73936-91-1

Basic information

• Product Name: 2-(2H-Benzotriazol-2-yl)-6-(1-methyl-1-phenylethyl)-4-(1,1,3,3-tetramethylbutyl)phenol
• Synonyms: 2-(2H-benzotriazol-2-yl)-6-(1-methyl-1-phenylethy)-4-(1,1,3,3-tetramethylbutyl)-Phenol;TINUVIN 928;2-[2-HYDROXY-3-DIMETHYLBENZYLPHENYL-5-(1,1,3,3-TETRAMETHYLBUTYL)]-2H-BENZOTRIAZOLE;2-6(2H-Benzotriazol-2-yl)-6-(1,1,3,3-tetramethylbutyl)Phenol;2-(2H-BENZOTRIAZOL-2-YL)-6-(1-METHYL-1-PHENYLETHYL)-4-(1,1,3,3-TETRAMETHYLBUTYL)PHENOL;UV ABSORBER-928;Phenol, 2-(2H-benzotriazol-2-yl)-6-(1-methyl-1-phenylethyl)-4-(1,1,3,3-tetramethylbutyl)-;2-[2-Hydroxy-3-dimethylbenzylphenyl-5-(1,1,3,3-tetramethylbutyl)]-2H-benzotriazol
• CAS NO: 73936-91-1
• Molecular Formula: C29H35N3O
• Molecular Weight: 441.6077
• EINECS: 231-545-4
• Mol File: 73936-91-1.mol

Chemical Properties

• Melting Point: 112 °C
• Boiling Point: 555.5±60.0 °C(Predicted)
• Appearance: Slight yellow solid
• Density: 1.07
• Solubility: soluble in Toluene
• PKA: 8.05±0.50(Predicted)
• CAS DataBase Reference: 2-(2H-Benzotriazol-2-yl)-6-(1-methyl-1-phenylethyl)-4-(1,1,3,3-tetramethylbutyl)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2H-Benzotriazol-2-yl)-6-(1-methyl-1-phenylethyl)-4-(1,1,3,3-tetramethylbutyl)phenol(73936-91-1)
• EPA Substance Registry System: 2-(2H-Benzotriazol-2-yl)-6-(1-methyl-1-phenylethyl)-4-(1,1,3,3-tetramethylbutyl)phenol(73936-91-1)

Safety Data

• Hazardous Substances Data: 73936-91-1(Hazardous Substances Data)

Usage

Uses

Used in High-Performance Coatings:
UV absorber-928 is used as a UV stabilizer in high-performance coatings to protect against harmful UV radiation, which can cause degradation and discoloration of the coating. Its broad absorption properties effectively safeguard coatings and other photosensitive materials.
Used in Powder Coating:
UV absorber-928 is used as a UV stabilizer in powder coatings, which are widely used in various industries due to their environmental friendliness and excellent durability. The high solubility and temperature resistance of UV absorber-928 make it particularly suitable for this application.
Used in Industrial and Automotive Coatings:
UV absorber-928 is used as a UV stabilizer in industrial and automotive coatings to provide long-lasting protection against UV-induced degradation and discoloration. Its high environmental durability ensures that the coatings maintain their appearance and performance over time.
Enhanced with HALS Stabilizers:
The performance of UV absorber-928 can be further enhanced when used in combination with a Hindered Amine Light Stabilizer (HALS) stabilizer, such as UV-292 or UV-123. This combination provides superior protection against UV-induced degradation, ensuring the longevity and appearance of the coatings.

Flammability and Explosibility

Notclassified

Synthesis

In a dry argon atmosphere 0.150 g of oxime 5, 0.070 g of 1,2-phenylene diamine 1 and 0.150 ml triethyl-borate are dissolved in 4 ml dry THF and heated for 24 h at 60°C. After a TLC shows consumption of starting oxime the mixture is evaporated to dryness and the resulting residue purified by column chromatography (eluent: hexane - ethyl acetate: 10-1 vol/vol) to give 0.171 g (92 %) of the diazo-amine intermediate 6. Replacing the B(OEt)3 by 2.5 g of basic AI2O3 and the THF by 2 ml of xylene and heating this mixture to 140°C for 48 h gives after the usual work-up 0.089 mg of diazo compound 6 and 0.300 g of starting oxime 5. According the procedure given for the preparation of compound 4 in example 1, triazole 7 is obtained from 0.007 g (0.016 mmol) of intermediate amine 6 and 0.020 g (0.122 mmol) CuSO4 in 100% (0.007 g). In this comparative example, 7.73 equivalents of copper salt are used.

InChI:InChI=1/C29H35N3O/c1-27(2,3)19-28(4,5)21-17-22(29(6,7)20-13-9-8-10-14-20)26(33)25(18-21)32-30-23-15-11-12-16-24(23)31-32/h8-18,33H,19H2,1-7H3

Synthetic route

Conditions	Yield
With ammonium hydroxide; copper(II) sulfate In ethanol; water Solvent; Reagent/catalyst; Reflux;	100%

→ 2-[2'-hydroxy-3'-(α,α-dimethylbenzyl)-5'-(1,1,3,3-tetramethylbutyl)phenyl]benzotriazole (73936-91-1)

Conditions	Yield
In N,N-dimethyl acetamide at 130℃; for 4h;	97%

Upstream product

• 3147-75-9 Cyasorb UV 5411 
• 98-83-9 isopropenylbenzene 
• 95-54-5 1,2-diamino-benzene 
• 73936-80-8 2-cumyl-4-(1,1,3,3-tetramethylbutyl)-phenol 

Downstream Products

• 398474-50-5 2-[2-Hydroxy-3-(4-chlorosulfonyl-α-cumyl)-5-tert-octylphenyl]-2H-benzotriazole 

Relevant articles and documents

NOVEL PROCEDURE FOR THE FORMATION OF 2H-BENZOTRIAZOLE BODIES AND CONGENERS

The present invention relates to a process for the preparation of 2H-benzotriazole compounds and congeners, novel 2H-benzotriazole compounds and congeners and their use as UV absorbers in coatings and bulk plastics.

Preparation method of ultraviolet absorber Tinuvin 928

The invention relates to a method for synthesizing Tinuvin 928 from an ultraviolet absorber UV-329 and alpha-methylstyrene with methanesulfonic acid as catalyst. The method comprises the following steps: adding the UV-329 and methanesulfonic acid into a reactor, heating the reactants to 175 DEG C under the protection of nitrogen, uniformly dropwise adding the alpha-methylstyrene to a position below the surface of the obtained reaction solution by a metering pump for about 6 h, carrying out a reaction at 175-180 DEG C for 0.5-1 h, cooling the obtained reaction material to 95-100 DEG C after thereaction is completed, and standing the cooled reaction material for layering in order to obtain a lower layer methanesulfonic acid and unreacted UV-329 and an upper layer crude product; and washingthe crude product with a 4% aqueous sodium bicarbonate solution twice, washing the crude product with deionized water twice, dissolving the crude product in toluene, decolorizing the obtained solutionwith activated clay, cooling the decolorized solution to crystallize the solution, filtering the solution, and drying obtained crystals at 90-100 DEG C to obtain the yellowish product. The method hasthe advantages of simple synthesis process, easily available raw material UV-329, few side reactions, less generated wastewater, and high yield and high purity of the product.

Body-care and household products and compositions comprising specific sulfur-containing compounds

Disclosed are stabilized body care products, household products, textiles and fabrics which comprise specific sulfur containing compounds. Dyed products and articles are effectively stabilized against color degradation. The products are for example skin-care products, hair-care products, dentifrices, cosmetics, laundry detergents and fabric softeners, non-detergent based fabric care products, household cleaners and textile-care products.

Substituted hexahydro-1,4-diazepin-5-ones and compositions stabilized therewith

The instant invention pertains to white, dyed, dipped, unscented and/or scented candle wax which is effectively stabilized against discoloration and fading by the incorporation therein of a substituted hexahydro-1,4-diazepin-5-ones in combination with a UV absorber and/or an antioxidant. Additionally, some novel substituted hexahydro-1,4-diazepin-5-one compounds are described.

Process for the preparation of benzotriazoles

A process for the preparation of compounds of formula (I): wherein the general symbols are as defined in claim 1, which comprises reacting a compound of formula (V): wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and R18 are as defined in claim 1, and R18 is especially nitro, chlorine or bromine, with an azide compound of formula (IX): wherein M and n are as defined in claim 1, especially with sodium azide.

Processes for the preparation of benzotriazole UV absorbers

Provided is a process for preparing 2H-benzotriazole UV absorbers containing a perfluoroalkyl moiety at the 5-position of the benzo ring, for example a trifluoromethyl group, which involves diazotizing the perfluoroalkyl substituted o-nitroaniline using concentrated sulfuric acid plus sodium nitrite or nitrosylsulfuric acid to form the corresponding monoazobenzene intermediate via the diazonium salt intermediate which is reduced to the corresponding 5-perfluoroalkyl substituted 2H-benzotriazole UV absorber compound by conventional reduction means. Also provided is a novel one-pot, multiphase reaction for the preparation of 2(2-nitrophenylazo) substituted phenols, which are precursors for 2H-benzotriazole UV absorbers.

2-(2-hydroxy-3-α-cumyl-5-nonylor 5-dodecylphenyl)-2H-benzotriazole

Soluble and thermally stable benzotriazole UV absorbers typified by those of formula I STR1 where R1 is hydrogen or chloro, R2 is alkyl or --CH2 CH2 COOR4 where R4 is hydrogen, alkyl or alkyl substituted with hydroxyl, and R3 is α-cumyl, provide excellent light stability protection to electro coat, base coat or clear coat finishes. The new soluble, crystalline form of 2-(2-hydroxy-3-α-cumyl-5-tert-octylphenyl)-2H-benzotriazole is particularly effective.