1440-00-2

Basic information

• Product Name: 1,3-Benzenediol, 4,4'-[6-(4-methoxyphenyl)-1,3,5-triazine-2,4-diyl]bis-
• Synonyms: 1,3-Benzenediol, 4,4'-[6-(4-methoxyphenyl)-1,3,5-triazine-2,4-diyl]bis- ;4,4'-[6-(4-methoxy-phenyl)-[1,3,5]triazine-2,4-diyl]-bis-benzene-1,3-diol
• CAS NO: 1440-00-2
• Molecular Formula: C₂₂H₁₇N₃O₅
• Molecular Weight: 403.38748
• EINECS: 444-500-0
• Mol File: 1440-00-2.mol

Chemical Properties

• Melting Point: >360 °C
• Boiling Point: 755.6±62.0 °C(Predicted)
• Appearance: /
• Density: 1.427±0.06 g/cm3(Predicted)
• PKA: 8.21±0.40(Predicted)
• CAS DataBase Reference: 1,3-Benzenediol, 4,4'-[6-(4-methoxyphenyl)-1,3,5-triazine-2,4-diyl]bis-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Benzenediol, 4,4'-[6-(4-methoxyphenyl)-1,3,5-triazine-2,4-diyl]bis-(1440-00-2)
• EPA Substance Registry System: 1,3-Benzenediol, 4,4'-[6-(4-methoxyphenyl)-1,3,5-triazine-2,4-diyl]bis-(1440-00-2)

Safety Data

• Hazardous Substances Data: 1440-00-2(Hazardous Substances Data)

Usage

Uses

Used in Sun Protection Products:
1,3-Benzenediol, 4,4'-[6-(4-methoxyphenyl)-1,3,5-triazine-2,4-diyl]bisis used as a UV filter for its ability to protect the skin from harmful UVA and UVB rays. It is particularly effective in sunscreen products due to its broad-spectrum protection, which helps reduce the risk of skin damage and sunburn.
Used in Combination with Other UV Filters:
In the Cosmetics Industry, 1,3-Benzenediol, 4,4'-[6-(4-methoxyphenyl)-1,3,5-triazine-2,4-diyl]bisis used as a synergistic component with other UV filters to enhance the overall sun protection factor (SPF) of the product. This combination provides a more comprehensive defense against the harmful effects of ultraviolet radiation, ensuring better protection for the skin.

Synthetic route

2,4-dichloro-6-(4-methoxy-phenyl)-[1,3,5]triazine (90723-86-7) + recorcinol (108-46-3) → 4-[4-(2,4-dihydroxyphenyl)-6-(4-methoxyphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol (1440-00-2)

Conditions	Yield
With aluminum (III) chloride; 1-methyl-3-propyl-1H-imidazolium chloride at 75℃; for 8h; Reagent/catalyst; Temperature;	96.1%
With aluminum (III) chloride; silica gel In sulfolane at 60 - 80℃; for 10h; Solvent; Temperature; Reagent/catalyst;	86%
Stage #1: 2,4-dichloro-6-(4-methoxy-phenyl)-[1,3,5]triazine With aluminum (III) chloride In chlorobenzene at 25℃; for 0.5h; Inert atmosphere; Stage #2: recorcinol at 85℃; for 5h;	84%

2,4-dichloro-6-(4-methoxy-phenyl)-[1,3,5]triazine (90723-86-7) + recorcinol (108-46-3) → tinosorb S (187393-00-6) + 4-[4-(2,4-dihydroxyphenyl)-6-(4-methoxyphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol (1440-00-2)

Conditions	Yield
aluminium chloride In sulfolane; methanol; 5,5-dimethyl-1,3-cyclohexadiene

4-methoxyphenyl magnesium bromide (13139-86-1) → 4-[4-(2,4-dihydroxyphenyl)-6-(4-methoxyphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol (1440-00-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 10 h / 0 - 45 °C / Inert atmosphere 2.1: aluminum (III) chloride / chlorobenzene / 0.5 h / 25 °C / Inert atmosphere 2.2: 5 h / 85 °C View Scheme

1,3,5-trichloro-2,4,6-triazine (108-77-0) + methoxybenzene (100-66-3) + recorcinol (108-46-3) → 4-[4-(2,4-dihydroxyphenyl)-6-(4-methoxyphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol (1440-00-2)

Conditions	Yield
Stage #1: 1,3,5-trichloro-2,4,6-triazine; methoxybenzene With aluminum (III) chloride In sulfolane at 50 - 60℃; for 2h; Stage #2: recorcinol In sulfolane at 40 - 50℃; for 4h; Solvent;	142 g
Stage #1: 1,3,5-trichloro-2,4,6-triazine; methoxybenzene With aluminum (III) chloride In sulfolane at 50 - 60℃; for 2h; Stage #2: recorcinol In sulfolane at 40 - 50℃; for 4h;	320 g
Stage #1: 1,3,5-trichloro-2,4,6-triazine; recorcinol With aluminum (III) chloride In sulfolane at 50 - 60℃; for 2h; Stage #2: methoxybenzene In sulfolane at 40 - 50℃; for 4h;	318 g

methoxybenzene (100-66-3) → 4-[4-(2,4-dihydroxyphenyl)-6-(4-methoxyphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol (1440-00-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / sulfolane / 40 - 60 °C 2: aluminum (III) chloride / sulfolane / 5 h / 40 - 50 °C View Scheme

glycidyl isopropyl ether (4016-14-2) + ethyltriphenylphosphonium bromide (1530-32-1) + 4-[4-(2,4-dihydroxyphenyl)-6-(4-methoxyphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol (1440-00-2) → 2,4-bis{[4-(3-(2-propyloxy)-2-hydroxypropyloxy)-2-hydroxyphenyl]}-6-(4-methoxyphenyl)-1,3,5-triazine (191419-26-8)

Conditions	Yield
In N-methyl-acetamide; 5,5-dimethyl-1,3-cyclohexadiene; acetone; toluene

4-[4-(2,4-dihydroxyphenyl)-6-(4-methoxyphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol (1440-00-2) → 2,4-bis-[{(4-(3-sulfonato)-2-hydroxypropyloxy)-2-hydroxy}phenyl]-6-(4-methoxyphenyl)-1,3,5-triazine sodium salt

Conditions	Yield
With sodium hydroxide In 2-methoxy-ethanol; acetone

3-(chloromethyl)heptane (123-04-6) + 4-[4-(2,4-dihydroxyphenyl)-6-(4-methoxyphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol (1440-00-2) → tinosorb S (187393-00-6)

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 100 - 143℃; for 7h; pH=7; Reagent/catalyst; Temperature;

2-ethylhexyl bromide (18908-66-2) + 4-[4-(2,4-dihydroxyphenyl)-6-(4-methoxyphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol (1440-00-2) → tinosorb S (187393-00-6)

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 125℃;
With sodium carbonate In N,N-dimethyl-formamide at 125℃;	160 g

3-bromooctane (999-64-4) + 4-[4-(2,4-dihydroxyphenyl)-6-(4-methoxyphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol (1440-00-2) → 2,4-bis((4-(ethyl-hexyloxy)-2-hydroxy)-phenyl)-6-(4-methoxyphenyl)-1,3,5-triazine

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 70℃;

Methyl 2-bromopropionate (5445-17-0) + 4-[4-(2,4-dihydroxyphenyl)-6-(4-methoxyphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol (1440-00-2) → methyl 2-[3-hydroxy-4-[4-[2-hydroxy-4-(2-methoxy-1-methyl-2-oxoethoxy)phenyl]-6-(4-methoxyphenyl)-1,3,5-triazin-2-yl]phenoxy]propanoate

Conditions	Yield
With sodium carbonate In 5,5-dimethyl-1,3-cyclohexadiene; N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere;	103.3 g

Upstream product

• 90723-86-7 2,4-dichloro-6-(4-methoxy-phenyl)-[1,3,5]triazine 
• 108-46-3 recorcinol 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 108-77-0 1,3,5-trichloro-2,4,6-triazine 
• 100-66-3 methoxybenzene 

Downstream Products

• 191419-26-8 2,4-bis{[4-(3-(2-propyloxy)-2-hydroxypropyloxy)-2-hydroxyphenyl]}-6-(4-methoxyphenyl)-1,3,5-triazine 
• 187393-00-6 tinosorb S 

Relevant articles and documents

Manufacturing method of triazine-based compound and derivative thereof

The present invention relates to a triazine-based compound and a process for producing the same. The triazine compound according to an embodiment of the present invention may be prepared by reacting cyanuric acid (Cyanuric Chloride), anisole (anisole) and resorcinol (Resorcinol) to produce a triazine-based compound represented by Formula 1. Chemical Formula 1.

Polymerizable UV absorbers for the UV stabilization of polyesters. I. Design, synthesis and polymerization of a library of UV absorbing monomers

UV stabilizers, such as Tinuvin 1577, are organic additives that are used in the polymer industry to suppress polymer photodegradation, however leaching of the stabilizers from polymers is a significant practical issue which limits the effectiveness of the stabilizers and restricts polymer lifetimes. Novel, polymerizable UV stabilizers were synthesised and copolymerized with bis(2-hydroxyethyl) isophthalate to yield poly(ethylene isophthalate) copolymers where the UV stabilizers are bound covalently into the polymer chains. This strategy prevents leaching of stabilizers from polymers over time, and is expected to lead to enhanced UV protection of polymers compared to the admixing of polymers with UV stabilizers of low molar mass.

A PROCESS FOR THE PREPARATION OF UV ABSORBERS

The presently claimed invention relates to a novel, highly efficient and general process for the preparation of UV absorbers.

Manufacturing method of triazine-based compound and derivative thereof

The present invention relates to a triazine-based compound, and a method for manufacturing derivatives thereof. The method for manufacturing the triazine-based compound according to an embodiment of the present invention can manufacture the triazine-based compound represented by chemical formula 1 by conducting a reaction of cyanuric chloride, anisole, and resorcinol. The method for manufacturing the triazine-based compound according to an embodiment of the present invention can simplify a reaction step.COPYRIGHT KIPO 2020

An ultraviolet absorbent the day executes S intermediate preparation method

The invention relates to an ultraviolet absorbent the day executes S intermediate preparation method, in particular to a 2, 4 - double-(2, 4 - dihydroxy-phenyl) - 6 - (methoxyphenyl) - 1, 3, 5 - triazine. The invention in step (1) in the specific catalyst, direct catalytic cyanuric chloride and anisole for carrying out the alkylation reaction, to obtain intermediate 2, 4 - dichloro - 6 - (methoxyphenyl) - 1, 3, 5 - triazine solution, then put in the resorcinol, sulfolane, catalyst, the reaction is carried out, the filter, the filtrate is hydrolyzed, separating solid, filtered and the solid water washing, drying, to obtain 2, 4 - double-(2, 4 - dihydroxy-phenyl) - 6 - (methoxyphenyl) - 1, 3, 5 - triazine. The invention atom economy high, low material cost, the production low safety risk and less environmental pollution.

Preparation method for 2,4-bi(2,4-dihydroxy phenyl)-6-(4-methoxy phenyl)-s-triazine

The invention discloses a preparation method for 2,4-bi(2,4-dihydroxy phenyl)-6-(4-methoxy phenyl)-s-triazine. According to the method, 2,4-dichloro-6-(4-methoxy phenyl)-s-triazine and resorcinol aretaken as reaction raw materials and an aluminum chlorate ionic liquid is taken as a reaction solvent and a catalyst. An extraction agent is adopted for extracting the product from an ionic liquid catalyst, so that the product can be separated from the catalyst. According to the invention, the aluminum chlorate ionic liquid can be reused, the pressure of three-waste treatment caused by the traditional aluminum trichloride catalyst can be avoided and the preparation method meets the green and environment-friendly requirements.

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.

PROCESS FOR THE PREPARATION OF TRIAZINES

The invention relates to an improved process for the manufacture of bis-resorcinyl triazines of formula (I) wherein R1 is a C1C18alkyl group or C2-C18alkenyl group as well as the respective alkyl substituted bis-resorcinyl derivatives of formula (II) wherein R1 is a C1-C18alkyl group or C2-C18alkenyl group and R2 and R3 are independently of each other a C1-C18alkyl group or a C2-C18alkenyl group.

Bis(resorcinyl)triazines useful as sunscreens in cosmetic preparations

There are described bis(resorcinyl)triazines of the formula STR1 The compounds according to the invention are particularly suitable as sunscreens in cosmetic, pharmaceutical and veterinary medicinal preparations.