Azomethane Explained

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.^[1] It is the source of methyl radical in laboratory.^[2]

CH₃-N=N-CH₃ → 2 CH₃· + N₂

Further reading

• Computational and Theoretical Chemistry. 1203. en. September 2021. 113344. 10.1016/j.comptc.2021.113344. Energetic azo compounds based on 2,2′, 4,4′, 6,6′- hexanitroazobenzene: Structures, detonation performance, and sensitivity. 2022-10-23. Jianying Zhang, Gangling Chen, Xuedong Gong.
• Inorganic Chemistry. 55. 21. en. 0020-1669. 2016-11-07. 10947–10954. 10.1021/acs.inorgchem.6b01488. Oxidative Addition of π-Bonds and σ-Bonds to an Al(I) Center: The Second-Order Carbene Property of the AlNacNac Compound. 2022-10-23. Wolfgang W. Schoeller, Guido D. Frey. 27739674 . 2022-10-01. https://web.archive.org/web/20221001212029/https://pubs.acs.org/doi/10.1021/acs.inorgchem.6b01488. live.

Notes and References

1. Journal of the American Chemical Society. 59. 9. en. 0002-7863. September 1937. 1761–1762. 10.1021/ja01288a502. The Preparation of Azomethane. 2022-10-23. Francis P. Jahn. 2022-10-23. https://web.archive.org/web/20221023115638/https://pubs.acs.org/doi/abs/10.1021/ja01288a502. live.
2. Zhai . Run-Sheng . Chan . Yuet Loy . Chuang . Ping . Hsu . Chien-Kui . Mukherjee . Manabendra . Chuang . Tung J. . Klauser . Ruth . Chemisorption and Reaction Characteristics of Methyl Radicals on Cu(110) . Langmuir: The ACS Journal of Surfaces and Colloids . 20 . 9 . 2004-04-01 . 0743-7463 . 15875392 . 10.1021/la036294u . 3623–3631.