493-77-6

Basic information

• Product Name: 2,4,6-TRIPHENYL-S-TRIAZINE
• Synonyms: 2,4,6-Triphenyltriazine;5-triazine,2,4,6-triphenyl-3;Cyaphenine;Kyaphenine;s-Triazine, 2,4,6-triphenyl-;S-Triphenyltriazine;Triphenyl-s-triazine;2,4,6-TRIPHENYL-1,3,5-TRIAZINE
• CAS NO: 493-77-6
• Molecular Formula: C₂₁H₁₅N₃
• Molecular Weight: 309.36
• EINECS: 207-779-8
• Product Categories: Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Triazines;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 493-77-6.mol
• Article Data: 110

Chemical Properties

• Melting Point: 231-236 °C
• Boiling Point: 230°C/0.01mmHg(lit.)
• Flash Point: 245.5 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.1645 (rough estimate)
• Refractive Index: 1.6380 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 1.05±0.10(Predicted)
• CAS DataBase Reference: 2,4,6-TRIPHENYL-S-TRIAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-TRIPHENYL-S-TRIAZINE(493-77-6)
• EPA Substance Registry System: 2,4,6-TRIPHENYL-S-TRIAZINE(493-77-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 493-77-6(Hazardous Substances Data)

Usage

Chemical Properties

white to off-white crystalline powder

Uses

2,4,6-Triphenyl-1,3,5-triazine has been used as a hole-blocking material for electroluminescent devices (ELD).

General Description

Hole blocking capability of 2,4,6-triphenyl-1,3,5-triazine as a non-transporting filler material has been investigated.

InChI:InChI=1S/C21H15N3/c1-4-10-16(11-5-1)19-22-20(17-12-6-2-7-13-17)24-21(23-19)18-14-8-3-9-15-18/h1-15H

Upstream product

• 108-86-1 bromobenzene 
• 108-77-0 1,3,5-trichloro-2,4,6-triazine 
• 591-50-4 iodobenzene 
• 15421-92-8 N-benzylbenzamidine 
• 55-21-0 benzamide 
• 62-53-3 aniline 
• 16776-73-1 N-benzoyl-benzamidine 
• 100-46-9 benzylamine 
• 35401-80-0 1-Methyl-3,6-diphenyl-1,4-dihydro-1,2,4,5-tetrazin 
• 1198-98-7 5-methyl-3-phenyl-1,2,4-oxadiazole 
• 104-87-0 4-methyl-benzaldehyde 
• 100-51-6 benzyl alcohol 
• 90095-57-1 N-(N'-benzoylbenzimidoyl)sulfinylamine 
• 90095-56-0 N,N-dichloro-N'-benzoylbenzamidine 

Downstream Products

• 7664-41-7 ammonia 
• 65-85-0 benzoic acid 
• 618-39-3 benzamidin 
• 211929-01-0 6,8-diphenylbenzo[gh]perimidine 
• 56314-41-1 6⁽⁷⁾-benzoylperimidine 
• 1345690-20-1 2,4,6-triphenyl-1,3,5-triazine-1-oxide 
• 1345690-21-2 2-methyl-2,4,6-triphenyl-1,2-dihydro-1,3,5-triazine-1-oxide 
• 1345690-22-3 2,2,4,6-tetraphenyl-1,2-dihydro-1,3,5-triazine-1-oxide 
• 1345690-28-9 2-methyl-2,4,6-triphenyl-1,2-dihydro-1,3,5-triazinyl-1-oxy 
• 1345690-29-0 2,2,4,6-tetraphenyl-1,2-dihydro-1,3,5-triazinyl-1-oxy 
• 7086-13-7 2,4,6-triphenyl-2,3-dihydro-1,3,5-triazine 
• 30363-03-2 2,4,6-tris(4-bromophenyl)-1,3,5-triazine 
• 14043-38-0 2,4,6-tris(3-nitrophenyl)-1,3,5-triazine 
• 484-47-9 lophine 

Relevant articles and documents

Diverse reactivity of rhodium β-(tetraphenyl)tetraphenyl porphyrin chlorides with benzonitrile: Formation of Rh porphyrin arene and imine complexes

The reaction of rhodium trichloride with β-(tetraphenyl)tetraphenyl porphyrin, H2(tpp)(Ph)4, and β-(tetraphenyl)tetrakismesityl porphyrin, H2(tmp)(Ph)4, in refluxing benzonitrile gave novel rhodium porphyrin chl

Direct Synthesis of a Covalent Triazine-Based Framework from Aromatic Amides

There have been extensive efforts to synthesize crystalline covalent triazine-based frameworks (CTFs) for practical applications and to realize their potential. The phosphorus pentoxide (P2O5)-catalyzed direct condensation of aromatic amide instead of aromatic nitrile to form triazine rings. P2O5-catalyzed condensation was applied on terephthalamide to construct a covalent triazine-based framework (pCTF-1). This approach yielded highly crystalline pCTF-1 with high specific surface area (2034.1 m2 g?1). At low pressure, the pCTF-1 showed high CO2 (21.9 wt % at 273 K) and H2 (1.75 wt % at 77 K) uptake capacities. The direct formation of a triazine-based COF was also confirmed by model reactions, with the P2O5-catalyzed condensation reaction of both benzamide and benzonitrile to form 1,3,5-triphenyl-2,4,6-triazine in high yield.

Butyllithium-induced Cyclotrimerisation Reactions of Organic Nitriles: Solvent Dependency, Crystal and Solution Structures of Lithio Triazine Intermediates and an Unexpected Rearrangement of Dihydrotriazino Anions

Sequential addition of ButCN and PhCN (2 equiv.) to BunLi in the presence of tetrahydrofuran (THF) produces an isolable lithio 1,4-dihydrotriazine tris(THF) solvate, characterised by both NMR spectroscopic and X-ray crystallographic methods, which converts to a 1,2-dihydro arrangement on methanolysis.

Direct synthesis of covalent triazine-based frameworks (CTFs) through aromatic nucleophilic substitution reactions

Despite extensive efforts, only three main strategies have been developed to synthesize covalent triazine-based frameworks (CTFs) thus far. We report herein a totally new synthetic strategy which allows C-C bonds in the CTFs to be formed through aromatic nucleophilic substitution reactions. The as-synthesized CTF-1 and CTF-2 exhibited photocatalytic water splitting activity comparable to the CTFs made using ionothermal or Br?nsted acid-catalyzed polymerization. Interestingly, CTF-2 distinguished itself by its two-photon fluorescence (emission at ～530 nm under irradiation at either 400 nm or 800 nm).

Functionalized fluorenes via dicationic electrophiles

Dicationic fluorenyl cations are shown to react with nitriles to provide amide-functionalized fluorenes. A similar reaction with alcohols gives ether derivatives. The chemistry is initiated by the reactions of N-heterocyclic ketones in a superacidic solution. This leads to cyclizations involving 2-biphenyl groups and formation of the reactive fluorenyl cations.

Synthetic and theoretical MO calculational studies of lithiotriazine intermediates produced during alkyllithium-induced cyclotrimerisation reactions of organic nitriles, and comparison of their structures with that of a methylmagnesiotriazine derivative

Benzonitrile can be readily cyclotrimerised by treatment with a suitable alkyllithium to give a simple triazine or to a solvated lithiodihydrotriazine derivative.Which cyclic product dominates depends mainly on the source of the active Li+ cation (n-butyllithium, t-butyllithium and tetramethylguanidinolithium are considered here), and on the solvent employed.X-ray crystallographic studies on a representative compound show that the lithio species exists as a mononuclear, contact ion pair structure, with the triazine ring in a 1,4-dihydro state.On reaction with theGrignard reagent, MeMgCl, this compound gives a methylmagnesiodihydrotriazine, which has also been crystallographically characterised and found to closely resemble its lithio precursor.Ab initio MO calculations on model systems reveal that the 1,4-dihydrotriazine arrangements is energetically preferred to the 1,2-dihydro alternative irrespective of the counterion (Li+ or H+) present.A theoretical investigation of the methanolysis of the lithio species indicates that the formation of an intermediate MeOH complex, with the alcohol attached to a ring N atom and not to Li+, directs the reaction towards ultimate formation of a 1,2-dihydrotriazine.Keywords: Triazine; Lithium; Magnesium; Ab initio; Crystal structure

One-pot synthesis of new heterocycles: 2,4-disubstituted 6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidines

The reaction of 1-benzosuberone with nitriles in the presence of triflic anhydride affords in good yields 2,4-diaryl substituted 6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidines, a new class of heterocycle.

Solvothermal Reactions in and with Nitriles

Solvothermal reactions and in situ reductions in nitriles yield a variety of new metal complexes and organometallic compounds including ligands of dimers, trimers, and tetramers of the organic solvent upon (oxidative) C-C and/or C-N bond formation and destruction.

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Sustainable and recyclable magnetic nanocatalyst of 1,10-phenanthroline Pd(0) complex in green synthesis of biaryls and tetrazoles using arylboronic acids as versatile substrates

A magnetic nanocatalyst was purveyed as a heterogeneous recoverable palladium-based catalyst anchored on green, sustainable and phosphine free support. Resulted Fe3O4@SiO2-Phen-Pd(0) nanocatalyst bearing powerful phenanthroline ligand was thoroughly characterized by physicochemical approaches like UV–vis, FT-IR, EDX, XRD, TGA, ICP, VSM, DLS, FESEM, and TEM analyses. After finding trustable data, the obtained magnetic catalyst was considered to be applied in the Suzuki-Miyaura type C-C couplings and getting corresponding tetrazoles using arylboronic acid derivatives as alternate precursors of aromatic halides and stupendous data were observed.

Iron-Catalyzed Alkyne-Based Multicomponent Synthesis of Pyrimidines under Air

An iron-catalyzed sustainable, economically affordable, and eco-friendly synthetic protocol for the construction of various trisubstituted pyrimidines is described. A wide range of trisubstituted pyrimidines were prepared using a well-defined, easy to prepare, bench-stable, and phosphine-free iron catalyst featuring a redox-noninnocent tridentate arylazo pincer under comparatively mild aerobic conditions via dehydrogenative functionalization of alcohols with alkynes and amidines.

Multifunctional aggregation-induced emission material and preparation method thereof

The invention belongs to the technical field of photoelectric display devices, and particularly relates to a multifunctional aggregation-induced emission material and a preparation method thereof. The invention provides a multifunctional aggregation-induced emission material. The structure of the multifunctional aggregation-induced emission material is shown as a formula (I). The invention also provides a preparation method of the multifunctional aggregation-induced emission material, and the preparation method comprises the step of carrying out substitution reaction on 2, 4, 6-tri (4-bromophenyl)-1, 3, 5-triazine and the compound as shown in the formula (II) to prepare the compound as shown in the formula (I). The invention solves the technical problems that the efficiency of the existing TADF micromolecule red light emitting material and the electroluminescent device thereof is not high, and the aggregation quenching luminescence effect is easy to generate.