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Carbohydrazide
Names
	IUPAC name 1,3-Diaminourea
	Other names Carbohydrazine
Identifiers
CAS Number	497-18-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:61308 ;
ChemSpider	66578 ;
ECHA InfoCard	100.007.126
EC Number	207-837-2;
PubChem CID	73948;
UNII	W8V7FYY4WH ;
CompTox Dashboard (EPA)	DTXSID5038757 ;
	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 O=C(NN)NN;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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.

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: carbohydrazide 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]
Jet fuel: carbohydrazine can be used as a component in jet fuels, as a large amount of heat is being produced when the material is burned.
Carbohydrazide has been used to develop ammunition propellants,^[7] stabilize soaps,^[2] and is used as a reagent in organic synthesis.
Salts of carbohydrazide, such as nitrate, dinitrate and perchlorate, can be used as secondary explosives.^[8] Complex salts of carbohydrazide, like bis(carbohydrazide)diperchloratocopper(II) and tris(carbohydrazide)nickel(II) perchlorate, can be used as primary explosives in laser detonators.^[9]

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.^[10]

References

^ Inorganic Syntheses Volume IV. McGraw-Hill Book Company, Inc. 1953. p. 35. ISBN 9780470132678.
^ ^a ^b ^c ^d ^e ^f Kurzer, Frederick; Michael Wilkinson (February 1970). "Chemistry of carbohydrazide and thiocarbohydrazide". Chemical Reviews. 70 (1): 111–149. doi:10.1021/cr60263a004. PMID 4391877.
^ Jean-Pierre Schirmann, Paul Bourdauducq "Hydrazine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a13_177.
^ 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
^ Buecker, Brad (1997). Power Plant Water Chemistry A Practical Guide. PennWell Publishing Company. pp. 13–16. ISBN 978-0-87814-619-2.
^ "Patent US4269717". Retrieved 8 October 2012.
^ "Patent US2970899". Retrieved 8 October 2012.
^ Fischer, Niko; Klapötke, Thomas M.; Stierstorfer, Jörg (June 2011). "Explosives Based on Diaminourea". Propellants, Explosives, Pyrotechnics. 36 (3): 225–232. doi:10.1002/prep.201100001. S2CID 97871632.
^ Joas, Manuel; Klapötke, Thomas M. (April 2015). "Laser Initiation of Tris(carbohydrazide)metal(II) Perchlorates and Bis(carbohydrazide)diperchloratocopper(II)". Propellants, Explosives, Pyrotechnics. 40 (2): 246–252. doi:10.1002/prep.201400142.
^ "MSDS". Retrieved 8 October 2012.