53876-70-3

Basic information

• Product Name: 3,6-BIS(4-CHLOROPHENOYL)-1,2-DIHYDRO-1,2,4,5 TETRAZINE
• Synonyms: 3,6-BIS(4-CHLOROPHENOYL)-1,2-DIHYDRO-1,2,4,5 TETRAZINE;Chlorophenoyl dihydro tetrazine
• CAS NO: 53876-70-3
• Molecular Formula: C₁₄H₁₀Cl₂N₄
• Molecular Weight: 305.16
• Mol File: 53876-70-3.mol

Chemical Properties

• Melting Point: 252 °C(Solv: 1-butanol (71-36-3))
• Boiling Point: 413 °C at 760 mmHg
• Flash Point: 203.6 °C
• Appearance: /
• Density: 1.45 g/cm³
• Vapor Pressure: 4.98E-07mmHg at 25°C
• Refractive Index: 1.696
• PKA: 2.81±0.20(Predicted)
• CAS DataBase Reference: 3,6-BIS(4-CHLOROPHENOYL)-1,2-DIHYDRO-1,2,4,5 TETRAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-BIS(4-CHLOROPHENOYL)-1,2-DIHYDRO-1,2,4,5 TETRAZINE(53876-70-3)
• EPA Substance Registry System: 3,6-BIS(4-CHLOROPHENOYL)-1,2-DIHYDRO-1,2,4,5 TETRAZINE(53876-70-3)

Safety Data

• Hazardous Substances Data: 53876-70-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Research and Organic Synthesis:
3,6-BIS(4-CHLOROPHENOYL)-1,2-DIHYDRO-1,2,4,5 TETRAZINE is used as a reagent for its high reactivity, enabling the synthesis of various complex organic compounds and contributing to the advancement of chemical research.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 3,6-BIS(4-CHLOROPHENOYL)-1,2-DIHYDRO-1,2,4,5 TETRAZINE is used as a key intermediate in the development of new drugs, owing to its unique chemical properties and potential for creating novel therapeutic agents.
Used in Dye Production:
3,6-BIS(4-CHLOROPHENOYL)-1,2-DIHYDRO-1,2,4,5 TETRAZINE is utilized as a building block in the production of dyes, where its chemical structure contributes to the creation of dyes with specific color properties and stability.
Used in Polymer Production:
In the polymer industry, 3,6-BIS(4-CHLOROPHENOYL)-1,2-DIHYDRO-1,2,4,5 TETRAZINE is used as a monomer or a component in the synthesis of polymers, which can be tailored for specific applications such as plastics, coatings, or fibers.
Safety Precautions:
It is important to handle 3,6-BIS(4-CHLOROPHENOYL)-1,2-DIHYDRO-1,2,4,5 TETRAZINE with care, as it may be harmful if ingested or inhaled and can cause skin and eye irritation. Proper safety measures should be taken during its use and storage to minimize potential health risks.

InChI:InChI=1/C14H10Cl2N4/c15-11-5-1-9(2-6-11)13-17-19-14(20-18-13)10-3-7-12(16)8-4-10/h1-8H,(H,17,18)(H,19,20)

Upstream product

• 37932-51-7 1,4-dichloro-1,4-bis(4-chlorophenyl)-2,3-diazabutadiene 
• 623-03-0 4-Cyanochlorobenzene 
• 3335-29-3 (4-chlorophenyl)(piperidin-1-yl)methanethione 
• 40546-41-6 ethyl-4-chlorobenzimidate hydrochloride 
• 104-88-1 4-chlorobenzaldehyde 
• 37932-45-9 3,6-bis-(4-chloro-phenyl)-[1,2,4,5]tetrazine 
• 4111-54-0 lithium diisopropyl amide 

Downstream Products

• 37932-45-9 3,6-bis-(4-chloro-phenyl)-[1,2,4,5]tetrazine 
• 1331837-31-0 bis(cyclohexylmethyl) 3,6-bis(4-chlorophenyl)-1,2,4,5-tetrazine-1,2-dicarboxylate 

Relevant articles and documents

Synthesis, structure analysis, antitumor evaluation and 3D-QSAR studies of 3,6-disubstituted-dihydro-1,2,4,5-tetrazine derivatives

3,6-Diaryl-dihydro-1,2,4,5-tetrazine derivatives were synthesized and their structures were confirmed by single-crystal X-ray diffraction. Monosubstituted dihydrotetrazines are the 1,4-dihydro structure, but disubstituted dihydrotetrazines are the 1,2-dihydro structure. The results of further research indicated there may be a rearrangement during the synthesis process of disubstituted dihydrotetrazines. Their antitumor activities were evaluated against A-549 and P388 cells in vitro. The results showed several compounds to be endowed with cytotoxicity in the low micromolar range. Two compounds were highly effective against A-549 cell and IC50 values were 0.575 and 2.08 μM, respectively. Three-dimensional quantitative structure-activity relationship (3D-QSAR) studies of comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) were carried out on 37 1,2,4,5-tetrazine derivatives with antitumor activity against A-549 cell. Models with good predictive abilities were generated with the cross validated q2 values for CoMFA and CoMSIA being 0.744 and 0.757, respectively. Conventional r2 values were 0.978 and 0.988, respectively, the predicted R2 values were 0.916 and 0.898, respectively. The results provide the tool for guiding the design and synthesis of novel and more potent tetrazine derivatives.

Synthesis and structure of bis(cyclohexylmethyl) 3,6-bis(4-chlorophenyl)-1, 2,4,5-tetrazine-1,2-dicarboxylate

Bis(cyclohexylmethyl) 3,6-bis(4-chlorophenyl)-1,2,4,5-tetrazine-1,2- dicarboxylate was prepared from cyclohexyl-methyl chloroformate and 3,6-bis(4-chlorophenyl)-1,2(or 1,4)-dihydro-1,2,4,5-tetrazine and its structure was determined by X-ray diffraction. This reaction yields the title compound rather than bis(cyclohexylmethyl) 3,6-bis(4-chlorophenyl)-1,2,4,5-tetrazine-1,4- dicarboxylate. The 2,3-diazabutadiene group in the central six-membered ring of tetrazine is not planar and the tetrazine ring has a twist conformation.

Synthesis, structure analysis, and antitumor activity of 3,6-disubstituted-1,4-dihydro-1,2,4,5-tetrazine derivatives

Fourteen compounds of 3,6-disubstituted-1,4-dihydro-1,2,4,5-tetrazine derivatives were prepared and their structures were confirmed by single-crystal X-ray diffraction and the semi-empirical calculation of PM3 method. This reaction yields the 1,4-dihydro derivatives rather than the 1,2-dihydro derivatives. The central six-membered ring of 1,4-dihydro-1,2,4,5-tetrazine has a chair conformation and therefore is not homoaromatic. Their antitumor activities were evaluated in vitro by SRB method for A-549 and BEL-7402 cells, and MTT method for P-388 and HL-60 cells. The results show that there is one compound which is highly effective against P-388 cells and one compound which is highly effective against HL-60 cells. So it is a kind of compound which possesses potential antitumor activities and is worth to research further.

Diazocinones: Synthesis and conformational analysis

1,2,4,5-Tetrazines (prepared from aryl nitriles) condense with isoxazolylcyclobutanones (prepared from 3-benzenesulfonyl-3-vinylcyclobutanol) in methanolic KOH to give conformationally restricted 6-isoxazol-5-yl-6,7- dihydro-5H-[1,2]diazocin-4-ones. The s

Synthesis and antitumor activity of s-tetrazine derivatives

Fifty-five compounds of s-tetrazine derivative including hexahydro-, 1,6-dihydro, 1,4-dihydro-, 1,2-dihydro- and aromatic s-tetrazine were prepared. Their antitumor activities were evaluated in vitro by MTT method for P-388 cell and SRB method for A-549 cell. The results show that there are 9 compounds which in 10-6 μM have more than 50% inhibition rate to A-549 cancer cell growth, and 7 compounds in 10-6 μM have more than 50% inhibition rate to P-388 cancer cell growth. The IC50 of compound 3q for P-388, Bel-7402, MCF-7 and A-549 are 0.6 μM, 0.6 μM, 0.5 μM and 0. 7 μM, respectively. So s-tetrazine derivative is a kind of compound which possesses potential antitumor activities and is worth to research further.

BADANIA W DZIEDZINIE TIOAMIDOW I ICH POCHODNYCH IX. SYNTEZA POCHODNYCH 1,2,4,5-TETRAZYNY

In reactions of N,N-disubstituted thioamides, derivatives of 4-thiobenzoylmorpholine, 1-thiobenzoylpiperidine and N1,N2-di(α-morpholinobenzylidene)azine, N1,N2-di(α-piperidinobenzylidene)azine also 4-(R-α-phenylaminobenzylidene)morpholinium and 1-(R-α-phenylaminobenzylidene)piperidinium iodides with hydrazine there was obtained a series compounds, derivatives of 1,2,4,5-tetrazine.Structures of obtained compounds have been determined by elemental analysis and on the ground of their UV and IR spectra.

The Role of Lithium Amides as Reducing Agents in a Novel Pathway to 3,6-Diarylpyridazines by Ring Transformations of 3,6-Diaryl-s-tetrazines

3,6-Diaryl-s-tetrazines undergo two competing reactions when treated with lithium amides.The first, direct nucleophilic attack and addition of lithium amide to the tetrazine, appears to be predominant when a less hindered amide is used, and moderate quantities of tetrazine are then regenerated on quenching.The competing reaction, which is seen more clearly with a bulkier amide such as lithium di-isopropylamide, involves reduction of tetrazine to a dihydro derivative with concomitant formation of imine from the amide: this imine is then attacked by further amide and gives rise to a charged intermediate which reacts with more tetrazine to form a pyridazine.