Semicarbazide

Semicarbazide
Identifiers
CAS Number	57-56-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28306 ;
ChEMBL	ChEMBL903 ;
ChemSpider	5008 ;
ECHA InfoCard	100.000.308
KEGG	C02077 ;
PubChem CID	5196;
CompTox Dashboard (EPA)	DTXSID7043823 ;
	InChI InChI=1S/CH5N3O/c2-1(5)4-3/h3H2,(H3,2,4,5) Key: DUIOPKIIICUYRZ-UHFFFAOYSA-N ; InChI=1/CH5N3O/c2-1(5)4-3/h3H2,(H3,2,4,5) Key: DUIOPKIIICUYRZ-UHFFFAOYAJ;
	SMILES C(=O)(N)NN;
Properties
Chemical formula	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). verify (what is ?) 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.

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

Urea
Hydrazine
Thiosemicarbazide

References

^ Jean-Pierre Schirmann, Paul Bourdauducq "Hydrazine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a13_177.
^ 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

Compounds Containing a N-CO-N-N or More Complex Group

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[Ullmann-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.

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