2165-21-1

Usage

Physical form

white crystalline substance

Solubility

soluble in water

Odor

amine-like

Common uses

reagent in organic synthesis, preparation of pharmaceuticals, agrochemicals, and dyes

Other uses

ligand in coordination chemistry, stabilizer in propellants and explosives

Stability

relatively stable

Handling

can be handled safely under normal laboratory conditions

InChI:InChI=1/CH4N6/c2-1-4-5-6-7(1)3/h3H2,(H2,2,4,6)

Upstream product

• 79-19-6 thiosemicarbazide 
• 64-17-5 ethanol 
• 764-05-6 cyanogen azide 
• 136369-04-5 5-aminotetrazole potassium salt 
• 506-68-3 bromocyane 
• 1314927-50-8 CH₄N₆*ClH 

Downstream Products

• 133414-92-3 8-Phenyl-6-p-tolyl-8,9-dihydro-7H-tetrazolo[1,5-b][1,2,4]triazepine 
• 145181-96-0 [1-(4-Fluoro-phenyl)-meth-(E)-ylidene]-(5-imino-4,5-dihydro-tetrazol-1-yl)-amine 
• 126256-55-1 N¹-[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-tetrazole-1,5-diamine 
• 133414-94-5 6-(4-Nitro-phenyl)-8-phenyl-8,9-dihydro-7H-tetrazolo[1,5-b][1,2,4]triazepine 
• 133414-91-2 5,7-diphenyl-5,6-dihydro-4H-tetrazolo<1,5-b>-1,2,4-triazepine 
• 59318-31-9 6,7-dimethyl-tetrazolo[1,5-b][1,2,4]triazine 
• 133414-96-7 8-(4-Chloro-phenyl)-6-phenyl-8,9-dihydro-7H-tetrazolo[1,5-b][1,2,4]triazepine 
• 133414-95-6 6-Phenyl-8-p-tolyl-8,9-dihydro-7H-tetrazolo[1,5-b][1,2,4]triazepine 
• 133414-93-4 6-(4-Methoxy-phenyl)-8-phenyl-8,9-dihydro-7H-tetrazolo[1,5-b][1,2,4]triazepine 
• 2762-35-8 5,6-Diphenyl-tetrazolo<1,5-b>as-triazin 
• 1418005-61-4 1,4,5-triaminotetrazolium tosylate 
• 329710-24-9 1,2,3,3a,4,10-hexaaza-cyclopenta[b]fluoren-9-one 

Relevant academic research and scientific papers

Synthesis, performance, and thermal behavior of a novel insensitive EDNA/DAT Co-crystal

Due to the acidity and the limited applications of 1,4-dinitro-1,4-diazabutane (EDNA), a novel nitrogen rich energetic co-crystal based on EDNA and 1,5-diaminotetrazole (DAT) in a 1:2 molar ratio was synthesized. The formation of the co-crystal was tested by scanning electron microscope (SEM), powder X-ray diffraction (PXRD) and Raman spectroscopy. Based on the elemental analysis and the enthalpy of combustion obtained by the calorimetric bomb, the enthalpy of formation was calculated to be 196.9 kJ·mol–1. Sensitivity to impact was measured and 50 % probability of initiation was 9.7 J for the co-crystal. In addition, the detonation characteristics were predicted by EXPLO5 Code. The detonation velocity (D) and the detonation pres-sure (P) of the co-crystal are 8254.5 m·s–1 and 26.7 GPa, respectively. The thermal behavior and decomposition kinetics of the co-crystal and the coformer were described using nonisothermal differential scanning calorimetry (DSC) and thermogravimetry/differential thermogravimetry (TG/DTG) techniques. There is an obvious difference between the thermal behavior of the co-crystal and the coformer. The activation energy of the co-crystal (125.3 kJ·mol–1) is lower than the coformer. The obtained co-crystal has high nitrogen content and acceptable sensitivity to external stimuli, which makes it promising for expanding the reuse of EDNA in ammunition after overcomeing its acidity problem.

Synthesis, Structure, and Energetic Properties of 1,5-Diaminotetrazolium Sulfate Salts

1,5-diaminotetrazolium chloride (DATC) and 1,5-diaminotetrazolium sulfate (DATS) were synthesized in this work. The structures of DATS and DATC were characterized. The single crystal of DATS was first cultured, and its structure was analyzed. The thermal behavior of DATS was investigated. The activation energy and pro-exponential factor were calculated, Ek = 120.86 KJ/mol, Ak = 1012.96 s-1. The density, heat of formation, detonation pressure, and detonation velocity of DATS were first calculated. The detonation pressure and detonation velocity of DATS are P = 11.877 GPa, D = 5.617 km s-1, which are smaller than those of 1,5-diaminotetrazolium nitrate (DATN) (P = 33.3GPa, D = 8.77 km s-1).

Pressure-induced phase transition of 1,5-diamino-1: H -tetrazole (DAT) under high pressure

Nitrogen-rich energetic materials have attracted certain interest as promising high energy density materials (HEDMs) in recent years. Pure N2 and nitrogen-based molecular crystals are ideal HEDMs that would polymerize under high pressure, as reported in previous literature. We selected a 1,5-diamino-1H-tetrazole (DAT) crystal, which has two kinds of molecular structures and hydrogen bonds, to study under high pressure by spectroscopy and diffraction due to its high nitrogen percentage and low sensitivities. Pressure-induced structure transitions occur at pressures of 2.3-6.6 GPa, ～8.5 GPa, and ～17.7 GPa. The phase transition at 2.3-6.6 GPa is related to the rotation of NH2, and the latter two transitions are caused by both the rotation of NH2 and the distortion of the heterocycle. Significantly, the reconstitution of the hydrogen bond may induce the rotation/distortion of the NH2/heterocycle in the second phase transition. There is no evidence showing a transformation between the two molecular structures in the whole pressure range studied. Our investigation uncovers the phase transition mechanism of DAT under pressure, which will help to find targeted HEDMs. This journal is

SYNTHESIS AND PROPERTIES OF 1,5-DIAMINOTETRAZOLE

An effective method was developed for preparation of 1,5-diaminotetrazole from thiosemicarbazide and sodium azide in the presence of lead(II) oxide and ammonium chloride in DMFA.Its physical properties and certain reactions were studied.

Synthesis and characterization of a novel energetic complex [Cd(DAT) 6](NO3)2 (DAT = 1,5-diamino-tetrazole) with high nitrogen content

The novel high nitrogen-containing energetic complex [Cd(DAT) 6](NO3)2was synthesized by reaction of Cd(NO3)2·6H2O with 1,5-diamino-tetrazole (DAT). It was characterized by elemental analysis, FT-IR spectroscopy and single-crystal X-ray diffraction, analysis. The central Cd2+ ion is coordinated by six nitrogen atoms from six DAT ligand molecules to form a hexacoordinate distorted octahedral compound. The [Cd(DAT)6](NO 3)2 molecules are linked together through two types of hydrogen bonds thus forming a stable three-dimensional net structure. The thermal decomposition mechanism of [Cd(DAT)6](NO3) 2 was investigated by DSC and TG/DTG analyses and FT-IR spectroscopy. The kinetic parameters of the exothermic process were studied by using Kissinger's and Ozawa-Doyle's methods.

Energetic 1,5-diamino-4H-tetrazolium nitro-substituted azolates

1,5-Diaminotetrazole (DAT) is a fascinating component in the construction of high-energy-density materials because of its extremely high nitrogen content (～84%). Three DAT nitro-substituted azolate salts were synthesized and fully characterized by IR, NMR, elemental analysis, thermal stability, phase behavior, and density. 1,5-Diamino-4H-tetrazolium 5-nitrotetrazolate salt (2) crystallizes in the orthorhombic system Pbca. The detonation pressure (P) values calculated for these salts range from 28.05 to 29.88 GPa, and the detonation velocities (D) from 8343 to 8655 m s-1, which make them competitive energetic materials. Each of the compounds has an oxygen balance approaching zero (-23.8 to -33.5%). Their impact sensitivities were determined. The salts were compared using natural bond orbital (NBO) analysis of the nitro-substituted azolate anions. These CHNO-explosives, DAT nitro-substituted azolate salts, are potential green energetic materials which are obtained via a straightforward synthetic route. The Royal Society of Chemistry.

Energetic nitrogen-rich derivatives of 1,5-diaminotetrazole

High-energy-density materials can be obtained by reaction of monosubstituted hydrazines with cyanogen azide to generate 1,5-diaminotetrazole derivatives. Azidohydrazones are postulated as intermediates in this reaction (see scheme). (Chemical Equation Pre

Heteropolycyclic inhibitors of protein kinases

A compound of the formula wherein, independently at each occurrence, v, w, and x are selected from C, N, O, and S, with H substitution as needed to fulfill open valence sites; y and z are selected from N and C, with H substitution as needed to fulfill open valence sites, with the proviso that each of w, v, x, y and z is not simultaneously C; the ring formed from v, w, x, y and z may be saturated or unsaturated; and R1, R2, R3and R4are selected from hydrogen, alkyl, aryl, alkaryl, aralkyl, heteroalkyl, and heteroaryl; wherein any adjacent two of R1, R2, R3and R4may join together to form a 5, 6 or 7-membered carbocyclic or heterocyclic ring, with the proviso that each of R1, R2, R3and R4is not simultaneously hydrogen. Pharmaceutical compositions of said compounds, and methods of use in the treatment of biological conditions including cellular hyperproliferation, are disclosed.

Heteropolycyclic inhibitors of protein kinases

A compound of the formula wherein, independently at each occurrence, v, w, and x are selected from C, N, O, and S, with H substitution as needed to fulfill open valence sites; y and z are selected from N and C, with H substitution as needed to fulfill open valence sites, with the proviso that each of w, v, x, y and z is not simultaneously C; the ring formed from v, w, x, y and z may be saturated or unsaturated; and R1, R2, R3 and R4 are selected from hydrogen, alkyl, aryl, alkaryl, aralkyl, heteroalkyl, and heteroaryl; wherein any adjacent two of R1, R2, R3 and R4 may join together to form a 5, 6 or 7-membered carbocyclic or heterocyclic ring, with the proviso that each of R1, R2, R3 and R4 is not simultaneously hydrogen. Pharmaceutical compositions of said compounds, and methods of use in the treatment of biological conditions including cellular hyperproliferation, are disclosed.