Carbohydrazide

Carbohydrazide

Names
IUPAC name 1,3-Diaminourea
Identifiers
CAS Number	497-18-7 Y
ChEBI	CHEBI:61308 Y
ChemSpider	66578 Y
Jmol 3D model	Interactive image Interactive image
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)
Vapor pressure	{{{value}}}
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

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.

Production

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

OC(NH₂)₂ + 2 N₂H₄ → OC(N₂H₃)₂ + 2 NH₃

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:

N₂NH₃CO₂H + N₂H₄ → OC(N₂H₃)₂ + H₂O

Structure

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.

Industrial uses

• Oxygen scrubber: carbohydrazide is used to remove oxygen in boiler systems. Oxygen scrubbers prevent corrosion.
• Precursor to polymers: carbohydrazide can be used as a curing agent for epoxide-type resins.
• Photography: carbohyrazide is used in the silver halide diffusion process as one of the toners. Carbohydrazide is used to stabilize color developers that produce images of the azo-methine and azine classes.
• Carbohydrazide has been used to develop ammunition propellants, stabilize soaps, and used a reagent in organic synthesis.

Hazards

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.