叠氮乙酸乙酯

叠氮乙酸乙酯是一种有机化合物,化学式为C4H7N3O2。它可以溴乙酸乙酯叠氮化钠为原料反应制得。[1]它和苯乙炔在催化下反应,可以得到4-苯基-1H-1,2,3-三唑-1-乙酸乙酯;[3]它和乙酰腈加压反应,可以得到5-乙酰基-1H-四唑-1-乙酸乙酯。[4]它在50%甲醇水溶液中用氢氧化锂水解,再酸化后可以得到叠氮乙酸。[5]

叠氮乙酸乙酯
识别
CAS号 637-81-0  checkY
PubChem 69480
SMILES
 
  • CCOC(=O)CN=[N+]=[N-]
InChI
 
  • 1S/C4H7N3O2/c1-2-9-4(8)3-6-7-5/h2-3H2,1H3
InChIKey HVJJYOAPXBPQQV-UHFFFAOYSA-N
性质
化学式 C4H7N3O2
摩尔质量 129.12 g·mol−1
密度 1.1181 g·cm-3(25 °C)[1]
沸点 74—75 °C(347—348 K)(23 mmHg)[1]
164 °C(437 K)(760 mmHg)[2]
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

参考文献

  1. Huber, W. Frederick. . Journal of the American Chemical Society (American Chemical Society (ACS)). 1955, 77 (1): 112–116. ISSN 0002-7863. doi:10.1021/ja01606a036.
  2. Swetha, M.; Ramana, P. Venkata; Shirodkar, S. G. . Organic Preparations and Procedures International (Informa UK Limited). 2011, 43 (4): 348–353. ISSN 0030-4948. doi:10.1080/00304948.2011.594002.
  3. Díaz Velázquez, Heriberto; Ruiz García, Yara; Vandichel, Matthias; Madder, Annemieke; Verpoort, Francis. . Org. Biomol. Chem. (Royal Society of Chemistry (RSC)). 2014, 12 (46): 9350–9356. ISSN 1477-0520. doi:10.1039/c4ob01350f.
  4. Zavarzin, I. V.; Zhulin, V. M.; Yarovenko, V. N.; Krayushkin, M. M. Synthesis of 5-acyltetrazoles under high pressure(俄文). Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1988. (5): 1168-1170
  5. Valverde, Ibai E.; Bauman, Andreas; Kluba, Christiane A.; Vomstein, Sandra; Walter, Martin A.; Mindt, Thomas L. . Angewandte Chemie International Edition (Wiley). 2013-07-05, 52 (34): 8957–8960. ISSN 1433-7851. doi:10.1002/anie.201303108.
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