25973-55-1

Basic information

• Product Name: 2-(2H-Benzotriazol-2-yl)-4,6-ditertpentylphenol
• Synonyms: 2-(3',5'-di-t-aMyl-2'-hydroxyphenyl) benzotriazole;2-(3,5-Di-tert-amyl-2-hydroxyphenyl)benzotriazole;HRsorb-328;2-(2-Hydroxy-3,5-dipenryl-phenyl) benzotriazole;UV-328;2-(2H-Benzotriazol-2-yl)-4,6-di-tert-amylphenol;UV ABSORBER UV-328;2-(2H-benzotriaziol-2-yl)-4,6-Di-Tert-Pentylphenol
• CAS NO: 25973-55-1
• Molecular Formula: C₂₂H₂₉N₃O
• Molecular Weight: 351.49
• EINECS: 247-384-8
• Product Categories: Industrial/Fine Chemicals;Polymer Additives;Polymer Science;Stabilizers
• Mol File: 25973-55-1.mol
• Article Data: 33

Chemical Properties

• Melting Point: 80-83°C
• Boiling Point: 469.1 °C at 760 mmHg
• Flash Point: 237.5 °C
• Appearance: /
• Density: 1.08 g/cm³
• Vapor Pressure: 2.01E-09mmHg at 25°C
• Refractive Index: 1.575
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Sonicated)
• PKA: 8.85±0.50(Predicted)
• CAS DataBase Reference: 2-(2H-Benzotriazol-2-yl)-4,6-ditertpentylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2H-Benzotriazol-2-yl)-4,6-ditertpentylphenol(25973-55-1)
• EPA Substance Registry System: 2-(2H-Benzotriazol-2-yl)-4,6-ditertpentylphenol(25973-55-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-53-48/22
• Safety Statements: 26-36-61-22-53
• WGK Germany: 2
• Hazardous Substances Data: 25973-55-1(Hazardous Substances Data)

Usage

Consumer Uses

This substance is used in the following products: coating products, air care products, adhesives and sealants, lubricants and greases, polishes and waxes and washing & cleaning products. Other release to the environment of this substance is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners), outdoor use, indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters) and outdoor use in close systems with minimal release (e.g. hydraulic liquids in automotive suspension, lubricants in motor oil and break fluids).

Properties

UV-328 has a?melting point?of 80-86?°C, a?vapor pressure?of 4,6·10?5?Pa (20?°C) and a?water solubility?of < 0,001 g·l?1?(20?°C).

Description

UV-328 (2-(2H-Benzotriazol-2-yl)-4,6-ditertpentylphenol) is a chemical compound that belongs to the phenolic benzotriazoles. It is a UV filter that is used as an antioxidant for plastics.

Uses

Different sources of media describe the Uses of 25973-55-1 differently. You can refer to the following data:
1. 2-(2H-Benzotriazol-2-yl)-4,6-di-tert-pentylphenol is an ultraviolet light absorber (UVA) of the hydroxyphenylbenzotriazole class, which imparts outstanding light stability to plastics and other organic substrates.
2. UV-328 is a class of benzotriazole derivatives that can potentially be used as corrosion inhibitors in heat resistant fluids in aircraft, brake fluids in automobiles and for other industrial cooling systems.

Application

UV-328 is a light stabilizer for a variety of plastics and other organic substrates. Its use is recommended for the stabilization of styrene homopolymers and copolymers, acrylic polymers, unsaturated polyesters, polyvinyl chloride, polyolefins, polyurethanes, polyacetals, polyvinyl butyral, elastomers and adhesives.It protects polymers and organic pigments from UV radiation and helps maintain the original appearance and physical integrity of moldings, films, sheets and fibers during outdoor weathering. The application concentration is 0.1-1 %.UV-328 is recommended for applications such as automotive coatings, industrial coatings, commercial inks such as wood stains or do-it-yourself inks.

General Description

2-(2H-Benzotriazol-2-yl)-4,6-di-tert-pentylphenol (UV-328) is an ultraviolet (UV) stabilizer with a phenolic group connected to the benzotriazole structure. These phenolic groups facilitate the absorption of UV light. UV-328 is mainly used in as a light stabilizer for coating and as an additive for industrial polymers.

InChI:InChI=1/C22H29N3O/c1-7-21(3,4)15-13-16(22(5,6)8-2)20(26)19(14-15)25-23-17-11-9-10-12-18(17)24-25/h9-14,26H,7-8H2,1-6H3

Synthetic route

aqueous hypophosphorous acid + 2-Nitro-2'-hydroxy-3',5'-di-tert-pentyl-azobenzene → tinuvin 328 (25973-55-1)

Conditions	Yield
With hydrogenchloride; hydrogen; tert-butylamine In methanol	99%

C22H29N3O2 → tinuvin 328 (25973-55-1)

Conditions	Yield
In isopropyl alcohol at 83 - 85℃; for 3h; Temperature;	98.29%

2,4-bis(1",1"-dimethylpropyl)-6-(2'-nitrophenylazo)phenol → tinuvin 328 (25973-55-1)

Conditions	Yield
With borane-ammonia complex In toluene at 50℃; for 5h;	96.4%
With sodium hydroxide; thiourea dioxide In ethanol at 85 - 90℃; for 1h;	80%
With sodium hydroxide; lithium perchlorate In tetrahydrofuran; water at 20℃; Cyclization; Electrolysis;	92 % Chromat.
With hydrogen In cyclohexane at 180℃; under 3750.38 Torr;
Multi-step reaction with 2 steps 1: 2,3-Dichloro-1,4-naphthoquinone; sodium hydroxide / isopropyl alcohol / 2 h / 42 - 45 °C / Inert atmosphere 2: isopropyl alcohol / 3 h / 83 - 85 °C View Scheme

sodium azide + 2,4-bis(1",1"-dimethylpropyl)-6-(2'-nitrophenylazo)phenol → tinuvin 328 (25973-55-1)

Conditions	Yield
In DMF (N,N-dimethyl-formamide) at 130℃; for 13h;	93.9%

2-(2'-hydroxy-3',5'-di-t-pentylphenyl)benzotriazole oxynitride → tinuvin 328 (25973-55-1)

Conditions	Yield
With platinum on activated charcoal; hydrogen In methanol; toluene at 50 - 75℃; under 3750.38 - 6000.6 Torr; Reagent/catalyst; Solvent; Autoclave;	91.7%
With hydrogenchloride; zinc In water; toluene Reflux;

2-(2'H-benzotriazol-2'-yl)-4,6-bis(1",1"-dimethylpropyl)phenol 1'-oxide (94109-79-2) → tinuvin 328 (25973-55-1)

Conditions	Yield
aluminum nickel In water; hydrogen	90.3%
With sodium hydroxide; bakers' yeast In ethanol 1.) r.t., 30 min, 2.) 80-85 deg C, 30 h;	86%

2-Nitro-2'-hydroxy-3',5'-di-tert-pentyl-azobenzene → tinuvin 328 (25973-55-1)

Conditions	Yield
With sodium hydroxide; zinc In water at 90℃; for 0.5h;	87%
	85%
aluminum nickel In water; toluene	82%
With samarium diiodide In tetrahydrofuran for 2.7h; Ambient temperature;	85 % Spectr.
With hydrogenchloride; sulfuric acid; hydrogen; hydrazine hydrate; N-butylamine; pyrographite In methanol; 5,5-dimethyl-1,3-cyclohexadiene; water

2,4-Bis-(1,1-dimethyl-propyl)-6-(2-nitro-phenylazo)-phenol → tinuvin 328 (25973-55-1)

Conditions	Yield
With sodium hydroxide; bakers' yeast In ethanol 1.) r.t., 30 min, 2.) 80-85 deg C, 36 h;	85%
With sodium hydroxide In isopropyl alcohol at 85℃; for 24h; Reduction; Cyclization; Irradiation;	67%
Multi-step reaction with 2 steps 1: 87 percent / aq. NaOH, bakers' yeast / ethanol / 1.) r.t., 30 min, 2.) 80-85 deg C, 3.5 h 2: 86 percent / aq. NaOH, bakers' yeast / ethanol / 1.) r.t., 30 min, 2.) 80-85 deg C, 30 h View Scheme

2,4-bis(1",1"-dimethylpropyl)-6-(2'-nitrophenylazo)phenol → 2-amino-4,6-bis(1,1-dimethylpropyl)phenol (23786-32-5) + 1,2-diamino-benzene (95-54-5) + tinuvin 328 (25973-55-1)

Conditions	Yield
With 2-bromo-2-nitropropane; zinc In methanol; dichloromethane for 3.5h; Ambient temperature;	A n/a B n/a C 71 % Chromat.

2,3-Dichloro-1,4-naphthoquinone (117-80-6) + 2-Nitro-2'-hydroxy-3',5'-di-tert-pentyl-azobenzene → tinuvin 328 (25973-55-1)

Conditions	Yield
With sodium hydroxide; sodium hydrogensulfite In water; isopropyl alcohol

9-fluorenone (486-25-9) + D-glucose (50-99-7) + 2-Nitro-2'-hydroxy-3',5'-di-tert-pentyl-azobenzene → tinuvin 328 (25973-55-1)

Conditions	Yield
With sodium hydroxide In methanol; water

2-Chloronitrobenzene (88-73-3) → tinuvin 328 (25973-55-1)

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: water; ethanol / 3 h / 10 °C / pH 7.2 - 7.8 / Alkaline conditions 4: sodium hydroxide; formaldehyd / isopropyl alcohol / Reflux 5: zinc; hydrogenchloride / water; toluene / Reflux View Scheme

2-nitro-aniline (88-74-4) → tinuvin 328 (25973-55-1)

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

2-nitrodiazophenyl hydrochloride → tinuvin 328 (25973-55-1)

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

cyclopentadienylzirconium trichloride + tinuvin 328 (25973-55-1) → [(η5-cyclopentadineyl)ZrCl2(tetrahydrofuran)(2-(2H-benzo[d][1,2,3]triazol-2-yl)-4,6-di-tert-pentylphenol(-1H))]

Conditions	Yield
In tetrahydrofuran (N2); using Schlenk techniques; addn. of CpZrCl3 (1 equiv.) to soln. of 2-(2H-benzo(d)(1,2,3)triazol-2-yl)-4,6-di-tert-pentylphenol (1 equiv.) in THF at room temp., heating at 50°C for 12 h; filtration, condensing of filtrate, keeping at -20°C, crystn.; elem. anal.;	95%

palladium diacetate (3375-31-3) + tinuvin 328 (25973-55-1) → bis[2-(2H-benzotriazol-2-yl)-4,6-di-tert-pentylphenolato]palladium(II)

Conditions	Yield
In tetrahydrofuran at 20℃; for 48h;	92.4%

cyclopentadienylzirconium trichloride + tinuvin 328 (25973-55-1) → [(η5-cyclopentadienyl)2Zr(μ-Cl)3(2-(2H-benzo[d][1,2,3]triazol-2-yl)-4,6-di-tert-pentylphenol(-1H))ZrCl2]

Conditions	Yield
In toluene (N2); using Schlenk techniques; addn. of CpZrCl3 (2 equiv.) to soln. of 2-(2H-benzo(d)(1,2,3)triazol-2-yl)-4,6-di-tert-pentylphenol (1 equiv.) in toluene at room temp., heating at 50°C for 12 h; filtration, crystn. at -20°C, washing with n-hexane; elem. anal.;	86%

trimethylaluminum (75-24-1) + tinuvin 328 (25973-55-1) + phenol (108-95-2) → [Al(OPh)(2-(2H-benzo[d][1,2,3]triazol-2-yl)-4,6-di-tert-pentylphenol(-1H))2]

Conditions

Yield

In toluene (N2); using Schlenk techniques; addn. of soln. of HOC6H2(C5H11)2C6H4N3 in toluene to stirred soln. of AlMe3 in toluene at -78°C; warming to room temp.; reflux for 1 h; removal of solvent (vac.); dissolving in MePh; addn. of phenol; reflux for 1 h; removal of all volatiles under vac., washing with n-hexane 3 times; dissolving in CH2Cl2/hexane; cooling at -20°C for a few ds; crystn.; elem. anal.;

85%

tetrahydrofuran (109-99-9) + titanium tetrachloride (7550-45-0) + tinuvin 328 (25973-55-1) → C26H36Cl3N3O2Ti

Conditions	Yield
In dichloromethane at -78 - 20℃; for 12h; Glovebox; Schlenk technique; Inert atmosphere;	85%

cyclopentadienylzirconium trichloride + tinuvin 328 (25973-55-1) → [(η5-cyclopentadienyl)ZrCl2(2-(2H-benzo[d][1,2,3]triazol-2-yl)-4,6-di-tert-pentylphenol(-1H))]2 (1283647-02-8)

Conditions	Yield
In toluene (N2); using Schlenk techniques; addn. of CpZrCl3 (1 equiv.) to soln. of 2-(2H-benzo(d)(1,2,3)triazol-2-yl)-4,6-di-tert-pentylphenol (1 equiv.) in toluene at room temp., heating at 50°C for 12 h; filtration, crystn. at -20°C, washing with n-hexane; elem. anal.;	84%

titanium tetrachloride (7550-45-0) + tinuvin 328 (25973-55-1) → C44H56Cl6N6O2Ti2

Conditions	Yield
In dichloromethane at -78 - 20℃; for 12h; Glovebox; Schlenk technique; Inert atmosphere;	83%

copper(II) acetate monohydrate (6046-93-1) + tinuvin 328 (25973-55-1) → bis[2-(2H-benzotriazol-2-yl)-4,6-di-tert-pentylphenolato]copper(II)

Conditions	Yield
In ethanol for 1h; Reflux;	83%

tetrakis(dimethylamido)titanium(IV) + tinuvin 328 (25973-55-1) → C48H68N8O2Ti

Conditions	Yield
In dichloromethane at 20 - 50℃; for 12h; Schlenk technique; Glovebox; Inert atmosphere;	81%

niobium pentachloride (10026-12-7) + tinuvin 328 (25973-55-1) → C22H28Cl4N3NbO

Conditions	Yield
Stage #1: niobium pentachloride; tinuvin 328 In toluene at 0℃; Inert atmosphere; Schlenk technique; Glovebox; Stage #2: In toluene at 20℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox;	81%

4-Phenylphenol (92-69-3) + trimethylaluminum (75-24-1) + tinuvin 328 (25973-55-1) → [Al(O(p-C6H4Ph))(2-(2H-benzo[d][1,2,3]triazol-2-yl)-4,6-di-tert-pentylphenol(-1H))2] (1206697-22-4)

Conditions

Yield

In toluene (N2); using Schlenk techniques; addn. of soln. of HOC6H2(C5H11)2C6H4N3 in MePh to stirred soln. of AlMe3 in MePh at -78°C; warming to room temp.; reflux for 1 h; removal of solvent (vac.); dissolving in MePh; addn. of 4-Ph-phenol; reflux for 1 h; removal of all volatiles under vac., washing with n-hexane 3 times; dissolving in CH2Cl2/hexane; cooling at -20°C for a few ds; crystn.; elem. anal.;

80%

titanium(IV) isopropylate (546-68-9) + tinuvin 328 (25973-55-1) → C50H70N6O4Ti

Conditions	Yield
In dichloromethane at 20℃; for 12h; Schlenk technique; Glovebox; Inert atmosphere;	80%

tantalum pentachloride (7721-01-9) + tinuvin 328 (25973-55-1) → C22H28Cl4N3OTa

Conditions	Yield
Stage #1: tantalum pentachloride; tinuvin 328 In toluene at 0℃; Inert atmosphere; Schlenk technique; Glovebox; Stage #2: In toluene at 20℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox;	80%

tinuvin 328 (25973-55-1) → 2-(2-Hydroxyphenyl)-2H-benzotriazole (10096-91-0)

Conditions	Yield
With aluminium trichloride; nitromethane In toluene for 7h; Heating;	79%

zirconium(IV) tetraisopropoxide 2-propanol (14717-56-7) + tinuvin 328 (25973-55-1) → C62H98N6O8Zr2 (1491152-52-3)

Conditions	Yield
In toluene at -24℃; Schlenk technique; Inert atmosphere;	79%

zirconium(IV) tetraisopropoxide 2-propanol (14717-56-7) + tinuvin 328 (25973-55-1) → C88H112N12O4Zr

Conditions	Yield
In toluene at 70℃; for 36h; Schlenk technique; Inert atmosphere;	76%

tetrakis(dimethylamido)zirconium (IV) (19756-04-8) + chloro-trimethyl-silane (75-77-4) + tinuvin 328 (25973-55-1) → [Zr(2-(2H-benzo[d][1,2,3]triazol-2-yl)-4,6-di-tert-pentylphenol(-1H))2Cl2]

Conditions	Yield
In dichloromethane (N2); using Schlenk techniques; addn. of Zr(NMe2)4 (0.5 equiv.) to soln.of C6H4N3C6H2(t-Bu)2OH (1 equiv.) in CH2Cl2 at room temp., heating at 5 0°C for 12 h, filtration, addn. to TMSCl in CH2Cl2 at room temp.,stirring at room temp. for 5 h; removal of solvent under vac., redissolving in CH2Cl2, filtration, condensing, addn. of hexane, crystn. at -20°C, washing with n-hexane; elem. anal.;	75%
In toluene (N2); using Schlenk techniques; tretament of Zr(NMe2)4 (0.5 equiv.) withC6H4N3C6H2(t-Bu)2OH (1 equiv.) in toluene and then addn. of TMSCl in to luene;

copper(II) acetate monohydrate (6046-93-1) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) + tinuvin 328 (25973-55-1) → C44H56CuN6O2*0.5C3H7NO

Conditions	Yield
at 70℃; for 1h;	75%

hafnium(IV) tert-butoxide + tinuvin 328 (25973-55-1) → C88H112HfN12O4

Conditions	Yield
In toluene at 70℃; for 24h; Schlenk technique; Inert atmosphere;	71%

N,N-dimethyl acetamide (127-19-5) + copper(II) acetate monohydrate (6046-93-1) + tinuvin 328 (25973-55-1) → C44H56CuN6O2*0.5C4H9NO

Conditions	Yield
at 70℃; for 1h;	35%

copper(II) bis(trifluoromethanesulfonate) (34946-82-2) + tinuvin 328 (25973-55-1) → bis[2-(2H-benzotriazol-2-yl)-4,6-di-tert-pentylphenolato]copper(II)

Conditions	Yield
Stage #1: tinuvin 328 With triethylamine In toluene; acetonitrile at 20℃; for 0.166667h; Stage #2: copper(II) bis(trifluoromethanesulfonate) In toluene; acetonitrile at 20℃;	23%

Upstream product

• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 52184-19-7 2-Nitro-2'-hydroxy-3',5'-di-tert-pentyl-azobenzene 
• 88-74-4 2-nitro-aniline 
• 88-73-3 2-Chloronitrobenzene 
• 486-25-9 9-fluorenone 
• 50-99-7 D-glucose 
• 52184-19-7 2,4-bis(1,1-dimethylpropyl)-6-(2'-nitrophenylazo)phenol 
• 52184-19-7 2,4-Bis-(1,1-dimethyl-propyl)-6-(2-nitro-phenylazo)-phenol 
• 94109-79-2 2-(2'H-benzotriazol-2'-yl)-4,6-bis(1,1-dimethylpropyl)phenol 1'-oxide 

Downstream Products

• 1206697-22-4 [Al(O(p-C₆H₄Ph))(2-(2H-benzo[d][1,2,3]triazol-2-yl)-4,6-di-tert-pentylphenol(-1H))2] 
• 10096-91-0 2-(2-Hydroxyphenyl)-2H-benzotriazole 

Relevant articles and documents

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