Semicarbazide

Semicarbazide is the chemical compound with the formula OC(NH2)(N2H3). It is a water-soluble white solid. It is a derivative of urea.

Semicarbazide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.308
KEGG
UNII
  • InChI=1S/CH5N3O/c2-1(5)4-3/h3H2,(H3,2,4,5) Y
    Key: DUIOPKIIICUYRZ-UHFFFAOYSA-N Y
  • InChI=1/CH5N3O/c2-1(5)4-3/h3H2,(H3,2,4,5)
    Key: DUIOPKIIICUYRZ-UHFFFAOYAJ
  • C(=O)(N)NN
Properties
H2NNHC(=O)NH2
Molar mass 75.08 g/mol
Melting point 96 °C
Hazards
Safety data sheet
GHS labelling:
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)
2
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

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]

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.

Drug usage

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.[3] [4]

TLC

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

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. 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.
  4. 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.CS1 maint: uses authors parameter (link)
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