Semicarbazide

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Semicarbazide
Skeletal formula of semicarbazide
Ball-and-stick model of the semicarbazide molecule
Identifiers
57-56-7 YesY
ChEBI CHEBI:28306 YesY
ChEMBL ChEMBL903 YesY
ChemSpider 5008 YesY
Jmol 3D model Interactive image
KEGG C02077 YesY
PubChem 5196
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[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]

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[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 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[edit]

Semicarbazide has been shown to be formed in heat-treated flour containing azodicarbonamide as well as breads made from azodicarbonamide-treated flour.[2]

Structures[edit]

See also[edit]

References[edit]

  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. ^ 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. 

External links[edit]