2125-23-7

Usage

Uses

Used in Food Industry:
2,4,6-tris(2,4-dihydroxyphenyl)-1,3,5-triazine is used as a colorant and additive for enhancing the appearance of processed meats, sauces, confectionery, and alcoholic beverages. Its ability to improve the visual appeal of these products makes it a popular choice in the food industry.
However, it is important to note that 2,4,6-tris(2,4-dihydroxyphenyl)-1,3,5-triazine has been found to have potential carcinogenic properties in animal studies, which has raised concerns about its safety in food products. Consequently, the use of 2,4,6-tris(2,4-dihydroxyphenyl)-1,3,5-triazine in some food items may be regulated by health authorities to ensure consumer safety.

Synthetic route

1,3,5-trichloro-2,4,6-triazine (108-77-0) + recorcinol (108-46-3) → 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7)

Conditions	Yield
With hydrogenchloride; aluminum (III) chloride In water; nitrobenzene at 5 - 95℃;	89.88%
With hydrogenchloride In nitrobenzene at 20 - 100℃; for 5h; Temperature; Inert atmosphere;	81.98%
With Fe-MIL-101 In 5,5-dimethyl-1,3-cyclohexadiene at 80℃; for 12h; Solvent; Temperature;	80%

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 4-[4-chloro-6-(2,4-dihydroxyphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol + 2,4-bis(2,4-dihydroxyphenyl)-6-(2,4-dimethylphenyl)-s-triazine (25023-99-8) + 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine (1668-53-7) + recorcinol (108-46-3) → 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7)

Conditions	Yield
With aluminium trichloride In m-xylene; chlorobenzene

methyl α-chlorohexanoate (14925-60-1) + 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) → 2-(2,4-dihydroxyphenyl)-4,6-bis(2-hydroxy-4-(1-methoxycarbonylpentoxy)phenyl)-1,3,5-triazine (348144-52-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 2h;	93.29%

methyl α-chlorohexanoate (14925-60-1) + 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) → C42H51N3O12

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 3h;	91.75%

ethyl 3-chloropropanoate (623-71-2) + 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) → C36H39N3O12

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 3h;	90.13%

ethyl 2-chloroheptanoate + 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) → C48H63N3O12

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 3h;	89.48%

1-octyl 2-chloropropanoate + 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) → trioctyl 2,2',2''-(((1,3,5-triazine-2,4,6-triyl)tris(3-hydroxybenzene-4,1-diyl))tris(oxy))tripropanoate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 3h;	86.45%

2-chlorohexanoic acid (29671-30-5) + 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) → C45H55N3O14

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 6h;	86%

1-bromo-hexane (111-25-1) + 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) → 2,4,6-tris(2-hydroxy-3-methyl-4-n-hexyloxyphenyl)-1,3,5-triazine

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80 - 100℃; for 1h; Concentration; Inert atmosphere;	84.1%

1-bromo-butane (109-65-9) + 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) → 2,4-bis(2-hydroxy-4-n-butyloxyphenyl)-6-(2,4-di-n-butyloxyphenyl)-s-triazine (208343-47-9)

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide In toluene at 50 - 80℃; for 7h; Temperature; Solvent; Reagent/catalyst; Inert atmosphere;	83.31%

n-Butyl chloride (109-69-3) + 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) → 2,4-bis(2-hydroxy-4-n-butyloxyphenyl)-6-(2,4-di-n-butyloxyphenyl)-s-triazine (208343-47-9)

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide In toluene at 50 - 76℃; for 7h; Solvent; Temperature; Inert atmosphere;	80.13%

1-bromo-butane (109-65-9) + 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) → 2,4,6-tris[4-(n-butoxy)-2-hydroxyphenyl]-1,3,5-triazine

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 80℃; for 12h; Solvent; Temperature; Reagent/catalyst;	72%

para-nitrophenyl triflate (17763-80-3) + 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) → 2,4,6-tris(4-trifluoromethanesulfonate-2-hydroxyphenyl)-1,3,5-triazine

Conditions	Yield
With sodium carbonate at 20℃; for 3h;	70%

ethyl 2-bromoisobutyrate (600-00-0) + 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) → 2,4,6-tris(2-hydroxy-4-[1-ethyloxycarbonyl-1-methylethoxy]phenyl)-1,3,5-triazine (210432-73-8)

Conditions	Yield
With hydrogenchloride; sodium ethanolate In ethanol
With sodium ethanolate In ethanol at 78℃; for 15.5h;

4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) + Ethyl 2-bromopropionate (535-11-5, 41978-69-2) → 2,4,6-tris(2-hydroxy-4-(1-ethoxycarbonylethoxy)phenyl)-1,3,5-triazine

4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) + 2-bromobutyric acid ethyl ester (533-68-6) → 2,4,6-tris(2-hydroxy-4-(1-ethoxycarbonylpropoxy)phenyl)-1,3,5-triazine

Conditions	Yield
With sodium ethanolate In ethanol for 4h; Heating / reflux;

2-chloro-propionic acid methyl ester (17639-93-9) + 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) → 2,4,6-tris(2-hydroxy-4-(1-methoxycarbonylethoxy)phenyl)-1,3,5-triazine (250264-23-4)

4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) + 2-chloro-propanoic acid, ethyl ester (535-13-7) → 2,4,6-tris(2-hydroxy-4-(1-ethoxycarbonylethoxy)phenyl)-1,3,5-triazine

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 14.5h;

2-bromo-2-methylpropionic acid methyl ester (23426-63-3) + 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) → 2,4,6-tris(4-[1-methoxycarbonyl-1-methylethoxy]-2-hydroxyphenyl)-1,3,5-triazine

Conditions	Yield
With hydrogenchloride; sodium methylate In methanol
With sodium methylate In methanol at 78℃; for 18h;

octyl 2-bromopropionates; mixture of + 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) → 2,4,6-tris(4-[1-octyloxycarbonyl-ethoxy]-2-hydroxyphenyl)-1,3,5-triazines; mixture of + 2-(2,4-bis[octyloxycarbonylethoxy]phenyl)-4,6-bis(2-hydroxy-4-(octyloxycarbonylethoxy)phenyl)-1,3,5-triazines; mixture of

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 14.5h;

methyl 2-bromohexanoate (5445-19-2) + 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) → 2-(2,4-dihydroxyphenyl)-4,6-bis(2-hydroxy-4-(1-methoxycarbonylpentoxy)phenyl)-1,3,5-triazine (348144-52-5)

Conditions	Yield
With sodium carbonate In N-methyl-acetamide

potassium tert-butylate (865-47-4) + propargyl bromide (106-96-7) + 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) → 5,5',5"-tris-propargyloxy-2,2',2"-[1,3,5]-triazine-2,4,6-triyl-tris-phenol (212774-94-2)

Conditions	Yield
In 2-methoxy-ethanol

potassium carbonate (584-08-7) + 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) + 2-chloro-propanoic acid, ethyl ester (535-13-7) → 2,4,6-tris(2-hydroxy-4-(1-ethoxycarbonylethoxy)phenyl)-1,3,5-triazine

Conditions	Yield
With magnesium sulfate In N-methyl-acetamide; dichloromethane

dimethyl sulfate (77-78-1) + 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) → 5,5'-dimethoxy-2,2'-[6-(2,4-dimethoxy-phenyl)-[1,3,5]triazine-2,4-diyl]-bis-phenol (103734-29-8)

Conditions	Yield
Stage #1: 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol With potassium carbonate In N,N-dimethyl-formamide at 80℃; Stage #2: dimethyl sulfate In N,N-dimethyl-formamide at 80℃;

dimethyl sulfate (77-78-1) + 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) → C23H19N3O6 + C24H21N3O6 + 5,5'-dimethoxy-2,2'-[6-(2,4-dimethoxy-phenyl)-[1,3,5]triazine-2,4-diyl]-bis-phenol (103734-29-8)

Conditions	Yield
Stage #1: 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h; Stage #2: dimethyl sulfate In N,N-dimethyl-formamide at 80℃; for 7h; Temperature;

dimethyl sulfate (77-78-1) + 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) → C23H19N3O6 + C24H21N3O6

Conditions	Yield
Stage #1: 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol With potassium carbonate In N,N-dimethyl-formamide at 130℃; Stage #2: dimethyl sulfate In N,N-dimethyl-formamide at 130℃; for 3h;

dimethyl sulfate (77-78-1) + 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol (2125-23-7) → C23H19N3O6 + C22H17N3O6

Conditions	Yield
Stage #1: 4-[4,6-di-(2,4-di-hydroxyphenyl)-1,3,5-triazin2-yl]-benzene-1,3-diol With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 4h; Stage #2: dimethyl sulfate In N,N-dimethyl-formamide at 70℃; for 3h;

Upstream product

• 108-77-0 1,3,5-trichloro-2,4,6-triazine 
• 25023-99-8 2,4-bis(2,4-dihydroxyphenyl)-6-(2,4-dimethylphenyl)-s-triazine 
• 1668-53-7 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine 
• 108-46-3 recorcinol 

Downstream Products

• 348144-52-5 2-(2,4-dihydroxyphenyl)-4,6-bis(2-hydroxy-4-(1-methoxycarbonylpentoxy)phenyl)-1,3,5-triazine 
• 212774-94-2 5,5',5-tris-propargyloxy-2,2',2-[1,3,5]-triazine-2,4,6-triyl-tris-phenol 
• 208343-47-9 2,4-bis(2-hydroxy-4-n-butyloxyphenyl)-6-(2,4-di-n-butyloxyphenyl)-s-triazine 
• 3135-19-1 2,4,6-tris[4-(n-butoxy)-2-hydroxyphenyl]-1,3,5-triazine 
• 103734-29-8 5,5'-dimethoxy-2,2'-[6-(2,4-dimethoxy-phenyl)-[1,3,5]triazine-2,4-diyl]-bis-phenol 
• 250264-23-4 2,4,6-tris(2-hydroxy-4-(1-methoxycarbonylethoxy)phenyl)-1,3,5-triazine 
• 210432-73-8 2,4,6-tris(2-hydroxy-4-[1-ethyloxycarbonyl-1-methylethoxy]phenyl)-1,3,5-triazine 

Relevant academic research and scientific papers

A Derivative of s-Triazine Modified Reduced Graphene Oxide with the Function of UV-absorbing

A new s-triazine derivative modified graphene composite, in which 2,4,6-tri(2,4-dihydroxyphenyl)-1,3,5-triazine (TDTA) was attached onto reduced graphene oxide (rGO) via the noncovalent functionalization approach, named TDTA/rGO, was reported. And the TDTA was synthesized via a Friedel-Crafts reaction. FTIR and NMR spectroscopic characterizations were carried out to confirm the synthesis of TDTA. UV-Vis, XPS and TEM revealed that TDTA molecules were successfully loaded onto graphene sheets by π-π stacking, and the composite is found to improve greatly the dispersity of rGO in DMF and to be a good UV-absorber. TDTA/rGO, A new s-triazine derivative modified graphene composite, in which 2,4,6-tri(2,4-dihydroxyphenyl)-1,3,5-triazine (TDTA) was attached onto reduced graphene oxide (rGO) via the noncovalent functionalization approach, was reported. The composite is found to improve greatly the dispersity of rGO in DMF and to be a good UV-absorber.

Method for preparation of 2, 4, 6-tri (2-hydroxy-4-n-hexyloxyaryl)-1, 3, 5-triazines and intermediates thereof

The present invention relates to a method for preparation of 2, 4, 6-tri (2-hydroxy-4-n-hexyloxyaryl)-1, 3, 5-triazines and intermediates thereof. The method comprises the following steps: resorcinolor 2-methyl resorcinol and cyanuric chloride conduct Friedel-Crafts reaction in a nitrobenzene reaction solvent in the presence of a catalyst aluminum trichloride, a reaction solution with 20-37% hydrochloric acid is hydrolyzed after the reaction is finished, a liquid separation catalyst is added into the hydrolyzed system, an intermediate 2, 4, 6-tri (2, 4-dihydroxyaryl)-1, 3, 5-triazine is obtained through separation, and etherification reaction with halohexane is conducted. The method has the advantages of high reaction yield, no generation of process wastewater, reduction of the generationamount of solid wastes, and suitableness for industrialization.

Preparation method of triazines UV absorbent

The invention relates to a preparation method of 2,4-bi(2-hydroxy-4-butylphenyl)-6-(2,4-dibutylphenyl)-1,3,5-triazine. The method comprises the following steps: (10 carrying out a reaction between cyanuric chloride and resorcinol under the effect of a combined immobilized catalyst to generate a component I which is 2,4, 6-tri(2,4-dihydroxyphenyl)-1, 3, 5-triazine; (2) carrying out a reaction of the compound as shown in formula I and butyl halide under the effects of a phase transfer catalyst and an alkaline solution to obtain the target compound. The method has the following advantages: (1) the combined immobilized catalyst is used and the separation technology of reaction materials is simplified, and the separating effect can be realized by simply filtering the solid catalyst, and thus alarge number of aluminum salt containing acidic wastewater can be decreased; (2) the phase transfer catalyst is used for catalyzing the esterifying reaction, and the process is simplified, a severe anhydrous condition is avoided; compared with traditional Williamoson esterifying reaction, the method has the advantage that a large number of compound salt wastes which are hard to separate can be decreased.

Method for preparing triazine-5

The invention discloses a method for preparing triazine-5 from MOFs (Metal-Organic Frameworks) or modified MOFs under a catalysis function. According to the method, a MOFs or modified MOFs catalyst iseconomic and environmental-friendly, stable in structure and convenient to recycle and use. The method for preparing triazine-5, which is disclosed by the invention, has the advantages of being simple to operate, high in product yield and green and environmental-friendly.

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.

Preparation method of 2,4,6-tri(2',4'-dihydroxyphenyl)-1,3,5-triazine

The invention discloses a synthetic method of 2,4,6-tri(2',4'-dihydroxyphenyl)-1,3,5-triazine. The method comprises the following steps: cyanuric chloride and resorcinol are taken as raw materials and react in an aprotic or protic solvent at the reaction temperature of 20-100 DEG C under the action of a metal oxide or supported solid acid catalyst, 2,4,6-tri(2',4'-dihydroxyphenyl)-1,3,5-triazine is generated, a reaction mixture is filtered and separated, and the catalyst can be recycled and reused after washing. The method has simple reaction steps and low cost; the adopted catalyst is simple, easy to obtain and stable in activity, environmental pollution caused by use of a traditional Lewis acid catalyst is avoided, and good catalytic effect is realized.

Synthesis and intramolecular hydrogen bonding networks of 2,4,6-Tri (o-hydroxyaryl)-1,3,5-Triazines

Functionalized, triaryl substituted triazines were synthesized via the Friedel-Crafts arylation reaction. These conjugated triazines possess unique, intramolecular hydrogen bonding motifs, which provide tunable planarity.

Process for making 2-(2,4,-dihydroxyphenyl) or 2-(2,4-dialkoxyphenyl)-4,6-bisaryl-1,3,5-triazines

Provided is a new process for the preparation of compositions containing at least one triazine ultraviolet light absorber.