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
• Article Data: 38

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

Description

Bemotrizinol, or bis-ethylhexyloxyphenol methoxyphenyl triazine, is an organic UV filter found in over-the-counter sunscreen products. It primarily absorbs UV-A rays. Compared to older broad-spectrum chemical agents, bemotrizinol is more more fat soluble (oil soluble in cosmetic oils) to aid in efficacy and broad-spectrum activity. It is claimed to be photostable, which increases its onset of action and its efficiency in providing protection against UV-rays upon topical application. Bemotrizinol is commonly marketed as Tinosorb S and Escalol S.

Uses

Bemotrizinol is a broad-spectrum UV absorber, absorbing both UVA and UVB. Bemotrizinol is added to various sunscreens to absorb UV rays.

Brand name

Tinosorb S (Ciba Specialty Chemicals).

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

• 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 
• 90723-86-7 2,4-dichloro-6-(4-methoxy-phenyl)-[1,3,5]triazine 
• 100-66-3 methoxybenzene 
• 18908-66-2 3-bromomethylheptane 
• 108-46-3 recorcinol 

Relevant articles and documents

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.

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.

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)