16303-23-4

Usage

Uses

Used in Flame Retardant Applications:
2,4,6-tris(morpholino)-1,3,5-triazine is used as a flame retardant for enhancing the fire safety of materials such as textiles, plastics, and foams. Its high thermal stability and low toxicity make it particularly suitable for indoor environments where safety and health concerns are paramount.
Used in Corrosion Inhibition:
2,4,6-tris(morpholino)-1,3,5-triazine has been studied for its potential as a corrosion inhibitor, indicating its utility in protecting materials from degradation due to environmental factors, thereby extending their service life and improving performance.
Used in Chemical Synthesis:
As a chemical intermediate, 2,4,6-tris(morpholino)-1,3,5-triazine plays a role in organic synthesis, contributing to the creation of new compounds and materials with specific properties for various industrial applications.

InChI:InChI=1/C15H24N6O3/c1-7-22-8-2-19(1)13-16-14(20-3-9-23-10-4-20)18-15(17-13)21-5-11-24-12-6-21/h1-12H2

Upstream product

• 110-91-8 morpholine 
• 108-77-0 1,3,5-trichloro-2,4,6-triazine 
• 7597-22-0 2-chloro-4,6-di-morpholin-4-yl-[1,3,5]triazine 
• 1530-89-8 N-cyanomorpholine 
• 77287-34-4 formamide 
• 5625-90-1 4-(morpholinomethyl)morpholine 
• 109-02-4 4-methyl-morpholine 

Relevant academic research and scientific papers

4,6-Bis- and 2,4,6-tris-(N,N-dialkylamino)-s-triazines: synthesis, NMR spectra and restricted rotations

Syntheses of various symmetrically and non-symmetrically trisubstituted trazines are reported.Dynamic NMR (1H and 13C) experiments demonstrate that 2,4,6-tris(dialkylamino)-s-triazines show correlated rotations of the alkyl groups in the dialkylamino moieties.Unsymmetrical 2-chloro, 2-alkoxy- and 2-aryloxy-4,6-bis(di-n-alkylamino)-s-triazines display two non-equivalent n-alkyl groups, due to the restricted rotation around the Ar-N bonds.

In vitro cytotoxic activities of 2-alkyl-4,6-diheteroalkyl-1,3,5-triazines: New molecules in anticancer research

The cytotoxic activities of new 2-alkyl-4,6-dihetero-(N,O)alkyl-1,3,5- triazines toward selected tumor cell lines have been evaluated, and for the first time, the potential of 2-alkyl-4,6-dialkoxy-1,3,5-triazines has been shown.

Kinetic Studies on the Reaction of Cyanuric Chloride with Amines

The individual steps in the reactions of cyanuric chloride with n-butyl amine in N-methyl pyrrolidone (NMP) and with morpholine in isopropanol (i-PrOH) were followed kinetically.The ratio of the exchange rates of the first, the second and the third chlorine atom was unexpectedly high in both cases.The reactions of n-butylamino dichlorotriazine with several amines were studied kinetically both in NMP and in i-PrOH.Linear free-energy relationships exist both between our values and reaction rates of p-nitro fluorobenzene with the corresponding amines (in DMSO) determined by Suhr.

A practical and easy synthesis of 2,4,6-trisubstituted-s-triazines

Triflic anhydride was found to be efficient for the cyclotrimerization of dialkylcyanamides under mild conditions. The same reaction can be applied to aryl nitriles and thiocyanates.

Synthesis of some 1,3,5-triazine derivatives

Some derivatives of 1,3,5-triazine were prepared with excellent yields by nucleophilic reactions between cyanuric chloride and some nucleophiles under mild conditions.{A figure is presented}.

Synthesis, Spectra, and Theoretical Investigations of 1,3,5-Triazines Compounds as Ultraviolet Rays Absorber Based on Time-Dependent Density Functional Calculations and three-Dimensional Quantitative Structure-Property Relationship

A series of 1,3,5-triazines were synthesized and their UV absorption properties were tested. The computational chemistry methods were used to construct quantitative structure-property relationship (QSPR), which was used to computer aided design of new 1,3,5-triazines ultraviolet rays absorber compounds. The experimental UV absorption data are in good agreement with those predicted data using the Time-dependent density functional theory (TD-DFT) [B3LYP/6–311 + G(d,p)]. A suitable forecasting model (R > 0.8, P 0.0001) was revealed. Predictive three-dimensional quantitative structure-property relationship (3D-QSPR) model was established using multifit molecular alignment rule of Sybyl program, which conclusion is consistent with the TD-DFT calculation. The exceptional photostability mechanism of such ultraviolet rays absorber compounds was studied and confirmed as principally banked upon their ability to undergo excited-state deactivation via an ultrafast excited-state proton transfer (ESIPT). The intramolecular hydrogen bond (IMHB) of 1,3,5-triazines compounds is the basis for the excited state proton transfer, which was explored by IR spectroscopy, UV spectra, structural and energetic aspects of different conformers and frontier molecular orbitals analysis.

Targeting the erythrocytic and liver stages of malaria parasites with s-triazine-based hybrids

A diversity-oriented library of s-triazine-based hybrids was screened for activity against the chloroquine-resistant Plasmodium falciparum W2 strain. The most striking result was sub-micromolar activity against cultured erythrocytic-stage parasites of hybrid molecules containing one or two 8-aminoquinoline moieties. These compounds were not clearly toxic to human cells. The most effective blood-schizontocidal s-triazine derivatives were then screened for activity against the liver stage of malaria parasites. The s-triazine hybrid containing two 8-aminoquinoline moieties and one chlorine atom emerged as the most potent against P. berghei liver-stage infection, active in the low nanomolar region, combined with good metabolic stability in rat liver microsomes. These results indicate that s-triazine-8-aminoquinoline-based hybrids are excellent starting points for lead optimization as dual-stage antimalarials.

The umpolung of substituent effect in nucleophilic aromatic substitution. A new approach to the synthesis of N,N-disubstituted melamines (triazine triskelions) under mild reaction conditions

By the umpolung of substituent effect 1,3,5-triazines substituted with three dialkylamino groups were prepared under mild reaction conditions by treatment of cyanuric chloride with tertiary amines. Quaternary N-triazinylammonium salts were identified as reactive intermediates activating the triazine ring and strongly promoting the persubstitution of all chlorine atoms. The final degradation of intermediate N-triazinylammonium chlorides proceeded at room temperature or in boiling dichloromethane spontaneously within irreversible evolution of appropriate chloroalkane.

Synthesis and antitumor evaluation of a novel series of triaminotriazine derivatives

A series of triaminotriazine derivatives (compounds 5a-f, 6a-x, and 7a-g) was designed, synthesized, and evaluated for their inhibition activities to colorectal cancer (CRC) cell lines (HCT-116 and HT-29). Most of the synthesized compounds demonstrated moderate anti-proliferatory effects on both HCT-116 and HT-29 cell lines at the concentration of 10 μM. The inhibitory activities against HCT-116 and HT-29 cell lines were discussed to develop the structure-activity relationships of this new series. Compounds 6l and 6o exhibited prominent inhibition activities toward HCT-116, with IC50s of 0.76 and 0.92 μM, respectively. The in vivo antitumor studies and pharmacokinetics of compound 6l showed that it might be a promising new hit for further development of antitumor agents.

A convenient method for the preparation of some new derivatives of 1,3,5-s-triazine under solvent free condition

Nucleophilic reactions on cyanuric chloride were carried out under solvent free conditions to give 1,3,5-s-triazine derivatives with excellent yields.