187393-00-6

Basic information

• Product Name: BIS-ETHYLHEXYLOXYPHENOL METHOXYPHENYL TRIAZINE
• Synonyms: 2,2′-[6-(4-Methoxyphenyl)- 1,3,5-triazine-2,4-diyl] bis{5-[(2-ethylhexyl)oxy]phenol};2,4-Bis[4-(2-ethylhexyloxy)-2-hydroxyphenyl]-6-(4-methoxyphenyl)-1,3,5-triazine;CGF 1607;FAT 70'884;Tinosorb S Aqua;(6Z)-3-(2-Ethylhexoxy)-6-[(4Z)-4-[4-(2-ethylhexoxy)-6-oxo-1-cyclohexa-2,4-dienylidene]-6-(4-methoxyphenyl)-1H-1,3,5-triazin-2-ylidene]cyclohexa-2,4-dien-1-one;BIS-ETHYLHEXYLOXYPHENOL METHOXYPHENYL TRIAZINE;Phenol, 2,2-6-(4-methoxyphenyl)-1,3,5-triazine-2,4-diylbis5-(2-ethylhexyl)oxy-
• CAS NO: 187393-00-6
• Molecular Formula: C₃₈H₄₉N₃O₅
• Molecular Weight: 627.81276
• Mol File: 187393-00-6.mol

Chemical Properties

• Melting Point: 83-85°; mp 80° (Mongiat)
• Boiling Point: 781.977 °C at 760 mmHg
• Flash Point: 426.724 °C
• Appearance: /
• Density: 1.11 g/cm³
• Vapor Pressure: 1.37E-13mmHg at 25°C
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 8.08±0.40(Predicted)
• BRN: 11322254
• CAS DataBase Reference: BIS-ETHYLHEXYLOXYPHENOL METHOXYPHENYL TRIAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS-ETHYLHEXYLOXYPHENOL METHOXYPHENYL TRIAZINE(187393-00-6)
• EPA Substance Registry System: BIS-ETHYLHEXYLOXYPHENOL METHOXYPHENYL TRIAZINE(187393-00-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 187393-00-6(Hazardous Substances Data)

Usage

Uses

Used in Sunscreen Products:
BIS-ETHYLHEXYLOXYPHENOL METHOXYPHENYL TRIAZINE is used as a broad-spectrum UV absorber for protecting the skin from harmful UVA and UVB rays. Its high fat solubility and photostability contribute to its effectiveness in sunscreen formulations, providing reliable and long-lasting protection against sun damage.
Used in Cosmetics Industry:
BIS-ETHYLHEXYLOXYPHENOL METHOXYPHENYL TRIAZINE is used as an ingredient in various cosmetic products for its UV protection properties. It helps to prevent skin damage, premature aging, and skin cancer caused by prolonged exposure to the sun. Its compatibility with cosmetic oils and photostability make it a preferred choice for formulating sun protection products in the cosmetics industry.

Flammability and Explosibility

Nonflammable

Safety

Because bemotrizinol is relatively new to the sunscreen market there are few reports or studies available documenting its adverse effects and long term use. Studies to date have shown it to have a good safety profile. It is not significantly absorbed into the skin and rarely causes skin irritation. Unlike some other organic sunscreen agents, in vitro studies show that bemotrizinol does not appear to have hormonal effects. Further long-term human safety studies are required.

Regulations

Bemotrizinol is approved for use in Europe and Australasia. It is marketed under the brand names Tinosorb S and Escalol S. It is currently awaiting FDA approval so is not available in the USA.

InChI:InChI:1S/C38H49N3O5/c1-6-10-12-26(8-3)24-45-30-18-20-32(34(42)22-30)37-39-36(28-14-16-29(44-5)17-15-28)40-38(41-37)33-21-19-31(23-35(33)43)46-25-27(9-4)13-11-7-2/h14-23,26-27,42-43H,6-13,24-25H2,1-5H3

Synthetic route

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

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

2,4-dichloro-6-(4-methoxy-phenyl)-[1,3,5]triazine (90723-86-7) → tinosorb S (187393-00-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / sulfolane / 5 h / 40 - 50 °C 2: sodium carbonate / N,N-dimethyl-formamide / 125 °C View Scheme
Multi-step reaction with 2 steps 1: aluminum (III) chloride / sulfolane / 5 h / 40 - 50 °C 2: sodium carbonate / N,N-dimethyl-formamide / 125 °C View Scheme

methoxybenzene (100-66-3) → tinosorb S (187393-00-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: aluminum (III) chloride / sulfolane / 40 - 60 °C 2: aluminum (III) chloride / sulfolane / 5 h / 40 - 50 °C 3: sodium carbonate / N,N-dimethyl-formamide / 125 °C View Scheme
Multi-step reaction with 3 steps 1: aluminum (III) chloride / sulfolane / 40 - 60 °C 2: aluminum (III) chloride / sulfolane / 5 h / 40 - 50 °C 3: sodium carbonate / N,N-dimethyl-formamide / 125 °C View Scheme

tinosorb S (187393-00-6) + cucurbituril (80262-44-8) → 2C36H36N24O12*C38H49N3O5

Conditions	Yield
at 20 - 47℃; for 3h; neat (no solvent);	38%

Upstream product

• 90723-86-7 2,4-dichloro-6-(4-methoxy-phenyl)-[1,3,5]triazine 
• 108-46-3 recorcinol 
• 123-04-6 3-(chloromethyl)heptane 
• 1440-00-2 4-[4-(2,4-dihydroxyphenyl)-6-(4-methoxyphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol 
• 18908-66-2 3-bromomethylheptane 
• 100-66-3 methoxybenzene 

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.

Preparation method of high-purity bis-ethyl hexyloxyphenol methoxyphenyl triazine

The invention particularly discloses a preparation method of high-purity bis-ethyl hexyloxyphenol methoxyphenyl triazine. The preparation method comprises the following steps: S1, adding 2, 4-dichloro-6-(4-methoxyphenyl)-1, 3, 5-triazine and 3-ethylhexyloxyphenol into a reaction container, performing mixing, then adding an organic solvent and a catalyst, and fully reacting to obtain a reaction liquid; and S2, adding water to quench the reaction liquid in the step S1, and carrying outoil phase water washing, desolvation, recrystallization, filtration and drying to obtain the high-purity bis-ethyl hexyloxyphenol methoxyphenyl triazine. As the number of alkyl groups in the 3-ethylhexyloxyphenol is fixed, the production of monoalkylated products and trialkylated products can be greatly reduced, and target products with higher purity can be obtained; in addition, the catalyst is added into a reaction system in batches, so that the advantages of controlling reaction heat release and enabling raw materials to react completely are achieved; and after the organic solvent is added, gradient heating is carried out, so that the reaction is milder, and the purpose of reducing side reactions is achieved.

Etherification synthesis method of ultraviolet light absorberTinosorb S

The invention discloses an etherification synthesis method of an ultraviolet light absorber Tinosorb S. The etherification synthesis method comprises the following steps: taking 2, 4-bis (2, 4-dihydroxyphenyl)-6-(p-methoxyphenyl)-1, 3, 5-triazine as a raw material, carrying out boronation reaction on the 2, 4-bis (2, 4-dihydroxyphenyl)-6-(p-methoxyphenyl)-1, 3, 5-triazine and boron acetate formed by boric acid and acetic anhydride to obtain a boride of the 2, 4-bis (2, 4-dihydroxyphenyl)-6-(p-methoxyphenyl)-1, 3, 5-triazine, carrying out an etherification reaction with halogenated isooctane in an organic solvent under a weakly alkaline condition, and finally hydrolyzing with sodium hydroxide or potassium hydroxide to obtain an ultraviolet light absorber Tinosorb S product. The synthesis yield can reach 90% or above, and the product purity is 98.5% or above. The synthesis method is high in yield, low in production cost and high in product purity, and the market competitiveness of the product is greatly improved.

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

NOVEL PROCESS FOR THE ETHERIFICATION OF BIS-RESORCINYOL TRIAZINES

The invention relates to an improved process for the manufacture of bis-resorcinyl triazines of formula (I), wherein R1 is hydrogen, a C1-C18alkyl group or a C2-C18alkenyl group and R2 is a C1-C18alkyl group or a C2-C18alkenyl group. (I)

COSMETIC COMPOSITIONS COMPRISING AN ESTER DERIVED FROM 4-CARBOXY-2-PYRROLIDINONE AND A LIPOPHILIC SCREENING AGENT; USE OF SAID DERIVATIVE AS A SOLVENT FOR A BENZOPHENONE LIPOPHILIC SCREENING AGENT

The present invention relates to a composition comprising, in a cosmetically acceptable medium, at least one ester derived from 4-carboxy-2-pyrrolidinone, of formula (I) below: in which: R1 denotes a linear or branched C1-C20 alkyl radical,R2 denotes a linear or branched C1-C20 alkyl radical that may contain a C5-C6 ring, the phenyl radical, the benzyl radical or the phenethyl radical,and at least one benzophenone-type lipophilic UV screening agent. The present invention also relates to the use of at least one ester derived from 4-carboxy-2-pyrrolidinone, of formula (I), as defined above, in a composition comprising, in a cosmetically acceptable medium, at least one benzophenone-type lipophilic UV screening agent, as a solvent for said benzophenone screening agent, in and/or as an agent for improving the solubility of said benzophenone screening agent in said composition or with the aim of improving the sun protection factor.

Ester mixtures and compositions comprising such ester mixtures

The present invention is directed to Mixture of esters according to the general formula (I), R1-C(=O)-O-R2, wherein R1 is an alkyl moiety with 5 to 11 carbon atoms and wherein R2 is a an alkyl moiety with 8 to 1 carbon atoms and wherein the mixture comprises 10 or less than 10 weight-% of ester of the general formula (I), wherein R1 is an alkyl moiety with 9 or more carbon atoms, based on the total amount of esters according to formula (I). The invention is further directed to cosmetic and/or pharmaceutical compositions comprising such esters as well as to processes for the production of such esters.

Ester mixtures and compositions comprising such ester mixtures

The invention is directed to a mixture of esters according to the general formula (1), R1-C(=O)-Q-R2. wherein R1 is an alkyl moiety with 7 to 9 carbon atoms and wherein R2 is a an alkyl moiety with 8 to 10 carbon atoms, wherein the mixture comprises 5 to 60 weight-% of ester of the general formula (I), wherein R1 is an alkyl moiety with 9 carbon atoms, based on the total amount of esters according to formula (I) and/or wherein the mixture comprises 5 to 60 weight-% of ester of the general formula (I), wherein R2 is an alkyl moiety with 10 carbon atoms, based on the total amount of esters according to formula (I). The invention is further directed to cosmetic and/or pharmaceutical compositions comprising such esters as well as to a process for the production of such esters.

ALPHA-AMINO ACID DERIVATIVES FOR IMPROVING SOLUBILITY

The invention relates to the use of α-amino acid derivatives for improving the solubility of poorly soluble substances in water or aqueous solutions and to mixtures and preferred preparations.

UV ABSORBER FORMULATIONS

Disclosed is a UV filter composition comprising (a) an organic UV absorber of formula (1), wherein R1 and R2, independently of one another, are C3-C18alkyl; C2-C18alkenyl; a radical of the formula —CH2—CH(OH)—CH2—O-T1; or R1 and R2 are a radical of the formula (4a); R7 is a direct bond; a straight-chain or branched C1-C4alkylene radical or a radical of the formula (I) or (II); R8, R9 and R10, independently of one another, are C1-C18alkyl; C1-C18alkoxy or a radical of the formula (III); R11 is C1-C5 alkyl; m1 is a number from 1 to 4; p1 is 0; or a number from 1 to 5; A1 is a radical of the formula (1b), (1c) or (1d); R3 is hydrogen; C1-C10alkyl; —(CH2CHR5—O)n1-T2; or —CH2—CH(—OH)—CH2—O-T2; R4 is hydrogen; M; C1-C5alkyl; or —(CH2)m2—O-T3; R5 is hydrogen; or methyl; T1, T2 and T3 independently from each other are hydrogen; or C1-C18alkyl; Q1 is C1-C18alkyl, M is a metal cation; m2 is 1 to 4; and n1 is 1-16, (b) dimethyl capramide, (c) a cosmetically acceptable carrier; and water.