Semicarbazide

Semicarbazide
Names


IUPAC name Aminourea^[1]
Identifiers
CAS Number	57-56-7^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28306^Y
ChEMBL	ChEMBL903^Y
ChemSpider	5008^Y
ECHA InfoCard	100.000.308
KEGG	C02077^Y
PubChem CID	5196
UNII	37QUC23K2X^Y
CompTox Dashboard (EPA)	DTXSID7043823
InChI 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
SMILES C(=O)(N)NN
Properties
Chemical formula	H₂NNHC(=O)NH₂
Molar mass	75.08 g/mol
Melting point	96 °C
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H315, H319, H335
Precautionary statements	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
Safety data sheet (SDS)	[1]
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

Chemical compound

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:^[2]

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.^[3]

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 related compounds. 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.^[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.

References

^ CID 5196 from PubChem
^ Jean-Pierre Schirmann, Paul Bourdauducq "Hydrazine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a13_177.
^ John McMurry (1984). Organic Chemistry. Brooks/Cole. p. 676.
^ 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.
^ 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.