叠氮化氰

叠氮化氰
	IUPAC名; Carbononitridic azide
别名	氰化叠氮
识别
CAS号	764-05-6
PubChem	136583
SMILES	C(#N)N=[N+]=[N-];
InChI	1S/CN4/c2-1-4-5-3;
InChIKey	KWEDUNSJJZVRKR-UHFFFAOYSA-N
性质
化学式	CN4
摩尔质量	68.04 g·mol−1
外观	无色油状液体
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

叠氮化氰, 化学式 N₃CN 或 CN₄, 是一种叠氮化合物，外观为无色油状液体。^[1] 它是一种容易爆炸的化合物，可溶于多种有机溶剂，一般叠氮化氰都是这样操作的。^[1]^[2]^[3]在1960年代早期，杜邦公司的 F.D. Marsh 首次合成了叠氮化氰。^[1]^[4]

Quick Facts 叠氮化氰, 识别 ...

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叠氮化氰是一种炸药，尽管它对于炸药的实际应用来说太不稳定了，并且在稀溶液中也是极其危险的。^[5]^[6]它在化学上的用途是作为原位制备的试剂，用于在稀释溶液中或减压下以化学形式合成二氨基四唑等化学药品。^[7]^[8]^[9]^[10]^[11]^[12]^[13] 叠氮化氰可以由叠氮化钠和氯化氰^[1]或溴化氰,^[4]在乙腈溶液里反应而成。该反应必须小心进行，因为会产生微量对冲击敏感的副产物。^[4]^[11]

参考资料

[1]
Marsh, F. D.; Hermes, M. E. Cyanogen Azide. Journal of the American Chemical Society. October 1964, 86 (20): 4506–4507. doi:10.1021/ja01074a071.
[2]
Goldsmith, Derek. Cyanogen azide. 2001. ISBN 978-0471936237. doi:10.1002/047084289X.rc268. |journal=被忽略 (帮助)
[3]
Houben-Weyl Methods of Organic Chemistry Vol. E 21e, 4th Edition Supplement: Stereoselective Synthesis: Bond Formation, C-N, C-O, C-P, C-S, C-Se, C-Si, C-Sn, C-Te. Thieme. 14 May 2014: 5414 [2020-07-01]. ISBN 978-3-13-182284-0. （原始内容存档于2020-09-22）.
[4]
Marsh, F. D. Cyanogen azide. The Journal of Organic Chemistry. September 1972, 37 (19): 2966–2969. doi:10.1021/jo00984a012.
[5]
Robert Matyáš; Jiří Pachman. Primary Explosives. Springer Science & Business Media. 12 March 2013: 111 [2020-07-01]. ISBN 978-3-642-28436-6. （原始内容存档于2022-04-08）.
[6]
Michael L. Madigan. First Responders Handbook: An Introduction, Second Edition. CRC Press. 13 September 2017: 170 [2020-07-01]. ISBN 978-1-351-61207-4. （原始内容存档于2020-09-22）.
[7]
Gordon W. Gribble; J. Joule. Progress in Heterocyclic Chemistry. Elsevier. 3 September 2009: 250–1. ISBN 978-0-08-096516-1.
[8]
Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 17: Six-Membered Hetarenes with Two Unlike or More than Two Heteroatoms and Fully Unsaturated Larger-Ring Heterocycles. Thieme. 14 May 2014: 2082. ISBN 978-3-13-178081-2.
[9]
Barry M. Trost. Oxidation. Elsevier. 1991: 479 [2020-07-01]. ISBN 978-0-08-040598-8. （原始内容存档于2020-09-22）.
[10]
Lowe, Derek. Things I Won't Work With: Cyanogen Azide. Science Translational Medicine. American Association for the Advancement of Science. [27 April 2017]. （原始内容存档于2020-07-02）.
[11]
Joo, Young-Hyuk; Twamley, Brendan; Garg, Sonali; Shreeve, Jean'ne M. Energetic Nitrogen-Rich Derivatives of 1,5-Diaminotetrazole. Angewandte Chemie International Edition. 4 August 2008, 47 (33): 6236–6239. PMID 18615414. doi:10.1002/anie.200801886.
[12]
Audran, Gérard; Adiche, Chiaa; Brémond, Paul; El Abed, Douniazad; Hamadouche, Mohammed; Siri, Didier; Santelli, Maurice. Cycloaddition of sulfonyl azides and cyanogen azide to enamines. Quantum-chemical calculations concerning the spontaneous rearrangement of the adduct into ring-contracted amidines. Tetrahedron Letters. March 2017, 58 (10): 945–948. doi:10.1016/j.tetlet.2017.01.081.
[13]
Energetic Materials, Volume 1. Plenum Press. : 68–9. ISBN 9780306370762.

外部链接

NIST（页面存档备份，存于互联网档案馆）

[Marsh_1964-1] [1]
Marsh, F. D.; Hermes, M. E. Cyanogen Azide. Journal of the American Chemical Society. October 1964, 86 (20): 4506–4507. doi:10.1021/ja01074a071.

[Goldsmith-2] [2]
Goldsmith, Derek. Cyanogen azide. 2001. ISBN 978-0471936237. doi:10.1002/047084289X.rc268. |journal=被忽略 (帮助)

[3] [3]
Houben-Weyl Methods of Organic Chemistry Vol. E 21e, 4th Edition Supplement: Stereoselective Synthesis: Bond Formation, C-N, C-O, C-P, C-S, C-Se, C-Si, C-Sn, C-Te. Thieme. 14 May 2014: 5414 [2020-07-01]. ISBN 978-3-13-182284-0. （原始内容存档于2020-09-22）.

[1972_Marsh-4] [4]
Marsh, F. D. Cyanogen azide. The Journal of Organic Chemistry. September 1972, 37 (19): 2966–2969. doi:10.1021/jo00984a012.

[MatyášPachman2013-5] [5]
Robert Matyáš; Jiří Pachman. Primary Explosives. Springer Science & Business Media. 12 March 2013: 111 [2020-07-01]. ISBN 978-3-642-28436-6. （原始内容存档于2022-04-08）.

[Madigan2017-6] [6]
Michael L. Madigan. First Responders Handbook: An Introduction, Second Edition. CRC Press. 13 September 2017: 170 [2020-07-01]. ISBN 978-1-351-61207-4. （原始内容存档于2020-09-22）.

[GribbleJoule2009-7] [7]
Gordon W. Gribble; J. Joule. Progress in Heterocyclic Chemistry. Elsevier. 3 September 2009: 250–1. ISBN 978-0-08-096516-1.

[8] [8]
Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 17: Six-Membered Hetarenes with Two Unlike or More than Two Heteroatoms and Fully Unsaturated Larger-Ring Heterocycles. Thieme. 14 May 2014: 2082. ISBN 978-3-13-178081-2.

[Trost1991-9] [9]
Barry M. Trost. Oxidation. Elsevier. 1991: 479 [2020-07-01]. ISBN 978-0-08-040598-8. （原始内容存档于2020-09-22）.

[Things_I_Won’t_Work_With:_Cyanogen_Azide-10] [10]
Lowe, Derek. Things I Won't Work With: Cyanogen Azide. Science Translational Medicine. American Association for the Advancement of Science. [27 April 2017]. （原始内容存档于2020-07-02）.

[Energetic_Nitrogen-Rich_Derivatives_of_1,5-Diaminotetrazole-11] [11]
Joo, Young-Hyuk; Twamley, Brendan; Garg, Sonali; Shreeve, Jean'ne M. Energetic Nitrogen-Rich Derivatives of 1,5-Diaminotetrazole. Angewandte Chemie International Edition. 4 August 2008, 47 (33): 6236–6239. PMID 18615414. doi:10.1002/anie.200801886.

[Cycloaddition_of_sulfonyl_azides_and_cyanogen_azide_to_enamines._Quantum-chemical_calculations_concerning_the_spontaneous_rearrangement_of_the_adduct_into_ring-contracted_amidines-12] [12]
Audran, Gérard; Adiche, Chiaa; Brémond, Paul; El Abed, Douniazad; Hamadouche, Mohammed; Siri, Didier; Santelli, Maurice. Cycloaddition of sulfonyl azides and cyanogen azide to enamines. Quantum-chemical calculations concerning the spontaneous rearrangement of the adduct into ring-contracted amidines. Tetrahedron Letters. March 2017, 58 (10): 945–948. doi:10.1016/j.tetlet.2017.01.081.

[Energetic_Materials,_Volume_1-13] [13]
Energetic Materials, Volume 1. Plenum Press. : 68–9. ISBN 9780306370762.

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