疊氮化氰
疊氮化氰, 化學式 N3CN 或 CN4, 是一種疊氮化合物，外觀為無色油狀液體。[1] 它是一種容易爆炸的化合物，可溶於多種有機溶劑，一般疊氮化氰都是這樣操作的。[1][2][3]在1960年代早期，杜邦公司的 F.D. Marsh 首次合成了疊氮化氰。[1][4]
| 疊氮化氰 | |
|---|---|
| |
| IUPAC名 Carbononitridic azide | |
| 別名 | 氰化疊氮 |
| 識別 | |
| CAS號 | 764-05-6 
|
| PubChem | 136583 |
| SMILES |
|
| InChI |
|
| InChIKey | KWEDUNSJJZVRKR-UHFFFAOYSA-N |
| 性質 | |
| 化學式 | CN4 |
| 摩爾質量 | 68.04 g·mol−1 |
| 外觀 | 無色油狀液體 |
| 若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。 | |
疊氮化氰是一種炸藥，儘管它對於炸藥的實際應用來說太不穩定了，並且在稀溶液中也是極其危險的。[5][6]它在化學上的用途是作為原位製備的試劑，用於在稀釋溶液中或減壓下以化學形式合成二氨基四唑等化學藥品。[7][8][9][10][11][12][13] 疊氮化氰可以由疊氮化鈉和氯化氰[1]或溴化氰,[4]在乙腈溶液里反應而成。該反應必須小心進行，因為會產生微量對衝擊敏感的副產物。[4][11]
參考資料
- ^ 1.0 1.1 1.2 1.3 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, Derek. Cyanogen azide. 2001. ISBN 978-0471936237. doi:10.1002/047084289X.rc268.
|journal=被忽略 (幫助) - ^ 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. （原始內容存檔於2020-09-22）.
- ^ 4.0 4.1 4.2 Marsh, F. D. Cyanogen azide. The Journal of Organic Chemistry. September 1972, 37 (19): 2966–2969. doi:10.1021/jo00984a012.
- ^ Robert Matyáš; Jiří Pachman. Primary Explosives. Springer Science & Business Media. 12 March 2013: 111 [2020-07-01]. ISBN 978-3-642-28436-6. （原始內容存檔於2022-04-08）.
- ^ 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. （原始內容存檔於2020-09-22）.
- ^ Gordon W. Gribble; J. Joule. Progress in Heterocyclic Chemistry. Elsevier. 3 September 2009: 250–1. ISBN 978-0-08-096516-1.
- ^ 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.
- ^ Barry M. Trost. Oxidation. Elsevier. 1991: 479 [2020-07-01]. ISBN 978-0-08-040598-8. （原始內容存檔於2020-09-22）.
- ^ Lowe, Derek. Things I Won't Work With: Cyanogen Azide. Science Translational Medicine. American Association for the Advancement of Science. [27 April 2017]. （原始內容存檔於2020-07-02）.
- ^ 11.0 11.1 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.
- ^ 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. Plenum Press. : 68–9. ISBN 9780306370762.