叠氮甲烷

叠氮甲烷
别名	甲基叠氮化物
识别
CAS号	624-90-8
PubChem	79079
ChemSpider	71411
SMILES	[N-]=[N+]=N\C;
性质
化学式	CH3N3
摩尔质量	57.05 g·mol⁻¹
爆炸性
撞击感度	高
摩擦感度	高
危险性
主要危害	有害，易爆炸
相关物质
相关化学品	叠氮酸、叠氮化氯、叠氮乙烷
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

叠氮甲烷（CH₃N₃）是烷基叠氮化物（英语：Alkyl azides）的一种，它们都属于叠氮酸的共价型衍生物。叠氮甲烷是一种直线型分子。根据共振式，中间的氮原子的两对成键电子显然是直线形排列的，但与甲基相连的氮原子却有三对孤对电子：H₃C-N=N⁺=N^- ⇔ H₃C-N^--N⁺≡N 。^[1]

Quick Facts 叠氮甲烷, 识别 ...

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它可以由叠氮化钠的甲基化反应制得。该物质最早于1905年制得。^[2] 它以如下的一级反应分解：CH₃N₃ → CH₃N + N₂。^[3]

无生源论认为，叠氮甲烷可能是在星际冰中由高能银河宇宙射线和光子合成分子的前体之一。^[4]

安全措施

叠氮甲烷在常温时稳定但加热时可能爆炸。^[5] 汞的存在将增加它对震动和火花的敏感度。它与丙二酸二甲酯、甲醇钠、汞、甲醇、叠氮化钠、硫酸二甲酯、氢氧化钠、叠氮酸不能共存。加热分解时产生有毒的氮氧化物气体。^{[来源请求]}它可以在-80℃的黑暗中无限期储存。^[6]

参考资料

[1]
Pauling, Linus, Brockway, O.; The Adjacent Charge Rule and the Structure of Methyl Azide, Methyl nitrate, and Fluorine nitrate; JACS, 1937, 59 (1), pp 13-20 DOI:10.1021/ja01280a005
[2]
Dimroth, O. and Wislicenus, W.; Chemische Berichte ; 38, 1573 (1905)
[3]
O'Dell, M.S. and Darwent B. Thermal decomposition of methyl azide （页面存档备份，存于互联网档案馆）Canadian Journal of Chemistry, 48, 1140 (1970)
[4]
Alfredo Quinto-Hernandez and Alec M. Wodtke, Department of Chemistry and Biochemistry, University of California, Santa Barbara; Chris J. Bennett, Y. Seol Kim, and Ralf I. Kaiser; Department of Chemistry, University of Hawaii at Manoa; On the Interaction of Methyl Azide (CH3N3) Ices with Ionizing Radiation: Formation of Methanimine (CH2NH), Hydrogen Cyanide (HCN), and Hydrogen Isocyanide (HNC) （页面存档备份，存于互联网档案馆） ; Journal of Physical Chemistry DOI: 10.1021/jp103028v Publication Date (Web): December 17, 2010
[5]
Bretherick's handbook of reactive chemical hazards; edited by P. G. Urben
[6]
Chae, Junghyun, Methyl Azide, John Wiley & Sons, Ltd (编), Encyclopedia of Reagents for Organic Synthesis, Chichester, UK: John Wiley & Sons, Ltd: rn00795, 2008-03-14, ISBN 978-0-471-93623-7, doi:10.1002/047084289x.rn00795 （英语）

Graner, G., Hirota, E., Iijima, T., Kuchitsu, K., Ramsay,D. A., Vogt, J., Vogt,N.: CH3N3 Methyl azide. Kuchitsu, K. (ed.). SpringerMaterials - The Landolt-Börnstein Database [1] DOI: 10.1007/10653318_320
NIST Webbook （页面存档备份，存于互联网档案馆）

[1] [1]
Pauling, Linus, Brockway, O.; The Adjacent Charge Rule and the Structure of Methyl Azide, Methyl nitrate, and Fluorine nitrate; JACS, 1937, 59 (1), pp 13-20 DOI:10.1021/ja01280a005

[2] [2]
Dimroth, O. and Wislicenus, W.; Chemische Berichte ; 38, 1573 (1905)

[3] [3]
O'Dell, M.S. and Darwent B. Thermal decomposition of methyl azide （页面存档备份，存于互联网档案馆）Canadian Journal of Chemistry, 48, 1140 (1970)

[4] [4]
Alfredo Quinto-Hernandez and Alec M. Wodtke, Department of Chemistry and Biochemistry, University of California, Santa Barbara; Chris J. Bennett, Y. Seol Kim, and Ralf I. Kaiser; Department of Chemistry, University of Hawaii at Manoa; On the Interaction of Methyl Azide (CH3N3) Ices with Ionizing Radiation: Formation of Methanimine (CH2NH), Hydrogen Cyanide (HCN), and Hydrogen Isocyanide (HNC) （页面存档备份，存于互联网档案馆） ; Journal of Physical Chemistry DOI: 10.1021/jp103028v Publication Date (Web): December 17, 2010

[5] [5]
Bretherick's handbook of reactive chemical hazards; edited by P. G. Urben

[e-EROS-6] [6]
Chae, Junghyun, Methyl Azide, John Wiley & Sons, Ltd (编), Encyclopedia of Reagents for Organic Synthesis, Chichester, UK: John Wiley & Sons, Ltd: rn00795, 2008-03-14, ISBN 978-0-471-93623-7, doi:10.1002/047084289x.rn00795 （英语）

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