Formylhydrazine

Formylhydrazine
Names
	Preferred IUPAC name Formohydrazide
	Other names Formic hydrazide
Identifiers
CAS Number	624-84-0;
3D model (JSmol)	Interactive image;
Beilstein Reference	635759
ChemSpider	11728;
ECHA InfoCard	100.009.880
EC Number	210-867-9;
PubChem CID	12229;
RTECS number	LQ8615000;
UNII	V1D8X13QFN;
CompTox Dashboard (EPA)	DTXSID6020642 ;
	InChI InChI=1S/CH4N2O/c2-3-1-4/h1H,2H2,(H,3,4) Key: XZBIXDPGRMLSTC-UHFFFAOYSA-N;
	SMILES C(=O)NN;
Properties
Chemical formula	CH4N2O
Molar mass	60.056 g·mol−1
Melting point	54 °C (129 °F; 327 K)
Solubility in water	yes
Solubility	ethanol
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335, H336
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Related compounds
Related compounds	acetyl hydrazine, benzoyl hydrazine, diformyl hydrazine, N-methyl-N-formylhydrazine
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Formylhydrazine is a chemical compound with the molecular formula CH₄N₂O and it has a mass of 60 g/mol. It is also known as formic acid hydrazide, hydrazinecarboxaldehyde, formohydrazide, or formic hydrazide. It is one of the simplest compounds in the hydrazide class. Formylhydrazine can act as a bidentate ligand with cobalt, zinc,^[2] or cadmium.^[3]

This is also an isomer of urea in the sense of which the hydrogen atom on the amine group has transferred to the carbonyl group.

Formation

Formylhydrazine can be produced by the acid hydrolysis of diazomethane. H₂CN₂ + H₂O → HC(O)NHNH₂.^[4]

Properties

Formylhydrazine causes lung cancer in mice.^[5]

References

^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 872. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
^ Srinivasan, Krishnan; Govindarajan, Subbaiah; Harrison, William T.A. (July 2009). "Divalent metal complexes of formylhydrazine: Syntheses and crystal structures of M(CH₄N₂O)₂(H₂O)₂·2NO₃ (M=Zn, Co)". Inorganic Chemistry Communications. 12 (7): 619–621. doi:10.1016/j.inoche.2009.05.002.
^ Kharitonov, Yu Ya; Machkhoshvili, R. I.; Metreveli, D. P.; Pirtshalava, N. I. (1977). "Complex compounds of nitrates and thiocyanates of metals with formyl hydrazine". Koordinatsionnaya Khimiya (in Russian). 3 (6): 897–901.
^ Müller, Eugen (2013). Neuere Anschauungen der Organischen Chemie: Organische Chemie für Fortgeschrittene (in German). Springer-Verlag. p. 453. ISBN 978-3-642-87591-5.
^ Arcos, Joseph C.; Woo, Yin-Tak; Argus, Mary F. (2013). Aliphatic Carcinogens: Structural Bases and Biological Mechanisms. Elsevier. p. 367. ISBN 978-1-4832-6372-4.

[1] International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 872. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.

[2] Srinivasan, Krishnan; Govindarajan, Subbaiah; Harrison, William T.A. (July 2009). "Divalent metal complexes of formylhydrazine: Syntheses and crystal structures of M(CH₄N₂O)₂(H₂O)₂·2NO₃ (M=Zn, Co)". Inorganic Chemistry Communications. 12 (7): 619–621. doi:10.1016/j.inoche.2009.05.002.

[3] Kharitonov, Yu Ya; Machkhoshvili, R. I.; Metreveli, D. P.; Pirtshalava, N. I. (1977). "Complex compounds of nitrates and thiocyanates of metals with formyl hydrazine". Koordinatsionnaya Khimiya (in Russian). 3 (6): 897–901.

[4] Müller, Eugen (2013). Neuere Anschauungen der Organischen Chemie: Organische Chemie für Fortgeschrittene (in German). Springer-Verlag. p. 453. ISBN 978-3-642-87591-5.

[5] Arcos, Joseph C.; Woo, Yin-Tak; Argus, Mary F. (2013). Aliphatic Carcinogens: Structural Bases and Biological Mechanisms. Elsevier. p. 367. ISBN 978-1-4832-6372-4.

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