2547-66-2

Basic information

• Product Name: 1,3,5-TRIBENZYLHEXAHYDRO-1,3,5-TRIAZINE
• Synonyms: 1,3,5-Triazine, hexahydro-1,3,5-tris(phenylmethyl)-;1,3,5-TRIBENZYLHEXAHYDRO-1,3,5-TRIAZINE 98+%;Hexahydro-1,3,5-tribenzyl-1,3,5-triazine;Hexahydro-1,3,5-tris(phenylmethyl)-1,3,5-triazine;1,3,5-Tribenzyl-1,3,5-triazinane;1,3,5-Tribenzylhexahydro-1,3,5-triazine 98%;1,3,5-TRIBENZYLHEXAHYDRO-1,3,5-TRIAZINE;1,3,5-TRIBENZYLHEXAHYDRO-S-TRIAZINE
• CAS NO: 2547-66-2
• Molecular Formula: C₂₄H₂₇N₃
• Molecular Weight: 357.49
• EINECS: 219-831-7
• Product Categories: Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Triazines;Heterocyclic Building Blocks
• Mol File: 2547-66-2.mol

Chemical Properties

• Melting Point: 49-51 °C(lit.)
• Boiling Point: 100 °C0.005 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 113
• Vapor Pressure: 7.94E-09mmHg at 25°C
• Refractive Index: 1.6270 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 5.46±0.20(Predicted)
• CAS DataBase Reference: 1,3,5-TRIBENZYLHEXAHYDRO-1,3,5-TRIAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-TRIBENZYLHEXAHYDRO-1,3,5-TRIAZINE(2547-66-2)
• EPA Substance Registry System: 1,3,5-TRIBENZYLHEXAHYDRO-1,3,5-TRIAZINE(2547-66-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 2547-66-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
1,3,5-TRIBENZYLHEXAHYDRO-1,3,5-TRIAZINE is used as a reagent in the synthesis of phosphinic acid-based N-Acetylated alpha-linked acidic dipeptidase (NAALADase) inhibitors. These inhibitors may potentially be used for the treatment of both neurodegenerative disorders and peripheral neuropathies, offering therapeutic benefits in managing these conditions.
Used in Catalyst Assembling Process:
1,3,5-TRIBENZYLHEXAHYDRO-1,3,5-TRIAZINE serves as a ligand in the synthesis of alkyl β-aminocarboxylates via trifluoromethanesulfonic acid catalyzed reaction with ketene silyl acetals. This application is crucial in the development of new catalysts and their optimization for various chemical reactions.
Used in Heterogeneous Cr-based Single-site Ethylene Trimerization Catalyst:
1,3,5-TRIBENZYLHEXAHYDRO-1,3,5-TRIAZINE is used as a ligand to study the assembling process of a heterogeneous Cr-based single-site ethylene trimerization catalyst by X-ray absorption spectroscopy. This application aids in understanding the structure and function of these catalysts, which are essential for the production of valuable chemicals and materials.
Used in Conversion of Phillips Cr/SiO2 Polymerisation Catalyst:
1,3,5-TRIBENZYLHEXAHYDRO-1,3,5-TRIAZINE is used as a ligand during the conversion of Phillips Cr/SiO2 polymerisation catalyst to an ethylene trimerisation catalyst after assembling new active sites on the silica surface. This process is vital for the development of more efficient and selective catalysts for industrial applications.

Synthesis

To a round-bottomed flask (125 mL) equipped with a reflux condenser was added theappropriate amine (0.05 mmol), toluene (40 mL) and formaldehyde (37%, 4.1 mL).The solution was brought to reflux using an external oil bath and kept stirring for 30min. Then, the toluene was evaporated under reduced pressure, and the residue wasdissolved in ethyl acetate and washed with a saturated aqueous solution of sodiumchloride. After evaporation of the solvent under reduced pressure in a rotaryevaporator, the residue was purified by silica gel column chromatography usinghexane/ethyl acetate 9:1 as the eluent.

InChI:InChI=1/C24H27N3/c1-4-10-22(11-5-1)16-25-19-26(17-23-12-6-2-7-13-23)21-27(20-25)18-24-14-8-3-9-15-24/h1-15H,16-21H2/p+3

Upstream product

• 123-91-1 1,4-dioxane 
• 14173-62-7 1,7-diacetoxy-2,4,6-trinitro-2,4,6-triazaheptane 
• 100-46-9 benzylamine 
• 98593-84-1 N-benzylaminomethanesulfonic acid 
• 50-00-0 formaldehyd 
• 75-09-2 dichloromethane 
• 16574-19-9 5-allyl-1,3-dioxa-5-azacyclohexane 
• 14133-70-1 1-acetoxy-2,4,6-trinitro-2,4,6-triazaheptane 
• 88891-55-8 5-(2-hydroxyethyl)hexahydro-1,3,5-dithiazine 
• 633336-01-3 (+/-)-2-(1,3,5-dithiazinan-5-yl)-1-methylethanol 
• 100-44-7 benzyl chloride 
• 5400-93-1 1-benzyl-3,5,7-triaza-1-azoniatricyclo<3,3,1,1^3,7>decane chloride 

Downstream Products

• 5694-20-2 N-benzylidenemethylamine 
• 72531-49-8 N-Acetylthiomethyl-N-benzyl-acetylthioacetamid 
• 50917-70-9 (benzylaminomethyl)phosphonic acid diethyl ester 
• 73698-53-0 2,9-dibenzyl-1,2,3,8,9,10-hexahydro-benzo[2,1-e;3,4-e']bis[1,3]oxazine 
• 500357-91-5 3,8-dibenzyl-2,3,4,7,8,9-hexahydro-benzo[1,2-e;4,5-e']bis[1,3]oxazine 
• 6342-10-5 2-benzyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine 
• 107398-53-8 5-cyano-5-ethoxycarbonyl-1,3-dimethyl-hexahydropyrimidine 
• 107398-69-6 1,5-dicyano-3,7-dimethyl-diazabicyclo<3,3,1>nona-2,6-dione 
• 107398-67-4 1,5-dicyano-3,7-diethyl-diazabicyclo<3,3,1>nona-2,6-dione 
• 107398-68-5 3,7-dibenzyl-1,5-dicyano-3,7-diazabicyclo<3,3,1>nona-2,6-dione 
• 107398-54-9 5,5-diethoxycarbonyl-1,3-dimethyl-hexahydropyrimidine 
• 107398-55-0 5,5-diethoxycarbonyl-1,3-diethyl-hexahydropyrimidine 
• 107398-58-3 1,5-diethoxycarbonyl-3,7-dimethyl-3,7-diazabicyclo<3,3,1>nona-2,6-dione 
• 107398-60-7 1,5-diethoxycarbonyl-3,7-diethyl-3,7-diazabicyclo<3,3,1>nona-2,6-dione 

Relevant articles and documents

Structural and Thermodynamics Studies on Polyaminophosphonate Ligands for Uranyl Decorporation

The development of actinide decorporation agents with high complexation affinity, high tissue specificity, and low biological toxicity is of vital importance for the sustained and healthy development of nuclear energy. After accidental actinide intake, sequestration by chelation therapy to reduce acute damage is considered as the most effective method. In this work, a series of bis- and tetra-phosphonated pyridine ligands have been designed, synthesized, and characterized for uranyl (UO22+) decorporation. Owing to the absorption of the ligand and the luminescence of the uranyl ion, UV-vis spectroscopy and time-resolved laser-induced fluorescence spectroscopy (TRLFS) were used to probe in situ complexation and structure variation of the complexes formed by the ligands with uranyl. Density functional theory (DFT) calculations and X-ray absorption fine structure (XAFS) spectroscopy on uranyl-ligand complexes revealed the coordination geometry around the uranyl center at pH 3 and 7.4. High affinity constants (log K ～17) toward the uranyl ion were determined by displacement titration. A preliminary in vitro chelation study proves that bis-phosphonated pyridine ligands can remove uranium from calmodulin (CaM) at a low dose and in the short term, which supports further uranyl decorporation applications of these ligands.

Synthesis of highly functional imidazole derivatives via assembly of 2-unsubstituted imidazole N-oxides with CH-acids and arylglyoxals

A novel and convenient method for the synthesis of a wide range of polyfunctional imidazole derivatives based on the three-component condensation of imidazole N-oxides with CH-acids and arylglyoxals has been developed. This reaction proceeds smoothly in moderate-to-good yields with a wide range of starting materials.

Synthesis and Cytotoxic Activity of Hexahydro-1,3,5-triazine Derivatives through Ring Condensation

As a part of a research program for pharmacologically interacting sym-triazine derivatives with hexahydrotriazine ring, novel hexahydrotriazine derivatives (1?13) were successfully synthesized. The synthesis of hexahydrotriazines was carried out from the assembly of three molecules of various amines and three molecules of formaldehyde by “1 + 1 + 1 + 1 + 1 + 1” cycloaddition. The synthesis mechanism is probably passes through imines, which trimerizes to give the hexahydrotriazine ring. All synthesized hexahydrotriazines (1–13) were screened for their cytotoxic activity by cancer cells. As a result, compound 1–9 reduced the viability of T98G cells in a concentration-dependent manner. At a concentration of 100 μM, compound 9 exhibited the greatest cytotoxicity at 94.6%. The reason is that compound 9 is C5H5N that has a resonance hybrid structure and exhibits aromaticity. It is considered to be active because it has a structure that is a raw material for pyridine derivatives as mainly medicines and pesticides.

Synthesis of α-Amino Tertiary Alkylperoxides by Lewis Acid-Catalyzed Peroxidation of 1,3,5-Triazines

α-Substituted peroxides have been found in natural products and are widely used as anti-malarial agents. Zn(OTf)2-catalyzed peroxidation of 1,3,5-triazines has been developed, accessing diversely substituted α-amino tertiary alkylperoxides with high efficiency. Mechanistic investigations and useful synthetic application of the products have also been presented.

Facile Access to 3-Unsubstituted Tetrahydroisoquinolonic Acids via the Castagnoli-Cushman Reaction

Hitherto undescribed 3-unsubstituted tetrahydroisoquinolonic acids (isolated as their respective methyl esters) were accessed for the first time by the uncatalyzed, thermally promoted Castagnoli-Cushman reaction (CCR) of homophthalic anhydride (HPA) and a series of 1,3,5-triazinanes. The moderate yields observed in some cases are most likely associated with a persistent impurity also formed in these reactions. The new scaffold is expected to find novel medicinal utility (compared to the traditional CCR adducts) because it lacks a substituent at the 3-position.

Gold-Catalyzed Tandem Dual Heterocyclization of Enynones with 1,3,5-Triazines: Bicyclic Furan Synthesis and Mechanistic Insights

A general and unprecedented gold-catalyzed tandem dual heterocyclization reaction of enynones with 1,3,5-triazines has been developed, which provides bicyclic fused furans in high to excellent yields under mild reaction conditions. In addition, mechanistic studies indicate that the reaction goes through a stepwise [3+2+2]-cycloaddition of furanyl gold intermediate, which is generated from gold-catalyzed cyclization of enynone, with two molecules of formaldimines derived in situ from 1,3,5-triazine, instead of formal [4+3]-cycloaddition.

A new and efficient procedure for the synthesis of hexahydropyrimidine-fused 1,4-naphthoquinones

A new and efficient method for the synthesis of hexahydropyrimidine-fused 1,4-naphthoquinones in one step with high yields from the reaction of lawsone with 1,3,5-triazinanes was developed.

Diamino- and mixed amino-amido-N-heterocyclic carbenes based on triazine backbones

The synthesis of novel hexahydrotriazine-based NHCs from easily available starting materials is described. Tribenzyltriazacyclohexane 1 is converted stepwise to the six-membered diamino carbene 3 with a saturated ring structure. Analogously, the cyclic mixed amino-amido carbene 12 is obtained starting from a cyclic urea derivative. Both carbenes were characterized by trapping reactions with sulfur and selenium as well by the preparation of metal complexes of the type (COD)MX-NHC (M = Rh, Ir; COD = 1,5-cyclooctadiene), which were converted to the respective dicarbonyl complexes (CO)2MX-NHC. IR spectra of the carbonyl derivatives allowed the Tolman electronic parameter to be determined for carbenes 3 (2052 cm-1) and 12 (2058 cm-1) and revealed a shift of 6 cm-1 due to the presence of one amide function. X-ray structure determinations are reported for an amidinium species, a carbene sulfide, and the (COD)RhBr complex of the amino-amido carbene 12.

Method of synthesis of phosphinic acids based on hypophosphites: VIII.1 synthesis of α-aminoalkylphenethylphosphinic acids

Development of methodology of double Arbuzov rearrangement based on hypophosphites allows a one-pot formation of two unsymmetrical phosphorus-carbon bonds by the Michael-Pudovik type reaction of stepwise addition of the intermediately forming silyl esters of trivalent phosphorus to different unsaturated compounds. A procedure was developed of the synthesis of α-aminoalkylphenethylphosphinic acids. Bis-(trimethylsilyl) phenethylphosphonite formed as a result of the addition of bis(trimethylsilyl) hypophosphite to styrene in situ was added without isolation from the reaction mixture to Schiff bases obtained preliminary from benzylamine or diphenylmethylamine and various aldehydes. The subsequent removal of N-protecting groups by hydrogenation or acidic hydrolysis gave a number of new α-aminoalkylphenethylphosphinic acids.

COMPOUNDS AND METHODS FOR INHIBITING NHE-MEDIATED ANTIPORT IN THE TREATMENT OF DISORDERS ASSOCIATED WITH FLUID RETENTION OR SALT OVERLOAD AND GASTROINTESTINAL TRACT DISORDERS

The present disclosure is directed to corn- pounds and methods for the treatment of disorders associated with fluid retention or salt overload, such as heart failure (in particular, congestive heart failure), chronic kidney disease, end-stage renal disease, liver disease, and peroxisome proliferator-activated receptor (PPAR) gamma agonist-induced fluid retention. The present disclosure is also directed to compounds and methods for the treatment of hypertension. The present disclosure is also directed to compounds and methods for the treatment of gastrointestinal tract disorders, including the treatment or reduction of pain associated with gastrointestinal tract disorders. The methods generally comprise administering to a mammal in need thereof a pharmaceutically effective amount of a compound, or a pharmaceutical composition comprising such a compound, that is designed to be substantially active in the gastrointestinal (GI) tract to inhibit NHE-mediated antiport of sodium ions and hydrogen ions therein. More particularly, the method comprises administering to a mammal in need thereof a pharmaceutically effective amount of a compound, or a pharmaceutical composition comprising such a compound, that inhibits NHE-3, -2 and/ or -8 mediated antiport of sodium and/or hydrogen ions in the GI tract and is designed to be substantially impermeable to the layer of epithelial cells, or more specifically the epithelium of the GI tract. As a result of the compound being substantially impermeable, it is not absorbed and is thus essentially systemically non-bioavailable, so as to limit the exposure of other internal organs (e.g., liver, heart, brain, etc.) thereto. The present disclosure is still further directed to a method wherein a mammal is administered such a compound with a fluid-absorbing polymer, such that the combination acts as described above and further provides the ability to sequester fluid and/or salt present in the GI tract