Carbohydrazide

Carbohydrazide

Names
IUPAC name 1,3-Diaminourea
Identifiers
CAS Number	497-18-7 Y
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:61308 Y
ChemSpider	66578 Y
ECHA InfoCard	100.007.126
PubChem	73948
InChI InChI=1S/CH6N4O/c2-4-1(6)5-3/h2-3H2,(H2,4,5,6) Y Key: XEVRDFDBXJMZFG-UHFFFAOYSA-N Y InChI=1/CH6N4O/c2-4-1(6)5-3/h2-3H2,(H2,4,5,6) Key: XEVRDFDBXJMZFG-UHFFFAOYAS
SMILES C(=O)(NN)NN O=C(NN)NN
Properties
Chemical formula	CH6N4O
Molar mass	90.09 g/mol
Density	1.341 g/cm3
Melting point	153 to 154 °C (307 to 309 °F; 426 to 427 K)
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

Carbohydrazide is the chemical compound with the formula OC(N₂H₃)₂. It is a white, water-soluble solid. It decomposes upon melting. A number of carbazides are known where one or more N-H groups are replaced by other substituents. They occur widely in the drugs, herbicides, plant growth regulators, and dyestuffs.

Industrially the compound is produced by treatment of urea with hydrazine:

It can also be prepared by reactions of other C1-precursors with hydrazine, such as carbonate esters. It can be prepared from phosgene, but this route cogenerates the hydrazinium salt [N₂H₅]Cl and results in some diformylation. Carbazic acid is also a suitable precursor:

The molecule is nonplanar. All nitrogen centers are at least somewhat pyramidal, indicative of weaker C-N pi-bonding. The C-N and C-O distances are about 1.36 and 1.25 Å, respectively.

Heating carbohydrazide may result in an explosion. Carbohydrazide is harmful if swallowed, irritating to eyes, respiratory system, and skin. Carbohydrazide is toxic to aquatic organisms.