Azomethane

Azomethane

Names
IUPAC name Dimethyldiazene
Identifiers
CAS Number	503-28-6  Y
3D model (JSmol)	Interactive image
ChemSpider	9992
ECHA InfoCard	100.211.415
EC Number	685-709-9
PubChem CID	10421
CompTox Dashboard (EPA)	DTXSID70870570
InChI InChI=1S/C2H6N2/c1-3-4-2/h1-2H3 Key: JCCAVOLDXDEODY-UHFFFAOYSA-N
SMILES CN=NC
Properties
Chemical formula	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]
Pictograms
Signal word	Danger
Hazard statements	H220
Precautionary statements	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). Infobox references

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

References

1. Azomethan Lexikon der Chemie
2. 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.

Further reading

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