Carbohydrazide is the chemical compound with the formula OC(N2H3)2. It appears as a white solid that is soluble in water,[1][2] but not in many organic solvents, such as ethanol, ether or benzene. It decomposes upon melting.[2] 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.
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IUPAC name
1,3-Diaminourea
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Other names
Carbohydrazine
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ECHA InfoCard | 100.007.126 |
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Properties | |
CH6N4O | |
Molar mass | 90.09 g/mol |
Density | 1.341 g/cm3 |
Melting point | 153–154 °C (307–309 °F; 426–427 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Industrially the compound is produced by treatment of urea with hydrazine:[3]
It can also be prepared by reactions of other C1-precursors with hydrazine, such as carbonate esters.[2] 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.[4]
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.[10]