Semicarbazide

Semicarbazide

Identifiers
CAS Number	57-56-7 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:28306 Y
ChEMBL	ChEMBL903 Y
ChemSpider	5008 Y
ECHA InfoCard	100.000.308
KEGG	C02077 Y
PubChem	5196
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
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.

The compound prepared by treating urea with hydrazine:

A further reaction can occur to give carbohydrazide:

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.

Thiosemicarbazide is the analogous compound with sulfur atom in place of oxygen atom, with 4-Methyl-3-thiosemicarbazide being a simple example.

Semicarbazide products (semicarbazones and thiosemicarbazones) are known to have an activity of antiviral, antiinfective and antineoplastic through binding to copper or iron in cells.

Semicarbazide is used in preparing pharmaceuticals including: nitrofuran antibacterials (furazolidone, nitrofurazone, nitrofurantoin) and dizatrifone.