Semicarbazide

Semicarbazide
Names
Skeletal formula of semicarbazide
Ball-and-stick model of the semicarbazide molecule
IUPAC name Aminourea^[1]
Identifiers
CAS Number	57-56-7 ^checkY
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28306 ^checkY
ChEMBL	ChEMBL903 ^checkY
ChemSpider	5008 ^checkY
ECHA InfoCard	100.000.308 Edit this at Wikidata
KEGG	C02077 ^checkY
PubChem CID	5196
UNII	37QUC23K2X ^checkY
CompTox Dashboard (EPA)	DTXSID7043823 Edit this at Wikidata
InChI InChI=1S/CH5N3O/c2-1(5)4-3/h3H2,(H3,2,4,5)^checkY Key: DUIOPKIIICUYRZ-UHFFFAOYSA-N^checkY 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	GHS06: Toxic GHS07: Exclamation mark
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)	[画像:NFPA 704 four-colored diamond] Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform Flammability 0: Will not burn. E.g. water Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen Special hazards (white): no code 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). checkY verify (what is ^checkY☒N ?) 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

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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

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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

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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

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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

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^ 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.