Azomethane

Azomethane
Names
IUPAC name
Dimethyldiazene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.211.415 Edit this at Wikidata
EC Number
  • 685-709-9
  • InChI=1S/C2H6N2/c1-3-4-2/h1-2H3
    Key: JCCAVOLDXDEODY-UHFFFAOYSA-N
  • CN=NC
Properties
C2H6N2
Molar mass 58.084 g·mol−1
Appearance colourless to pale yellow gas[1]
Melting point −78 °C (trans)[2]
−66 °C (cis)[2]
Boiling point 1.5 °C (trans)[2]
95 °C (cis)[2]
Hazards
GHS labelling:[3]
GHS02: Flammable
Danger
H220
P203, P210, P222, P280, P377, P381, P403, P410+P403
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Azomethane is an organic compound with the chemical formula CH3-N=N-CH3. It exhibits cis-trans isomerism. It can be produced by the reaction of 1,2-dimethylhydrazine dihydrochloride with copper(II) chloride in sodium acetate solution. The reaction produces the azomethane complex of copper(I) chloride, which can produce free azomethane by thermal decomposition.[4] It is the source of methyl radical in laboratory.[5]

CH3-N=N-CH3 → 2 CH3· + N2
  1. ^ Azomethan Lexikon der Chemie
  2. ^ a b c d Ackermann, Martin N.; Craig, Norman C.; Isberg, Ralph R.; Lauter, David M.; MacPhail, Richard A.; Young, William G. (1977). "cis-Dimethyldiazene". Journal of the American Chemical Society. 99 (5): 1661–1663. doi:10.1021/ja00447a072. ISSN 0002-7863.
  3. ^ "Azomethane". pubchem.ncbi.nlm.nih.gov.
  4. ^ Francis P. Jahn (September 1937). "The Preparation of Azomethane". Journal of the American Chemical Society. 59 (9): 1761–1762. doi:10.1021/ja01288a502. ISSN 0002-7863. Archived from the original on 2022-10-23. Retrieved 2022-10-23.
  5. ^ Zhai, Run-Sheng; Chan, Yuet Loy; Chuang, Ping; Hsu, Chien-Kui; Mukherjee, Manabendra; Chuang, Tung J.; Klauser, Ruth (2004-04-01). "Chemisorption and Reaction Characteristics of Methyl Radicals on Cu(110)". Langmuir: The ACS Journal of Surfaces and Colloids. 20 (9): 3623–3631. doi:10.1021/la036294u. ISSN 0743-7463. PMID 15875392.