15284-29-4

Basic information

• Product Name: 2-(5-amino-1H-tetrazol-1-yl)ethanol
• CAS NO: 15284-29-4
• Molecular Formula: C₃H₇N₅O
• Molecular Weight: 129.1206
• Mol File: 15284-29-4.mol

Chemical Properties

• Boiling Point: 391.3°C at 760 mmHg
• Flash Point: 190.5°C
• Density: 1.81g/cm³
• Vapor Pressure: 7.95E-07mmHg at 25°C
• Refractive Index: 1.775
• CAS DataBase Reference: 2-(5-amino-1H-tetrazol-1-yl)ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(5-amino-1H-tetrazol-1-yl)ethanol(15284-29-4)
• EPA Substance Registry System: 2-(5-amino-1H-tetrazol-1-yl)ethanol(15284-29-4)

Safety Data

• Hazardous Substances Data: 15284-29-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(5-amino-1H-tetrazol-1-yl)ethanol is utilized as a key intermediate in the synthesis of various drugs. Its unique structure and reactivity make it a valuable component in the development of pharmaceuticals with specific therapeutic properties.
Used in Organic Chemistry:
As a reagent, 2-(5-amino-1H-tetrazol-1-yl)ethanol plays a significant role in organic chemistry, facilitating various chemical reactions and contributing to the synthesis of complex organic molecules.
Used in Explosives and Propellants Industry:
Due to its energetic properties, 2-(5-amino-1H-tetrazol-1-yl)ethanol has potential applications in the field of explosives and propellants. Its ability to release energy makes it a candidate for use in formulations that require high energy output.

Upstream product

• 107-07-3 2-chloro-ethanol 
• 15454-56-5 5-amino-1H-tetrazole sodium salt 
• 141-43-5 ethanolamine 
• 4418-61-5 5-aminotetrazole 
• 764-05-6 cyanogen azide 

Downstream Products

• 15284-31-8 1-(2-chloroethyl)-5-aminotetrazole 
• 145181-95-9 2-(5-{[1-Phenyl-meth-(E)-ylidene]-amino}-tetrazol-1-yl)-ethanol 

Relevant articles and documents

1-Nitratoethyl-5-nitriminotetrazole derivatives - Shaping future high explosives

1-(2-Nitratoethyl)-5-nitriminotetrazole (2) was formed by the reaction of 1-(2-hydroxyethyl-5-aminotetrazole (1) and 100% HNO3. Compound 1 was obtained by alkylation of 5-amino-1H-tetrazole. Next to the known byproduct 1-(2-hydroxyethyl)-5-nitr

New energetic materials: Functionalized 1-ethyl-5-aminotetrazoles and 1-ethyl-5-nitriminotetrazoles

Alkylation of 5-aminotetra-zole (1) with 2-chloroethanol leads to a mixture of the N-1 and N-2 isomers of (2-hydroxyethyl)-5-aminotetrazole. Treatment of 1-(2-hydroxyethyl)-5-ami-notetrazole (2) with SOCl2 yielded 1-(2-chlorethyl)-5-aminotetrazole (3). 1-(2-Azidoethyl)-5-aminotetrazole (4) was generated by the reaction of 3 with sodium azide. Nitration of 2, 3, and 4 with HNO3 (100%) yielded in the case of 2 and 3 1-(2-hydroxyethyl)-5- nitrimi-notetrazole (5) and 1-(2-chloroethyl)-5-nitriminotetrazole (6). In the case of 4, 1-(2-nitratoethyl)-5-nitriminotetrazole monohydrate (7) was obtained. 1-(2-Azidoethyl)-5-nitriminotetrazole (8) could be obtained by nitration of 4 with NO2BF4 via the formation of potassium 1-(2-azidoethyl)-5-nitriminote-trazolate (9). The reaction of 6 with NaN 3 resulted in the formation of the salt sodium 1-(2-chloroethyl)-5- nitrimi-notetrazolate (10 a). The deprotonation reaction of 6 was further investigated by the formation of the ammonium salt (10 b). The protonation of 2 and 4 with dilute nitric acid led to 1-(2-hydrox-yethyl)-5-aminotetrazolium nitrate (11) and 1-(2-azidoethyl)-5-aminotetrazoli-um nitrate (12), respectively. Similarly, protonation of 4 with perchloric acid led to 1-(2-azidoethyl)-5-aminotetrazo-lium perchlorate monohydrate (13). Since 5-nitrimino-tetrazoles can be used as bidentate ligands, the coordination abilities of 5, 6, and 8 were tested by the reaction with copper nitrate tri-hydrate, yielding the copper complexes ans-[diaquabis{1-(2-hydroxyethyl)-5- nitriminotetrazolato-κ2N4,O5}copper(II)] (14), trans-[diaquabis{1-(2-chloroethyl)-5-nitriminotetrazolato- κ2N4,O5}copper(II)] dihydrate (15), and [diaquabis{1-(2-azidoethyl)-5-nitrimino-tetrazolato-κ2N 4,O5}copper(II)] (16). All compounds were characterized by low-temperature single-crystal X-ray diffraction. In addition, comprehensive characterization (IR, Raman, and mul-tinuclear NMR spectroscopy (1H, 13C), elemental analysis, mass spectrometry, DSC) was performed. The heats of formation of selected compounds were computed by using heats of combustion obtained by bomb calorimetry or calculated by the atomization method. With these values and the densities determined from X-ray crystallography, several detonation parameter were calculated by the EXPLO5 program. Finally, the sensitivities towards impact and friction were determined using a BAM drop hammer and friction tester.

Energetic nitrogen-rich salts of 1-(2-hydroxyethyl)-5-nitriminotetrazole

1-(2-Hydroxyethyl)-5-nitriminotetrazole (2) was formed by the reaction of 5-amino-1-(2-hydroxyethyl)tetrazole (1) and 100 % HNO3. Compound 1 was obtained by alkylation of 5-amino-1H-tetrazole with 2-chloroethanol. Nitrogen-rich salts such as the ammonium (3), hydroxylammonium (4), guanidinium (5), aminoguanidinium (6), diaminoguanidinium (7), triaminoguanidinium (8), azidoformamidinium (9), and diaminouronium (10) 1-(2-hydroxyethyl)-5- nitriminotetrazolate were prepared by deprotonation or metathesis reactions. Compounds 3-10 were fully characterized by single-crystal X-ray diffraction (except for 9 and 10), vibrational spectroscopy (IR and Raman), multinuclear NMR spectroscopy, elemental analysis, and differential scanning calorimetry (DSC) measurements. The heats of formation of 4-10 were calculated by the atomization method based on CBS-4M enthalpies. With these values and the X-ray densities, several detonation parameters such as the detonation pressure, velocity, energy, and temperature were computed using the EXPLO5 code. In addition their sensitivities towards impact, friction, and electrical discharge were tested using a BAM drophammer, a friction tester, and a small-scale electrical discharge device. Copyright

Energetic N-trinitroethyl-substituted mono-, Di-, and triaminotetrazoles

A series of dense energetic N-trinitroethyl-substituted mono-, bis-, and tri-5-aminotetrazoles were obtained by reacting primary amines with in situ generated cyanogen azide, followed by the trinitroethyl functionalization that involves a condensation of a hydroxymethyl intermediate (prepared by a reaction with formaldehyde) with trinitromethane. These compounds were fully characterized by using multinuclear NMR spectroscopy, IR, elemental analysis, differential scanning calorimetry (DSC), and, in one case with 9, with single-crystal XRD analysis. The heats of formation for all compounds were calculated with Gaussian 03 and then combined with experimental densities to determine the detonation pressures (P) and velocities (Dv) of the energetic materials. Interestingly, most of them exhibited high density, good thermal stability, acceptable oxygen balance, positive heat of formation, low impact sensitivity, and excellent detonation properties, which highlighted their practical application potentials as a fascinating class of highly energetic materials.

Energetic mono-, di-, and trisubstituted nitroiminotetrazoles

(Chemical Equation Presented) A bundle of energy: The title compounds were synthesized in good yield from aminotetrazoles (obtained from the reaction of cyanogen azide with primary amines) by treatment with 100% nitric acid and were fully characterized by

1-Substituted 5-aminotetrazoles: Syntheses from CNN3 with primary amines

(Chemical Equation Presented) 1-Substituted 5-aminotetrazoles were prepared in situ by an excellent reaction of cyanogen azide and primary amines to generate an imidoyl azide as an intermediate in acetonitrile/water. After cyclization, the intermediate ga