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
• Article Data: 9

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

General Description

1,3-Benzenediol, 4,4'-[6-(4-methoxyphenyl)-1,3,5-triazine-2,4-diyl]bis- is a chemical compound that is commonly used as a UV filter in sunscreen products. It is also known by its trade name "Bisoctrizole" and is highly effective in protecting the skin from harmful UVA and UVB rays. 1,3-Benzenediol, 4,4'-[6-(4-methoxyphenyl)-1,3,5-triazine-2,4-diyl]bis- works by absorbing and converting the UV radiation into less harmful energy, reducing the risk of skin damage and sunburn. Its unique molecular structure allows it to provide broad-spectrum protection, making it a valuable ingredient in the formulation of sun protection products. Additionally, it is often used in combination with other UV filters to enhance the overall sun protection factor (SPF) of the product.

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

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

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.

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.

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.