30169-21-2

Basic information

• Product Name: 3,6-BIS(3,5-DIMETHYL-1H-PYRAZOL-1-YL)-1,2-DIHYDRO-1,2,4,5-TETRAAZINE
• Synonyms: 3,6-BIS(3,5-DIMETHYL-1H-PYRAZOL-1-YL)-1,2-DIHYDRO-1,2,4,5-TETRAAZINE
• CAS NO: 30169-21-2
• Molecular Formula: C₁₂H₁₆N₈
• Molecular Weight: 272.31
• Mol File: 30169-21-2.mol
• Article Data: 18

Chemical Properties

• Melting Point: 150 °C
• Boiling Point: 449.7±55.0 °C(Predicted)
• Appearance: /
• Density: 1.45±0.1 g/cm3(Predicted)
• PKA: 1.74±0.19(Predicted)
• CAS DataBase Reference: 3,6-BIS(3,5-DIMETHYL-1H-PYRAZOL-1-YL)-1,2-DIHYDRO-1,2,4,5-TETRAAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-BIS(3,5-DIMETHYL-1H-PYRAZOL-1-YL)-1,2-DIHYDRO-1,2,4,5-TETRAAZINE(30169-21-2)
• EPA Substance Registry System: 3,6-BIS(3,5-DIMETHYL-1H-PYRAZOL-1-YL)-1,2-DIHYDRO-1,2,4,5-TETRAAZINE(30169-21-2)

Safety Data

• Hazardous Substances Data: 30169-21-2(Hazardous Substances Data)

Usage

Description

3,6-BIS(3,5-DIMETHYL-1H-PYRAZOL-1-YL)-1,2-DIHYDRO-1,2,4,5-TETRAAZINE is a nitrogen-rich organic compound characterized by its unique tetrazine ring structure and two pyrazole moieties. It is known for its potential applications in various fields due to its chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
3,6-BIS(3,5-DIMETHYL-1H-PYRAZOL-1-YL)-1,2-DIHYDRO-1,2,4,5-TETRAAZINE is used as a key intermediate in the synthesis of 3-arylamino-6-benzylamino-1,2,4,5-tetrazines, which possess antimalarial activities. Its role in the development of new antimalarial drugs is significant, as it contributes to the creation of compounds that can effectively combat malaria-causing parasites.
Used in Chemical Research:
In the field of chemical research, 3,6-BIS(3,5-DIMETHYL-1H-PYRAZOL-1-YL)-1,2-DIHYDRO-1,2,4,5-TETRAAZINE is used to prepare 3,3''-azobis(6-amino-1,2,4,5-tetrazine) DAAT, a nitrogen-rich compound with potential applications in various chemical reactions and processes. Its unique structure and properties make it a valuable compound for exploring new chemical pathways and synthesizing novel materials.

Upstream product

• 4000-16-2 1,2,3-triaminoguanidinium nitrate 
• 123-54-6 acetylacetone 
• 5329-29-3 triaminoguanidine hydrochloride 
• 30169-25-6 3,6-bis-(3,5-dimethyl-pyrazol-1-yl)-1,2,4,5-tetrazine 
• 79-06-1 2-propenamide 
• 2203-24-9 N,N',N''-triaminoguanidine 
• 1522-20-9 acetylacetone 
• 50-01-1 guanidine hydrochloride 
• 109-72-8 n-butyllithium 
• 106-95-6 allyl bromide 
• 120-72-9 indole 

Downstream Products

• 67-51-6 3,5-dimethyl-1H-pyrazole 
• 114720-64-8 6-(3,5-dimethyl-pyrazol-1-yl)-2H-[1,2,4,5]tetrazin-3-one 
• 30169-25-6 3,6-bis-(3,5-dimethyl-pyrazol-1-yl)-1,2,4,5-tetrazine 

Relevant articles and documents

Syntheses and crystal structures of two unsymmetrical 1,2,4, 5-tetrazine derivatives

Two unsymmetrical 1,2,4,5-tetrazine derivatives, (6-(3,5-dimethyl-1H- pyrazol-1-yl)-1,2,4,5-tetrazin-3-ylamino) methanol (C9H 13N7O, 3) and 4-(6-(3,5-dimethyl-1H-pyrazol- 1-yl)-1,2,4,5-tetrazin-3-yl) morpholine (C11H15N 7O, 4), were synthesized from 3,6-bis(3,5-dimethyl-1H-pyrazol-1- yl)-1,2,4,5-tetrazine and the corresponding aliphatic amine (2-aminoethanol and morpholine, respectively), there structureswere confirmed by single-crystalX-ray diffractionmethods. Both molecules have very similar bond length and angle patterns, The crystal structures show that compound 3 is stabilized by intermolecular O-H-N, N-H-O hydrogen bonds and p-p interactions, while compound 4 is stabilized by π- π interactions. The structure analyses establish that compound 3 belongs to the monoclinic system, space group P2(1)/c, with crystal data a = 6.979(2) A, b = 9.563(3) A, c = 16.542(5) A, V = 1084.4(5) A3, Z = 4, F(000) = 496, R1 = 0.0488, wR2 = 0.1063. Compound 4 belongs to the orthorhombic system, space group P2(1)2(1)2(1), with crystal data a = 6.544(14) A, b = 12.085(3) A, c = 15.753(4) A, V = 1245.7(5) A3, Z = 4, F(000) = 552, R1 = 0.0403, wR2 = 0.0913. Springer Science+Business Media, LLC 2012.

Proposed Proton-Transfer Mechanism for the Initial Decomposition Steps of BTATz

The first steps in the gas-phase decomposition mechanism of N3,N6-bis (1H-tetrazol-5-yl)-1,2,4,5-tetrazine-3,6-diamine, BTATz, anions and the kinetic isotope effects in these processes were studied using combined multi-stage mass spectrometry (MS/MS) and computational techniques. Two major fragmenta-tion processes, the exergonic loss of nitrogen molecules and the endergonic loss of hydrazoic acid, were identified. The observation of a primary isotope effect supported by calculations, suggests that the loss of a nitrogen molecule from the tetrazole ring involves proton migration, either to, or within the terazole ring, as a rate-determining step. The fragmentation of a hydrazoic acid occurs through an asymmetrical retro pericyclic reaction. Calculations show the relevance of these mechanisms to neutral BTATz. Our findings may contribute to the understanding of decomposition routes in these nitrogen-rich energetic materials and allow tailoring their reactivity and decomposition pathways for better control of performance.

The crystal structure and synthesis mechanism of 3,6-Bis(3,5- dimethylpyrazol-1-yl)-1,4-dihydro-1,2,4,5-tetrazine (BDT): A key precursor of s-tetrazine

The single crystal structure of 1,1′-bis (3,5-dimethyl-pyrazole) methenehydrazine (BDM) was determined by X-ray single crystal diffraction for the first time. The obtained experimental results indicated that BDM was the intermediate of 3,6-bis(3,5-dimethylpyrazol-1-yl)-1,4-dihydro-1,2,4,5-tetrazine (BDT), which was the key precursor of s-tetrazine. By this evidence, the preparation mechanism of BDT was proved: At 318.15 K, triaminoguanidine and pentanedione reacted to achieve the intermediate (BDM) by molecular nucleophilic addition and intramolecular nucleophilic substitution; when heated to 363.15 K, BDT was then generated by two molecules of BDM with nucleophilic substitution reaction. Furthermore, the thermal decomposition properties and also the non-isothermal kinetic parameters have been investigated in the present work.

Nucleophilic Attack on Nitrogen in Tetrazines by Silyl-Enol Ethers

The nucleophilic addition of silyl-enol ethers to nitrogen in 3-monosubstituted s-tetrazines mediated by BF3 is reported. The preference for this azaphilic addition over the usually observed inverse electron demand Diels-Alder reactions was evaluated theoretically and corroborated by experiments. The substrate dependency of this unusual reaction was rationalized by determination of the activation barriers and on the basis of the activation strain model by employing density functional theory.

Hydrogen sulfide fluorescent probe as well as preparation method and application thereof

The invention provides a series of hydrogen sulfide fluorescent probe compounds and a preparation method thereof. A fluorescent probe can be used for detecting hydrogen sulfide and has very good selectivity for the hydrogen sulfide; when being mixed in a water solution or a buffer solution, the fluorescent probe can be used for detecting in vitro hydrogen sulfide. The fluorescent probe compounds can autonomously penetrate cell membranes into cells, and can be used for intracellular hydrogen sulfide imaging.