Carbohydrazide

Carbohydrazide

Names
IUPAC name 1,3-Diaminourea
Identifiers
CAS Number	497-18-7
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:61308
ChemSpider	66578
ECHA InfoCard	100.007.126
PubChem	73948
InChI InChI=1S/CH6N4O/c2-4-1(6)5-3/h2-3H2,(H2,4,5,6) Key: XEVRDFDBXJMZFG-UHFFFAOYSA-N 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/cm^3
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).
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Infobox references

Carbohydrazide is the chemical compound with the formula OC(N₂H₃)₂. It is a white, water-soluble solid.^[1][2] 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.

Production

Industrially the compound is produced by treatment of urea with hydrazine:^[3]

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.^[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:

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.^[4]

Industrial uses

• Oxygen scrubber: carbohydrazide is used to remove oxygen in boiler systems. Oxygen scrubbers prevent corrosion.^[5][6]
• Precursor to polymers: carbohydrazide can be used as a curing agent for epoxide-type resins.^[2]
• 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.^[2]
• Carbohydrazide has been used to develop ammunition propellants,^[7] stabilize soaps,^[2] 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.^[8]

References

1. Inorganic Syntheses Volume IV. McGraw-Hill Book Company, Inc. 1953. p. 35.
2. Kurzer, Frederick; Michael Wilkinson (February 1970). "Chemistry of carbohydrazide and thiocarbohydrazide". Chemical Reviews. doi:10.1021/cr60263a004.
3. Jean-Pierre Schirmann, Paul Bourdauducq "Hydrazine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a13_177.
4. Ottersen, T.; Hope, H. "The Structure and Electron Deformation Density Distribution of Carbonohydrazide (Carbohydrazide) at 85 K" Acta Crystallographica B 1979, volume 35, p373-p378. doi:10.1107/S0567740879003575
5. Buecker, Brad (1997). Power Plant Water Chemistry A Practical Guide. PennWell Publishing Company. pp. 13–16. ISBN 0-87814-619-9.
6. "Patent US4269717". Retrieved 8 October 2012.
7. "Patent US2970899". Retrieved 8 October 2012.
8. "MSDS". Retrieved 8 October 2012.