4-氰基-1H-1,2,3-三唑-5-甲酰胺 | 57613-19-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 4-氰基-1H-1,2,3-三唑-5-甲酰胺
• 英文名称: 5-cyano-2H-[1,2,3]triazole-4-carboxylic acid amide
• 英文别名: 4-carboxamide-5-cyano-2H-1,2,3-triazole；4-Cyano-1H-1,2,3-triazole-5-carboxamide；5-cyano-2H-triazole-4-carboxamide
• CAS: 57613-19-1
• 化学式: C₄H₃N₅O
• mdl: MFCD19216256
• 分子量: 137.101
• InChiKey: NYMNVVMHCRPLTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  4

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  2H-1,2,3-三唑-4,5-二甲酰胺	2H-[1,2,3]triazole-4,5-dicarboxylic acid diamide	388623-87-8	C4H5N5O2	155.116

反应信息

• 作为反应物：
  描述：

  4-氰基-1H-1,2,3-三唑-5-甲酰胺 在 盐酸 、 溶剂黄146 作用下， 反应 1.0h， 以85%的产率得到2H-1,2,3-三唑-4,5-二甲酰胺
  参考文献：
  名称：

  Novel 2H-1,2,3-Triazole sodium complex from N-[2-amino-1,2-dicyanovinyl]alkanamides

  摘要：

  Diazotization at 0 degrees C of N-[2-amino-1,2-dicyanovinyl]ethanamide 2a or propanamide 2b prepared from diaminomaleonitrile (DAMN) I using aqueous acetic acid and NaNO2 solution furnished sodium complex 3. The X-ray structure of the complex 3 showed that it is a 1:1 mixture of the neutral 2H-triazole heterocycle 4ii and its anion deprotonated at the central (N) atom of the ring, together with a sodium counter ion and two coordinated water molecules. However, when the diazotization reaction was carried out in the presence of aqueous HCl, the product was 5-cyano-2H-[1,2,3]triazole-4-carboxylic acid amide monohydrate 4ii. Diazotization of DAMN 1 using aqueous HCl furnished 1H-1,2,3-triazole-4,5-dicarbonitrile 5, whereas with acetic acid there was no reaction, and hence no route analogous to that leading to complex 3. The structure of both complex 3 and the triazole monohydrate 4ii were solved using X-ray crystallography, and the compounds under study were fully characterized using spectroscopic techniques.

  DOI：

  10.1016/s0385-5414(07)81094-x
• 作为产物：
  描述：

  N-((Z)-2-amino-1,2-dicyanoethenyl)acetamide 在 盐酸 、 sodium nitrite 作用下， 生成 4-氰基-1H-1,2,3-三唑-5-甲酰胺
  参考文献：
  名称：

  Novel 2H-1,2,3-Triazole sodium complex from N-[2-amino-1,2-dicyanovinyl]alkanamides

  摘要：

  Diazotization at 0 degrees C of N-[2-amino-1,2-dicyanovinyl]ethanamide 2a or propanamide 2b prepared from diaminomaleonitrile (DAMN) I using aqueous acetic acid and NaNO2 solution furnished sodium complex 3. The X-ray structure of the complex 3 showed that it is a 1:1 mixture of the neutral 2H-triazole heterocycle 4ii and its anion deprotonated at the central (N) atom of the ring, together with a sodium counter ion and two coordinated water molecules. However, when the diazotization reaction was carried out in the presence of aqueous HCl, the product was 5-cyano-2H-[1,2,3]triazole-4-carboxylic acid amide monohydrate 4ii. Diazotization of DAMN 1 using aqueous HCl furnished 1H-1,2,3-triazole-4,5-dicarbonitrile 5, whereas with acetic acid there was no reaction, and hence no route analogous to that leading to complex 3. The structure of both complex 3 and the triazole monohydrate 4ii were solved using X-ray crystallography, and the compounds under study were fully characterized using spectroscopic techniques.

  DOI：

  10.1016/s0385-5414(07)81094-x

文献信息

• The nitrogen-rich energetic compound 4-carboxamide-5-(1H-tetrazol-5-yl)-1H-1,2,3-triazole and its 1D sodium complex: synthesis and properties
  作者：Jian Qin、Tong Li、Jian-Guo Zhang、Zhi-Bin Zhang

  DOI：10.1039/c6ra22151c

  日期：——

  5-yl)-1H-1,2,3-triazole (2) and its sodium complex (3) have been synthesized using diaminomaleodinitrile as the starting material in a three step synthesis. Both of the compounds were comprehensively characterized using Fourier transform-infrared spectroscopy (FT-IR), mass spectrometry (MS) and elemental analysis (EA). The sodium complex of 4-carboxamide-5-(1H-tetrazol-5-yl)-1H-1,2,3-triazole was confirmed

  以二氨基马来腈为原料合成了新型的富氮高能化合物4-羧酰胺-5-（1 H-四唑-5-基）-1 H -1,2,3-三唑（2）及其钠配合物（3）。三步合成中的起始原料。两种化合物均使用傅里叶变换红外光谱（FT-IR），质谱（MS）和元素分析（EA）进行了全面表征。4-羧酰胺-5-（1 H-四唑-5-基）-1 H的钠配合物首次使用单晶X射线衍射确认了-1,1,2,3-三唑。两种化合物的热稳定性已使用差示扫描量热法（DSC）测量，表明分解峰温度为332.6°C（2）和374.1°C（3）。用高斯09计算2的密度和形成焓，并用Kamlet-Jacobs方程预测爆炸压力（21.9 GPa）和爆炸速度（7182 ms -1）。化合物2对撞击（> 40 J）或摩擦（> 360 N）不敏感。
• 295. Studies on hydrogen cyanide. Part X. The tetrapolymer
  作者：L. E. Hinkel、G. O. Richards、O. Thomas

  DOI：10.1039/jr9370001432

  日期：——
• Novel 2H-1,2,3-Triazole sodium complex from N-[2-amino-1,2-dicyanovinyl]alkanamides
  作者：A ALAZMI、P GEORGE、O ELDUSOUQUI

  DOI：10.1016/s0385-5414(07)81094-x

  日期：2007.10.1

  Diazotization at 0 degrees C of N-[2-amino-1,2-dicyanovinyl]ethanamide 2a or propanamide 2b prepared from diaminomaleonitrile (DAMN) I using aqueous acetic acid and NaNO2 solution furnished sodium complex 3. The X-ray structure of the complex 3 showed that it is a 1:1 mixture of the neutral 2H-triazole heterocycle 4ii and its anion deprotonated at the central (N) atom of the ring, together with a sodium counter ion and two coordinated water molecules. However, when the diazotization reaction was carried out in the presence of aqueous HCl, the product was 5-cyano-2H-[1,2,3]triazole-4-carboxylic acid amide monohydrate 4ii. Diazotization of DAMN 1 using aqueous HCl furnished 1H-1,2,3-triazole-4,5-dicarbonitrile 5, whereas with acetic acid there was no reaction, and hence no route analogous to that leading to complex 3. The structure of both complex 3 and the triazole monohydrate 4ii were solved using X-ray crystallography, and the compounds under study were fully characterized using spectroscopic techniques.