1046-56-6

Usage

Uses

Used in Analytical Chemistry:
3-(2-Pyridyl)-5,6-diphenyl-1,2,4-triazine is used as a chromogenic-extraction reagent for the spectrophotometric determination of iron in acids and acidic solutions. Its ability to react with iron ions allows for the development of a color change that can be measured and correlated to the concentration of iron present in the sample.
Additionally, 3-(2-Pyridyl)-5,6-diphenyl-1,2,4-triazine is used as a precolumn derivatizing reagent in the High-Performance Liquid Chromatography (HPLC) method with UV absorbance detection for the determination of Fe(II). This application takes advantage of PDT's reactivity with Fe(II) to form a derivative that can be separated and detected using HPLC, providing a sensitive and accurate method for Fe(II) analysis.

Indications

PDT with 20% ALA may be used for the treatment of actinic keratoses. The product is marketed as Levulan Kerastick (DUSA Pharmaceuticals, Valhalla, New York). The ALA is applied diffusely over the field with an applicator; the patient returns 1 to 3 hours later and is exposed to an activating light source. Once exposed to the light, ALA produces singlet oxygen, which damages the cell membrane. Sixty-six percent of patients had total clearing of lesions at 8 weeks using blue light exposure for 15 minutes. Patients experience a burning pain but heal with an excellent cosmetic result. Photosensitivity lasts for 24 hours. An optional regimen is to apply ALA only to visible actinic keratoses; however, this method will not treat subclinical lesions. A variety of lasers and light sources can be used to activate the ALA, including blue light, yellow light, and broadband light; however, many details remain to be worked out, such as the optimal incubation times for the ALA when using each of the various light sources.

Purification Methods

Purify it by repeated recrystallisation from EtOH/dimethylformamide. It is a reagent for estimating Fe(II) and Ru(II). [Chriswell & Schilt Anal Chem 46 992 1974, Kamra & Ayers Anal Chem 78 423 1975.]

InChI:InChI=1/C20H14N4/c1-3-9-15(10-4-1)18-19(16-11-5-2-6-12-16)23-24-20(22-18)17-13-7-8-14-21-17/h1-14H

Upstream product

• 1452-63-7 picolinic acid hydrazide 
• 134-81-6 benzil 
• 453556-95-1 6-phenyl-3-(2'-pyridyl)-1,2,4-triazine-4-oxide 
• 100-70-9 2-Cyanopyridine 
• 4930-98-7 pyrid-2-ylhydrazine 
• 1005-02-3 picolinamidrazone 
• 1005-02-3 pyridine-2-carboxamidrazone 
• 65520-11-8 2-cyano-pyridine hydrochloride 
• 74222-83-6 benzamidine hydrochloride dihydrate 
• 73720-51-1 3-Phenyl-6-pyridin-2-yl-[1,2,4,5]tetrazine 
• 618-39-3 benzamidin 

Downstream Products

• 493-77-6 2,4,6-triphenyl-1,3,5-triazine 
• 78386-71-7 2,4-di-phenyl-6-(pyridin-2-yl)-1,3,5-triazine 
• 954099-71-9 [ReCl₃(triphenylphosphineoxide)(5,6-diphenyl-3-(2-pyridyl)-1,2,4-triazine)]*CH₂Cl₂ 
• 1070909-69-1 chloro(2,2':6',2''-terpyridine)(5,6-diphenyl-3-(2-pyridyl)-as-triazine)ruthenium(II) perchlorate 
• 954099-72-0 [ReCl₃(triphenylphosphine)(5,6-diphenyl-3-(2-pyridyl)-1,2,4-triazine)] 
• 1046146-98-8 [(η6-toluene)(5,6-diphenyl-3-(pyridine-2-yl)-1,2,4-triazine)chlororuthenium(II)] hexafluorophosphate 
• 936355-18-9 [(η6-benzene)(5,6-diphenyl-3-(pyridine-2-yl)-1,2,4-triazine)chlororuthenium(II)] hexafluorophosphate 
• 1002728-66-6 [CuCl₂(5,6-diphenyl-3-(2-pyridyl)-1,2,4-triazine)] 
• 1254839-21-8 Cu(5,6-diphenyl-3-(2-pyridyl)-1,2,4-trazine)2(μ-Cl)HgCl3 

Relevant academic research and scientific papers

Broadening the scope of 1,2,4-triazine synthesis by the application of microwave technology

By the application of microwave technology, a general protocol has been developed for the rapid synthesis of diverse 3,5,6-trisubstituted 1,2,4-triazines in excellent yield and purity, including many previously unknown 3-heterocyclic-1,2,4-triazines.

Synthesis, crystal structure, bovine serum albumin binding studies of 1,2,4-triazine based copper(I) complexes

A series of new copper complexes have been synthesized and completely characterized by pivotal analytical techniques. The coordination geometry around copper(I) complex was best described as distorted tetrahedral geometry. The binding of bovine serum albumin with Cu(I) complexes are also been investigated. The Stern–Volmer analysis on quenching data exhibits the presence of the static quenching mechanism. The binding constants were calculated using modified Stern-Volmer, Lineweaver–Burk and Scatchard plots. All the complexes exhibit the binding constants in the order of 104. Thus, these results can contribute to the development of Cu(I) based drugs.

Efficient Preparation of Pyridinyl-1,2,4-Triazines via Telescoped Condensation with Diversely Functionalized 1,2-Dicarbonyls

The development of materials for efficient chemoselective extraction of minor actinides remains at the forefront of research efforts in the area of separation science. Lewis basic complexants derived from nitrogen-donor scaffolds are often employed in this area due to favorable complexation with the transuranic element americium. In the present work an efficient procedure for the preparation of eight useful 3-pyridin-2-yl-1,2,4-triazines (2 novel) is demonstrated via telescoped condensation with the requisite 1,2-dicarbonyl in two-pots without additives, differentially extractive work-up procedures, or recrystallization. Additional efforts in this area have demonstrated the utility of polar aprotic solvents for the preparation of nine functionalized pyridinyl-2,6-bis-1,2,4-triazines (4 novel) directly from the requisite 2,6-pyridine dicarbonitrile in 49–99% yield over four total steps. The streamlined preparation of these important materials and detailed synthetic procedures is reported herein.

Aromatic nucleophilic substitution in 1,2,4-triazine 4-oxides with Grignard reagents

Addition of the Grignard reagents to 1,2,4-triazine 4-oxides followed by aromatization of the intermediate σH-adducts by dehydrogenation or dehydration was used for synthesis of 5-alkyl- or 5-aryl-substituted 1,2,4-triazines and their 4-oxides.

Ferroin reagent

3-(2-pyridyl)-5,6-bis(phenylsulfonic acid)-1,2,4-triazine and certain salts thereof, e.g.--sodium, are provided together with a method for forming such compounds. These compounds are useful as reagents in the spectrophotometric determination of iron in water or other solutions.

DIELS-ALDER REACTIONS WITH INVERSE ELECTRON DEMAND. II. THE REACTION OF BENZAMIDINE WITH ?-DEFICIENT HETEROAROMATIC COMPOUNDS

Benzamidine (I) reacts with several s-tetrazines to give as-triazines in moderate to good yield, together with some s-triazines; separate experiments have shown that these are due to the fact that (I) also undergoes Diels-Alder-reactions with as- and even with s-triazines.

Pharmacologically active substituted 1,2,4-triazines

Substituted 1,2,4-triazines, compositions thereof and methods of using same are described. The compounds of the invention exhibit a wide range of pharmacological activity including anti-inflammatory, analgesic, anti-pyretic, hypotensive and central nervous system effects.