63666-11-5

Basic information

• Product Name: ethyl 5-amino-2H-1,2,4-triazole-3-carboxylate
• Synonyms: ethyl 5-amino-2H-1,2,4-triazole-3-carboxylate;ETHYL 5-AMINO-4H-[1,2,4]TRIAZOLE-3-CARBOXYLATE;3-amino-1H-1,2,4-triazole-5-carboxylic acid ethyl ester;ethyl 3-amino-1H-1,2,4-triazole-5-carboxylate;ethyl 3-azanyl-1H-1,2,4-triazole-5-carboxylate;5-AMino-4H-[1,2,4]triazole-3-carboxylic acid ethyl ester;NSC 148474
• CAS NO: 63666-11-5
• Molecular Formula: C₅H₈N₄O₂
• Molecular Weight: 156.15
• EINECS: 675-026-4
• Mol File: 63666-11-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 242-243℃
• Boiling Point: 373.9 °C at 760 mmHg
• Flash Point: 179.9 °C
• Appearance: /
• Density: 1.408
• Vapor Pressure: 8.68E-06mmHg at 25°C
• Refractive Index: 1.591
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 8.92±0.40(Predicted)
• CAS DataBase Reference: ethyl 5-amino-2H-1,2,4-triazole-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 5-amino-2H-1,2,4-triazole-3-carboxylate(63666-11-5)
• EPA Substance Registry System: ethyl 5-amino-2H-1,2,4-triazole-3-carboxylate(63666-11-5)

Safety Data

• Hazardous Substances Data: 63666-11-5(Hazardous Substances Data)

Usage

General Description

Ethyl 5-amino-2H-1,2,4-triazole-3-carboxylate is an organic compound with the molecular formula C6H8N4O2. It is a derivative of 1,2,4-triazole, which is a five-membered heterocyclic compound containing three nitrogen atoms and two carbon atoms. The compound is commonly used as a building block in the synthesis of various pharmaceuticals and agrochemicals. Its ethyl ester group provides stability and solubility in organic solvents, making it suitable for use in organic synthesis. Additionally, the presence of the amino and carboxylate functional groups makes it a versatile molecule for the formation of bonds with other compounds, allowing for the creation of diverse chemical structures with varied properties and applications.

InChI:InChI=1/C5H8N4O2/c1-2-11-4(10)3-7-5(6)9-8-3/h2H2,1H3,(H3,6,7,8,9)

Upstream product

• 3641-13-2 5-amino-1H-[1,2,4]triazole-3-carboxylic acid 
• 64-17-5 ethanol 
• 3641-13-2 5-amino-4H-1,2,4-triazole-3-carboxylic acid 

Downstream Products

• 1234620-74-6 (rac)-diethyl 7-(4-cyanophenyl)-5-methyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-2,6-dicarboxylate 
• 1234620-36-0 (rac)-diethyl 7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-2,6-dicarboxylate 
• 683782-57-2 ethyl 5-acetamido-1H-1,2,4-triazole-3-carboxylate 
• 921225-14-1 (5-amino-4H-1,2,4-triazol-3-yl)(pyrrolidin-1-yl)methanone 
• 114040-29-8 ethyl 5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylate 
• 60016-63-9 5-amino-1H-1,2,4-triazole-3-carboxamide 

Relevant articles and documents

5-Amino-1: H-1,2,4-triazole-3-carbohydrazide and its applications in the synthesis of energetic salts: A new strategy for constructing the nitrogen-rich cation based on the energetic moiety combination

Nitrogen-rich cation 5-amino-1H-1,2,4-triazole-3-carbohydrazide and its derivatives were synthesized by a new molecular design strategy based on the energetic moiety combination. All derivatives were fully characterized by vibrational spectroscopy (IR), multinuclear (1H, 13C) NMR spectroscopy, elemental analysis, differential scanning calorimetry (DSC), and impact and friction-sensitivity tests. The structures of compounds 1-4, 7 and 8 were further confirmed by single-crystal X-ray diffraction and six different types of crystal packing were surprisingly discovered. The results show that the extensive hydrogen bonding interactions between the cations and anions lead to a complex 3D network, which contribute greatly to the high density, insensitivity and thermal stability of the 5-amino-1H-1,2,4-triazole-3-carbohydrazide salts. It is also found that the cationic form of 5-amino-1H-1,2,4-triazole-3-carbohydrazide can decrease the sensitivity and elevate the nitrogen content of the target salts effectively. Some of these salts exhibit reasonable physical properties, such as good thermal stability (up to 407 °C) and reasonable impact sensitivities (IS = 5-80 J). In addition, theoretical detonation properties of the energetic salts obtained with EXPLO 5 (version 6.02) confirm them as competitively energetic compounds comparable to those of RDX or HMX.

Synthesis and characterization of 5-(1,2,4-Triazol-3-yl)tetrazoles with various energetic functionalities

In this contribution the synthesis and full structural as well as spectroscopic characterization of three 5-(1,2,4-triazol-3-yl)tetrazoles along with selected energetic moieties like nitro, nitrimino, and azido groups are presented. The main goal is a comparative study on the influence of those variable energetic moieties on structural and energetic properties. A complete characterization including IR and Raman as well as multinuclear NMR spectroscopy of all compounds is presented. Additionally, X-ray crystallographic measurements were performed and reveal insights into structural characteristics as well as inter- and intramolecular interactions. The standard enthalpies of formation were calculated for all compounds at the CBS-4M level of theory and reveal high positive heats of formation for all compounds. The calculated detonation parameters (using the EXPLO5.05 program) are in the range of 8000 m s-1 (8097 m s-1 (5), 8020 m s-1 (6), 7874 m s-1 (7)). As expected, the measured impact and friction sensitivities as well as decomposition temperatures strongly depend on the energetic moiety at the triazole ring. The C-C connection of a triazole ring with its opportunity to introduce a large variety of energetic moieties and a tetrazole ring, implying a large energy content, leads to the selective synthesis of primary and secondary explosives.

AZO METAL CHELATE DYE AND OPTICAL RECORDING MEDIUM

To provide a dye to be used for an optical recording medium excellent in both high speed recording characteristics and reproduction durability. A dye having an azo compound represented by the following formula coordinated to a metal ion: wherein the ring