identifiers
57-56-7 Yes
ChEBI CHEBI:28306 Yes
ChEMBL ChEMBL903 Yes
ChemSpider 5008 Yes
Jmol-3D images Image
KEGG C02077 Yes
PubChem 5196
Properties
H2NNHC(=O)NH2
Molar mass 75.08 g/mol
Melting point 96 °C
Except where noted otherwise, data is 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.

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.

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.

External links