Formylhydrazine

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Formylhydrazine
Names
Preferred IUPAC name
Formohydrazide[1]
Other names
Formic hydrazide
Identifiers
3D model (JSmol)
635759
ChemSpider
ECHA InfoCard 100.009.880 Edit this at Wikidata
EC Number
  • 210-867-9
RTECS number
  • LQ8615000
UNII
  • InChI=1S/CH4N2O/c2-3-1-4/h1H,2H2,(H,3,4)
    Key: XZBIXDPGRMLSTC-UHFFFAOYSA-N
  • C(=O)NN
Properties
CH4N2O
Molar mass 60.056 g·mol−1
Melting point 54 °C (129 °F; 327 K)
yes
Solubility ethanol
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335, H336
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).

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

  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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