3147-75-9

Basic information

• Product Name: Octrizole
• Synonyms: LABOTEST-BB LT00053579;EUSORB 323;2-(2'-HYDROXY-5'-TERT-OCTYLLPHENYL)BENZOTRIAZOLE;2-(2'-HYDROXY-5'-TERT-OCTYL PHENYL) BENZOTRIAZOLE;2-(2-HYDROXY-5-TERT-OCTYLPHENYL)BENZOTRIAZOLE;2-(2H-BENZOTRIAZOL-2-YL)-4-(1,1,3,3-TETRAMETHYLBUTYL)PHENOL;TINUVIN 329;OCTRIZOLE
• CAS NO: 3147-75-9
• Molecular Formula: C₂₀H₂₅N₃O
• Molecular Weight: 323.43
• EINECS: 221-573-5
• Product Categories: Intermediates of Dyes and Pigments;Industrial/Fine Chemicals;Phenoles and thiophenoles
• Mol File: 3147-75-9.mol
• Article Data: 21

Chemical Properties

• Melting Point: 106-108 °C(lit.)
• Boiling Point: 471.8 °C at 760 mmHg
• Flash Point: 239.2 °C
• Appearance: Slightly yellowish powder
• Density: 1.1 g/cm³
• Vapor Pressure: 1.58E-09mmHg at 25°C
• Refractive Index: 1.584
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 8.07±0.45(Predicted)
• Water Solubility: 2μg/L at 20℃
• CAS DataBase Reference: Octrizole(CAS DataBase Reference)
• NIST Chemistry Reference: Octrizole(3147-75-9)
• EPA Substance Registry System: Octrizole(3147-75-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 1
• Hazardous Substances Data: 3147-75-9(Hazardous Substances Data)

Usage

Characterization

UV-329 is an ultraviolet light absorber (UVA) of the hydroxyphenyl benzotriazole class, which is used as a light stabilizer for plastics and other organic substrates.

Applications

UV-329 is an effective light stabilizer for a variety of plastics and other organic substrates.

Features/benefits

UV-329 protects polymers from UV radiation, helping to preserve the original appearance and physical integrity of molded articles, films, sheets, and fibers during outdoor weathering.

Product forms

UV-329??? Slightly yellow powder UV-329 FL???? Slightly yellow, rodlike granules

Guidelines for use

The use levels of UV-329 range between 0.1 and 1.0 %, depending on substrate and performance requirements of the final application. The product can be used alone or in combination with other additives such as light stabilizers (hindered amines), antioxidants (hindered phenols, phosphites, thiosynergists, hydroxylamines), and other functional stabilizers and additives. The use of UV-329 in combination with hindered amine light stabilizers is particularly noteworthy in that a synergistic performance is often observed. Performance data of UV-329 alone or in combination with other additives are available in selected substrates.

Handling & Safety

UV-329 exhibits a very low order of oral toxicity and does not present any abnormal problems in its handling or general use. Detailed information on handling and any precautions to be observed in the use of the product(s) described in this leaflet can be found in our relevant health and safety information sheet.

Description

The ultraviolet absorber UV-329 is a highly effective anti-aging additive with excellent performance. It is soluble in benzene, styrene lookchem, dichloromethane and cyclohexane, slightly soluble in alcohols, insoluble in water; it can effectively absorb 270- 380 nanometer ultraviolet light; non-flammable, non-explosive, non-toxic, safe and harmless to use.

Uses

Different sources of media describe the Uses of 3147-75-9 differently. You can refer to the following data:
1. UV absorber
2. Ultraviolet screen.

Definition

An UV light absorber.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C20H25N3O/c1-19(2,3)13-20(4,5)14-10-11-18(24)17(12-14)23-21-15-8-6-7-9-16(15)22-23/h6-12,24H,13H2,1-5H3

Synthetic route

C20H25N3O2 → Cyasorb UV 5411 (3147-75-9)

Conditions	Yield
In isopropyl alcohol at 80 - 82℃; for 4h;	97.5%

2-(2'-hydroxy-5'-tert-octylphenyl)nitrodiazobenzene (51656-57-6) → Cyasorb UV 5411 (3147-75-9)

Conditions	Yield
With methanol; Aminoiminomethanesulfinic acid; sodium hydroxide In toluene at 50 - 80℃; for 0.5h; Reagent/catalyst; Solvent; Temperature;	96.4%
With sodium hydroxide; zinc In water; Petroleum ether at 50℃; for 5h;

2-(2-Nitro-phenylazo)-4-(1,1,3,3-tetramethyl-butyl)-phenol (51656-57-6) → Cyasorb UV 5411 (3147-75-9)

Conditions	Yield
With sodium hydroxide; thiourea S,S-dioxide In water; isopropyl alcohol for 3h; Heating;	96%

2-nitro-2-hydroxy-5-tert-octyl-azobenzene → Cyasorb UV 5411 (3147-75-9)

Conditions	Yield
	93%

2-nitro-aniline (88-74-4) + tert-octylphenol (140-66-9) → Cyasorb UV 5411 (3147-75-9)

Conditions	Yield
Stage #1: 2-nitro-aniline With sulfuric acid In water for 0.333333h; Stage #2: With sodium nitrite In water at 0℃; for 2.5h; Cooling with ice; Stage #3: tert-octylphenol Further stages;	90.01%
Multi-step reaction with 2 steps 1.1: sodium nitrite; hydrogenchloride / water / -15 - 5 °C 1.2: 2 h / 0 °C 2.1: zinc; sodium hydroxide / water; Petroleum ether / 5 h / 50 °C View Scheme

C20H25N3O2 → Cyasorb UV 5411 (3147-75-9)

Conditions	Yield
With hydrogenchloride In water; toluene at 70℃; for 2h; Concentration; Temperature; Reagent/catalyst;	89.5%
With hydrogenchloride; zinc In toluene Reflux;	88.2%

2-nitro-2'-hydroxy-5'-tert-octylazobenzene + 2-nitro-2'-hydroxy-5'-tert-butylazobenzene (27959-42-8) → Cyasorb UV 5411 (3147-75-9)

Conditions	Yield
	85%
	85%

2-nitro-2'-hydroxy-5'-tert-octylazobenzene + 2-Nitro-2'-hydroxy-3',5'-di-tert-pentyl-azobenzene → Cyasorb UV 5411 (3147-75-9)

Conditions	Yield
	83.7%

2-nitro-2'-hydroxy-5'-tert-octylazobenzene → Cyasorb UV 5411 (3147-75-9)

Conditions	Yield
With dimethyl amine; palladium-carbon In water; toluene	82.9%

2-nitro-2'-hydroxy-5'-tert-octylazobenzene + 9-fluorenone (486-25-9) → Cyasorb UV 5411 (3147-75-9)

Conditions	Yield
With sodium hydroxide; sulfuric acid; paraformaldehyde In methanol; water
With sodium hydroxide; sulfuric acid; paraformaldehyde In methanol; water

2-Chloronitrobenzene (88-73-3) → Cyasorb UV 5411 (3147-75-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: ammonium hydroxide / 150 - 220 °C / 90009 - 150015 Torr 2: sodium nitrite; hydrogenchloride / water / 1 h / 10 °C 3: sodium hydroxide / water; ethanol / 3 h / 10 °C / pH 7.2-7.8 4: sodium hydroxide; formaldehyd / Reflux 5: zinc; hydrogenchloride / toluene / Reflux View Scheme

2-nitro-aniline (88-74-4) → Cyasorb UV 5411 (3147-75-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium nitrite; hydrogenchloride / water / 1 h / 10 °C 2: sodium hydroxide / water; ethanol / 3 h / 10 °C / pH 7.2-7.8 3: sodium hydroxide; formaldehyd / Reflux 4: zinc; hydrogenchloride / toluene / Reflux View Scheme

2-nitrobenzenediazonium chloride (119-66-4) → Cyasorb UV 5411 (3147-75-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / water; ethanol / 3 h / 10 °C / pH 7.2-7.8 2: sodium hydroxide; formaldehyd / Reflux 3: zinc; hydrogenchloride / toluene / Reflux View Scheme

trifluoromethylsulfonic anhydride (358-23-6) + Cyasorb UV 5411 (3147-75-9) → trifluoromethanesulfonic acid 2-benzotriazol-2-yl-4-(1,1,3,3-tetramethylbutyl)phenyl ester (943024-15-5)

Conditions	Yield
With pyridine In dichloromethane at 20 - 30℃;	100%

diethylamine (109-89-7) + Cyasorb UV 5411 (3147-75-9) → 2-(2-hydroxy-3-diethylaminomethyl-5-tert-octylphenyl)-2H-benzotriazole

Conditions	Yield
With paraformaldehyde In butan-1-ol	99%
With paraformaldehyde In butan-1-ol	99%
With paraformaldehyde In butan-1-ol	99%

formaldehyd (50-00-0) + Cyasorb UV 5411 (3147-75-9) → methylene bis-benzotriazolyl tetramethylbutylphenol (103597-45-1)

Conditions	Yield
Stage #1: formaldehyd; Cyasorb UV 5411 With diethylamine In 1,3,5-trimethyl-benzene at 130℃; for 4h; Stage #2: With sodium methylate In 1,3,5-trimethyl-benzene at 160℃; for 5h; Temperature; Solvent; Reagent/catalyst;	96.3%

dibutylamine (111-92-2) + Cyasorb UV 5411 (3147-75-9) → 2-[2-Hydroxy-3-(di-n-butylaminomethyl)-5-tert-octylphenyl]-2H-benzotriazole

Conditions	Yield
With paraformaldehyde	96%

tetrakis(dimethylamido)zirconium (IV) (19756-04-8) + Cyasorb UV 5411 (3147-75-9) → [(2-(2H-benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol)2(-H)4Zr]

Conditions	Yield
In hexane at 25℃; for 1h; Inert atmosphere;	95%

Cyasorb UV 5411 (3147-75-9) → 2-(2H-benzo[1,2,3]triazol-2-yl)-6-bromo-4-(2,4,4-trimethylpentan-2-yl)phenol

Conditions	Yield
With bromine In dichloromethane at 20℃; for 8h;	95%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In chloroform at 20℃;	91%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In chloroform at 20℃;	91%

water (7732-18-5) + trimethylaluminum (75-24-1) + Cyasorb UV 5411 (3147-75-9) → bis[2-(2H-benzotriazol-2-yl-κN)-4-(1,1,3,3-tetramethylbutyl)phenolato-κO]methylaluminum(III) dihydrate

Conditions	Yield
Stage #1: trimethylaluminum; Cyasorb UV 5411 In hexane; toluene at -78 - 20℃; for 72h; Inert atmosphere; Stage #2: water	95%

p-formaldehyde + Cyasorb UV 5411 (3147-75-9) → methylene bis-benzotriazolyl tetramethylbutylphenol (103597-45-1)

Conditions	Yield
Stage #1: p-formaldehyde; Cyasorb UV 5411 With diethylamine In xylene at 95 - 100℃; for 24h; Stage #2: With sodium methylate In methanol at 145 - 150℃; for 10h;	92%

tetra(isopropoxy)hafnium isopropanol (1070655-38-7) + Cyasorb UV 5411 (3147-75-9) → [(2-(2H-benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol)4Hf]

Conditions	Yield
In hexane at 30℃; for 12h; Inert atmosphere;	92%

Cyasorb UV 5411 (3147-75-9) + isopropenylbenzene (98-83-9) → 2-[2'-hydroxy-3'-(α,α-dimethylbenzyl)-5'-(1,1,3,3-tetramethylbutyl)phenyl]benzotriazole (73936-91-1)

Conditions	Yield
With methanesulfonic acid at 175 - 180℃; for 6.5h; Temperature; Inert atmosphere;	90.3%

chloroform (67-66-3) + water (7732-18-5) + dimethylaluminum chloride (1184-58-3) + Cyasorb UV 5411 (3147-75-9) → bis[2-(2H-benzotriazol-2-yl-κN)-4-(1,1,3,3-tetramethylbutyl)phenolato-κO]chloroaluminum(III)*H2O*CHCl3

Conditions	Yield
Stage #1: dimethylaluminum chloride; Cyasorb UV 5411 In tetrahydrofuran; hexane at -78 - 20℃; for 72h; Inert atmosphere; Stage #2: chloroform; water	90%

Cyasorb UV 5411 (3147-75-9) → 2-(2-Hydroxyphenyl)-2H-benzotriazole (10096-91-0)

Conditions	Yield
With aluminium trichloride; nitromethane In toluene for 7h; Heating;	88%

nonaethyleneglycol mono(p-toluenesulfonyl) ether (62573-11-9) + Cyasorb UV 5411 (3147-75-9) → nonaethylene glycol mono(2-(benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenyl) ether

Conditions	Yield
Stage #1: Cyasorb UV 5411 With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1h; Stage #2: nonaethyleneglycol mono(p-toluenesulfonyl) ether In tetrahydrofuran; mineral oil at 20℃; for 24h;	87%

zirconium(IV) tetraisopropoxide 2-propanol (14717-56-7) + Cyasorb UV 5411 (3147-75-9) → [(2-(2H-benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol)2(-H)Zr(OiPr)2]

Conditions	Yield
In hexane at 0℃; for 2h; Inert atmosphere;	85%

bis-(dipropylamino)methane (10333-53-6) + Cyasorb UV 5411 (3147-75-9) → methylene bis-benzotriazolyl tetramethylbutylphenol (103597-45-1)

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide In neat (no solvent) at 130℃; under 100 Torr; for 2h; Temperature;	80.9%
With sodium hydroxide at 120 - 160℃; under 100 Torr; for 4h; Time;	70.3%

Cyasorb UV 5411 (3147-75-9) → difluoro-[2-(2H-benzotriazol-2-yl-κN)-4-(1,1,3,3-tetramethylbutyl)-phenolate-κO]-boron (1198179-86-0)

Conditions	Yield
With boron trifluoride diethyl etherate In toluene at -78℃; Inert atmosphere; Reflux;	80%

boron trifluoride diethyl etherate (109-63-7) + Cyasorb UV 5411 (3147-75-9) → difluoro-[2-(2H-benzotriazol-2-yl-κN)-4-(1,1,3,3-tetramethylbutyl)-phenolate-κO]-boron (1198179-86-0)

Conditions	Yield
In toluene benzotriazole-compd. dissolved in dried toluene, cooled to -78°C under N2, B-compd. added dropwise, refluxed for 6 h, cooled; evaporated in vac., crystallized from CHCl3, elem. anal.;	80%

tetra(isopropoxy)hafnium isopropanol (1070655-38-7) + Cyasorb UV 5411 (3147-75-9) → [(2-(2H-benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol)2Hf(OiPr)2]

Conditions	Yield
In hexane at 0℃; for 3h; Inert atmosphere;	80%

titanium(IV) isopropylate (546-68-9) + Cyasorb UV 5411 (3147-75-9) → [(μ-2-(2H-benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenolate)Ti(OiPr)3]2 (1416561-82-4)

Conditions	Yield
In hexane at 20℃; for 18h; Inert atmosphere;	77%

formaldehyd (50-00-0) + diisopropylamine (108-18-9) + Cyasorb UV 5411 (3147-75-9) → 2-(2H-benzotriazol-2-yl)-6-((diisopropylamino)-methyl)-4-(2,4,4-trimethylpentan-2-yl)phenol

Conditions	Yield
With triethylamine for 48h; Mannich Aminomethylation; Inert atmosphere; Reflux;	76%

formaldehyd (50-00-0) + Cyasorb UV 5411 (3147-75-9) + N,N`-dimethylethylenediamine (110-70-3) → C46H62N8O2

Conditions	Yield
In ethanol for 72h; Mannich Aminomethylation; Reflux;	76%
In ethanol Reflux;

Upstream product

• 51656-57-6 2-(2-Nitro-phenylazo)-4-(1,1,3,3-tetramethyl-butyl)-phenol 
• 52184-19-7 2-Nitro-2'-hydroxy-3',5'-di-tert-pentyl-azobenzene 
• 486-25-9 9-fluorenone 
• 27959-42-8 2-nitro-2'-hydroxy-5'-tert-butylazobenzene 
• 88-73-3 2-Chloronitrobenzene 
• 88-74-4 2-nitro-aniline 
• 119-66-4 2-nitrobenzenediazonium chloride 
• 140-66-9 tert-octylphenol 
• 51656-57-6 2-(2'-hydroxy-5'-tert-octylphenyl)nitrodiazobenzene 

Downstream Products

• 185155-06-0 2,2'-dihydroxy-3-(2H-benzotriazol-2-yl)-3'-(4,6-diphenyl-s-triazin-2-yl)-5-tert-octyl-6'-hexyloxy-diphenylmethane 
• 116043-76-6 6-allyl-2-(2H-1,2,3-benzotriazol-2-yl)-4-(t-octyl)phenol 
• 10096-91-0 2-(2-Hydroxyphenyl)-2H-benzotriazole 
• 73936-91-1 2-[2'-hydroxy-3'-(α,α-dimethylbenzyl)-5'-(1,1,3,3-tetramethylbutyl)phenyl]benzotriazole 
• 103597-45-1 methylene bis-benzotriazolyl tetramethylbutylphenol 

Relevant articles and documents

ANTI-BLUE LIGHT COMPOUND, PREPARATION METHOD AND APPLICATION THEREOF

Disclosed is a blue light absorbing compound, its preparation method and use. The compound has high stability and is suitable for high temperature processing conditions as well as outdoor application. A method of covalently bonding a blue light absorbing compound with an ultraviolet light absorbing compound for increasing its stability is also provided. The compound is capable of absorbing or blocking ultraviolet light (UVA, UVB) and blue light to protect eyes. But long-wavelength blue light can be absorbed diminishingly, so that the transmitted light has a particularly good visual experience.

Novel polycyclic compound

The invention provides a novel polycyclic compound as well as a synthesis method and application thereof. The compound of the present invention includes a plurality of carbocyclic and/or heterocyclicstructures having visible or fluorescent light emitting groups and covalently bonded to at least one ultraviolet and/or visible (blue) light absorbing group to provide stability. The compound providedby the invention can be used as a light conversion agent, a dye, a pigment, a fluorescent agent and an ultraviolet light or blue light absorbent, and can be applied to optical films, agricultural films, optical discs (disks), optical lenses, goggles, skin care, cosmetics, illumination, coatings, adhesives, light stabilizers, panels and other products.

Preparation method of ultraviolet absorbent UV - 329 (by machine translation)

The invention provides a preparation method, UV - 329, of an ultraviolet absorber. The method comprises the following steps: performing ammonification, diazotization, coupling, one-step reduction, two-step reduction reaction and post-treatment to prepare 2 - (2 '- hydroxyl -5' - t-octylphenyl) benzotriazole product by o-nitrochlorobenzene. To the method, by ammonia water with a concentration 10%~25%, o-nitrochlorobenzene is subjected to diazotization reaction with nitrite to generate a diazonium salt, the diazotization reaction does not need to be carried out in a strong acid medium, and byproduct ammonia water of the product in the company is comprehensively utilized. The reduction closed-loop process of the intermediate azo product adopts 2-step reduction method, the strong reducing agent is prevented from directly reducing the azo double bond to the amine, impurity generation, product purity, and yield. (by machine translation)