|Jmol interactive 3D||Image
|Molar mass||90.09 g/mol|
|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).
|what is ?)(|
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:
- 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
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.
- 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.
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.
- Inorganic Syntheses Volume IV. McGraw-Hill Book Company, Inc. 1953. p. 35.
- Kurzer, Frederick; Michael Wilkinson (February 1970). "Chemistry of carbohydrazide and thiocarbohydrazide". ACS Chemical Reviews. doi:10.1021/cr60263a004.
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