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
• Article Data: 7

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

General Description

3,6-Bis(4-chlorophenoyl)-1,2-dihydro-1,2,4,5-tetrazine is a chemical compound with the molecular formula C16H10Cl2N6. It is a tetrazine derivative that is commonly used in organic synthesis and chemical research. The compound is a yellow crystalline solid that is insoluble in water but soluble in organic solvents. It is known for its high reactivity and is used in the development of new materials, pharmaceuticals, and dyes. Additionally, 3,6-Bis(4-chlorophenoyl)-1,2-dihydro-1,2,4,5-tetrazine is also employed in the production of polymers and as a reagent in chemical reactions. It is important to handle this chemical with caution, as it may be harmful if ingested or inhaled and can cause skin and eye irritation.

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

• 623-03-0 4-Cyanochlorobenzene 
• 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 
• 40546-41-6 ethyl-4-chlorobenzimidate hydrochloride 
• 3335-29-3 (4-chlorophenyl)(piperidin-1-yl)methanethione 
• 37932-51-7 1,4-dichloro-1,4-bis(4-chlorophenyl)-2,3-diazabutadiene 

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, 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.

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.