Azomethane
{{Chembox
| Name =
| ImageFile = (Z)-Azomethane.svg
| ImageFile2 = (E)-Azomethane.svg
| IUPACName = Dimethyldiazene
| OtherNames =
| Section1 = {{Chembox Identifiers
| CASNo = 503-28-6
| CASNo_Ref = {{cascite|correct|CAS}}
| ChemSpiderID = 9992
| EC_number = 685-709-9
| PubChem = 10421
| StdInChI=1S/C2H6N2/c1-3-4-2/h1-2H3
| StdInChIKey = JCCAVOLDXDEODY-UHFFFAOYSA-N
| SMILES = CN=NC }}
| Section2 = {{Chembox Properties
| C=2 | H=6 | N=2
| Appearance = colourless to pale yellow gas[http://www.wissenschaft-online.de/abo/lexikon/chemie/882 Azomethan] Lexikon der Chemie
| Density=
| MeltingPt= −78 °C (trans){{cite journal | last1=Ackermann | first1=Martin N. | last2=Craig | first2=Norman C. | last3=Isberg | first3=Ralph R. | last4=Lauter | first4=David M. | last5=MacPhail | first5=Richard A. | last6=Young | first6=William G. | title=cis-Dimethyldiazene | journal=Journal of the American Chemical Society | volume=99 | issue=5 | year=1977 | issn=0002-7863 | doi=10.1021/ja00447a072 | pages=1661–1663}}
−66 °C (cis)
| BoilingPt = 1.5 °C (trans)
95 °C (cis)
| Solubility = }}
| Section3 = {{Chembox Hazards
| GHSPictograms = {{GHS02}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|220}}
| PPhrases = {{P-phrases|203|210|222|280|377|381|403|410+403}}
| MainHazards =
| FlashPt =
}}
}}
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.{{cite journal|journal=Journal of the American Chemical Society|volume=59|issue=9|language=en|issn=0002-7863|date=September 1937|pages=1761–1762|doi=10.1021/ja01288a502|url=https://pubs.acs.org/doi/abs/10.1021/ja01288a502|title=The Preparation of Azomethane|accessdate=2022-10-23|author=Francis P. Jahn|archive-date=2022-10-23|archive-url=https://web.archive.org/web/20221023115638/https://pubs.acs.org/doi/abs/10.1021/ja01288a502|url-status=live|url-access=subscription}} It is the source of methyl radical in laboratory.{{cite journal | last1=Zhai | first1=Run-Sheng | last2=Chan | first2=Yuet Loy | last3=Chuang | first3=Ping | last4=Hsu | first4=Chien-Kui | last5=Mukherjee | first5=Manabendra | last6=Chuang | first6=Tung J. | last7=Klauser | first7=Ruth | title=Chemisorption and Reaction Characteristics of Methyl Radicals on Cu(110) | journal=Langmuir: The ACS Journal of Surfaces and Colloids | volume=20 | issue=9 | date=2004-04-01 | issn=0743-7463 | pmid=15875392 | doi=10.1021/la036294u | pages=3623–3631}}
:CH3-N=N-CH3 → 2 CH3· + N2
References
{{reflist}}
Further reading
- {{cite journal|journal=Computational and Theoretical Chemistry|volume=1203|language=en|date=September 2021|pages=113344|doi=10.1016/j.comptc.2021.113344|url=https://linkinghub.elsevier.com/retrieve/pii/S2210271X21002024|title=Energetic azo compounds based on 2,2′, 4,4′, 6,6′- hexanitroazobenzene: Structures, detonation performance, and sensitivity|accessdate=2022-10-23|author=Jianying Zhang, Gangling Chen, Xuedong Gong|url-access=subscription}}
- {{cite journal|journal=Inorganic Chemistry|volume=55|issue=21|language=en|issn=0020-1669|date=2016-11-07|pages=10947–10954|doi=10.1021/acs.inorgchem.6b01488|url=https://pubs.acs.org/doi/10.1021/acs.inorgchem.6b01488|title=Oxidative Addition of π-Bonds and σ-Bonds to an Al(I) Center: The Second-Order Carbene Property of the AlNacNac Compound|accessdate=2022-10-23|author=Wolfgang W. Schoeller, Guido D. Frey|pmid=27739674 |archive-date=2022-10-01|archive-url=https://web.archive.org/web/20221001212029/https://pubs.acs.org/doi/10.1021/acs.inorgchem.6b01488|url-status=live|url-access=subscription}}