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2440-22-4 Usage

Characterization

Drometrizole is an ultraviolet light absorber (UVA) of the hydroxyphenyl benzotriazole class, imparting good light stability to a wide variety of polymers.

Applications

Drometrizole?provides ultraviolet protection in a wide variety of polymers including styrene homoand copolymers, engineering plastics such as polyesters and acrylic resins, polyvinyl chloride, and other halogen containing polymers and copolymers (e.g. vinylidenes), acetals and cellulose esters. Elastomers, adhesives, polycarbonate blends, polyurethanes, and some cellulose esters and epoxy materials also benefit from the use of Drometrizole.

Features/benefits

Drometrizole features a strong absorption of ultraviolet radiation in the 300-400 nm region. It also has a high degree of photostability over long periods of light exposure. The high absorbance combined with photostability and the ability to release absorbed energy in non sensitizing ways make Drometrizole an effective stabilizer against the effects of ultraviolet light.

Guidelines for use

The use levels of Drometrizole range between 0.10% and 0.50%, depending on substrate and performance requirements of the final application. Drometrizole can be used alone or in a variety of blends and combinations with Ciba IRGAFOS?, Ciba IRGANOX? and Ciba CHIMASSORB? stabilizers where often a synergistic performance is observed. Drometrizole may react with various heavy metal ions to form salts or complexes. For example, if Drometrizole comes into contact with iron or cobalt ions, colored complexes are formed. Reducing and oxidizing agents used in polymerization and curing processes have no effect on the stability of Drometrizole.

Safety

In accordance with good industrial practice, handle with care and avoid unnecessary personal contact. Protect skin. Prevent contamination of the environment. Avoid dust formation and ignition sources.

Chemical Properties

Light yellow powder

Uses

Different sources of media describe the Uses of 2440-22-4 differently. You can refer to the following data:
1. Drometrizole is an intermediate reactant in the synthesis of UV light absorbers for polyester fibers.
2. An ultraviolet light absorber for stabilizing plastics and other organic materials against discoloration and deterioration.
3. 2(2-Hydroxy-5-methylphenyl)benzotriazol is an UV adsorber for use in plastics, cosmetics, dental materials, acrylic materials, dyes, etc.

Definition

Drometrizole is a member of triazoles.

Application

Intermediate reactant in the synthesis of UV light absorbers for polyester fibersReactant for synthesis of:Benzotriazole UV absorbers with a blocked hydroxy group for us in UV curable paintMaleimide-bound benzotriazole monomer to use for emulsion polymerizationUsed in:Microstereophotolithography and shape memory alloy for fabrication of miniaturized actuatorsPVS and wood / PVC composites as a stabilizerAcrylonitrile-butadiene-styrene as a UV absorber.

Flammability and Explosibility

Notclassified

Check Digit Verification of cas no

The CAS Registry Mumber 2440-22-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,4,4 and 0 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 2440-22:
(6*2)+(5*4)+(4*4)+(3*0)+(2*2)+(1*2)=54
54 % 10 = 4
So 2440-22-4 is a valid CAS Registry Number.

2440-22-4 Well-known Company Product Price

  • Brand
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  • Aldrich

  • (533203)  2-(2-Hydroxy-5-methylphenyl)benzotriazole  97%

  • 2440-22-4

  • 533203-25G

  • 760.50CNY

  • Detail

2440-22-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-(2H-Benzotriazol-2-yl)-p-cresol

1.2 Other means of identification

Product number -
Other names 2-(2H-Benzo[d][1,2,3]triazol-2-yl)-4-methylphenol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2440-22-4 SDS

2440-22-4Synthetic route

4-methyl-2-(2-nitrophenylazo)phenol
1435-71-8

4-methyl-2-(2-nitrophenylazo)phenol

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 50 - 55℃; electrochemical reaction;99.3%
With hydrogen; sodium hydroxide In ethanol; water at 80℃; under 18751.9 Torr; Reagent/catalyst; Autoclave;99.4%
With borane-ammonia complex In toluene at 50℃; for 5h; Reagent/catalyst; Solvent; Temperature;98.6%
2-nitro-2'-hydroxy-5'-methylazobenzene
1435-71-8

2-nitro-2'-hydroxy-5'-methylazobenzene

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

Conditions
ConditionsYield
With sodium hydroxide; thiourea S,S-dioxide In water; isopropyl alcohol for 3h; Heating;98%
With sodium hydroxide In isopropyl alcohol at 85℃; for 24h; Reduction; Cyclization; Irradiation;89%
With sodium hydroxide; bakers' yeast In ethanol 1.) r.t., 30 min, 2.) 80-85 deg C, 40 h;80%
C13H11N3O2

C13H11N3O2

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

Conditions
ConditionsYield
With hydrogenchloride In water; toluene at 70℃; for 2h; Reagent/catalyst; Temperature;92.4%
9-fluorenone
486-25-9

9-fluorenone

D-glucose
50-99-7

D-glucose

2-nitro-2'-hydroxy-5'-methyl-azobenzene
1435-71-8

2-nitro-2'-hydroxy-5'-methyl-azobenzene

A

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

B

2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide
54659-85-7

2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide

Conditions
ConditionsYield
With sodium hydroxide In methanol; waterA 92.1%
B n/a
With sodium hydroxide In methanol; waterA 92.1%
B n/a
2-nitro-2'-hydroxy-5'-methyl-azobenzene
1435-71-8

2-nitro-2'-hydroxy-5'-methyl-azobenzene

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

Conditions
ConditionsYield
With sodium hydroxide; zinc In water at 90℃; for 1.5h;92%
With sodium hydroxide; zinc In ethanol at 100℃; for 4h;85%
With dimethyl amine; palladium-carbon In water; toluene81%
With samarium diiodide In tetrahydrofuran for 0.833333h; Ambient temperature;97 % Spectr.
sodium azide

sodium azide

4-methyl-2-(2-nitrophenylazo)phenol
1435-71-8

4-methyl-2-(2-nitrophenylazo)phenol

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

Conditions
ConditionsYield
In N,N-dimethyl acetamide at 130℃; for 4h;86%
4-methyl-2-(2-nitrophenylazo)phenol
1435-71-8

4-methyl-2-(2-nitrophenylazo)phenol

A

2-Methyl-1H-benzimidazole
615-15-6

2-Methyl-1H-benzimidazole

B

5-methylbenzo[d]oxazol-2(3H)-one
22876-15-9

5-methylbenzo[d]oxazol-2(3H)-one

C

2-nitro-aniline
88-74-4

2-nitro-aniline

D

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

Conditions
ConditionsYield
With carbon monoxide; triethylamine In 1,2-dichloro-benzene at 200℃; under 60800 Torr; for 8h; Further byproducts given;A n/a
B n/a
C 7%
D 82%
2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-2H-benzotriazole
23939-33-5

2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-2H-benzotriazole

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

Conditions
ConditionsYield
With aluminium trichloride; nitromethane In toluene for 7h; Heating;79%
2-nitro-2'-hydroxy-5'-methyl-azobenzene
1435-71-8

2-nitro-2'-hydroxy-5'-methyl-azobenzene

diethylamine
109-89-7

diethylamine

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

Conditions
ConditionsYield
palladium on charcoal catalyst In methanol; phosphoric acid tributyl ester76%
2-Benzotriazol-2-yl-6-(1,1-dimethyl-propyl)-4-methyl-phenol

2-Benzotriazol-2-yl-6-(1,1-dimethyl-propyl)-4-methyl-phenol

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

Conditions
ConditionsYield
With aluminium trichloride; nitromethane In toluene for 7h; Heating;70%
Cu-II-acetylacetonate

Cu-II-acetylacetonate

2-nitro-2'-hydroxy-5'-methyl-azobenzene
1435-71-8

2-nitro-2'-hydroxy-5'-methyl-azobenzene

Trimethylenediamine
109-76-2

Trimethylenediamine

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

Conditions
ConditionsYield
In N-methyl-acetamide64%
2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide
54659-85-7

2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

Conditions
ConditionsYield
With dimethyl amine; aluminum nickel55%
2-Benzotriazol-2-yl-4-methyl-6-(1-methyl-1-phenyl-ethyl)-phenol

2-Benzotriazol-2-yl-4-methyl-6-(1-methyl-1-phenyl-ethyl)-phenol

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

Conditions
ConditionsYield
With aluminium trichloride; nitromethane In toluene for 7h; Heating;70 % Spectr.
4-methyl-2-(2-nitrophenylazo)phenol
1435-71-8

4-methyl-2-(2-nitrophenylazo)phenol

A

2-Methyl-1H-benzimidazole
615-15-6

2-Methyl-1H-benzimidazole

B

N-formyldiethylamine
617-84-5

N-formyldiethylamine

C

5-methylbenzo[d]oxazol-2(3H)-one
22876-15-9

5-methylbenzo[d]oxazol-2(3H)-one

D

2-nitro-aniline
88-74-4

2-nitro-aniline

E

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

Conditions
ConditionsYield
With carbon monoxide; triethylamine In 1,2-dichloro-benzene at 200℃; under 53200 Torr; for 5h; Product distribution; other tertiary amines, var. solvent, var. time;
4-methyl-2-(2-nitrophenylazo)phenol
1435-71-8

4-methyl-2-(2-nitrophenylazo)phenol

A

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

B

3-amino-4-hydroxytoluene
95-84-1

3-amino-4-hydroxytoluene

C

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

Conditions
ConditionsYield
With 2-bromo-2-nitropropane; zinc In methanol; dichloromethane for 21h; Ambient temperature;A n/a
B n/a
C 83 % Chromat.
With hydrogen; sodium hydroxide In water; isopropyl alcohol at 14.84℃; under 760.051 Torr; Reagent/catalyst;
2-nitro-2'-hydroxy-5'-methylazobenzene
1435-71-8

2-nitro-2'-hydroxy-5'-methylazobenzene

A

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

B

2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide
54659-85-7

2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide

C

2-(2-amino-phenylazo)-4-methyl-phenol

2-(2-amino-phenylazo)-4-methyl-phenol

Conditions
ConditionsYield
With sodium hydroxide; hydrogen; nickel In water; isopropyl alcohol at 59.85℃; under 412.533 - 11700.9 Torr; Kinetics; Further Variations:; Pressures; Reagents;
2-nitro-2'-hydroxy-5'-methyl-azobenzene
1435-71-8

2-nitro-2'-hydroxy-5'-methyl-azobenzene

A

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

B

3-amino-4-hydroxytoluene
95-84-1

3-amino-4-hydroxytoluene

C

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

D

2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide
54659-85-7

2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide

Conditions
ConditionsYield
With hydrogen; nickel In water; isopropyl alcohol at 59.85℃; Title compound not separated from byproducts;
4-methyl-2-(2-nitrophenylazo)phenol
1435-71-8

4-methyl-2-(2-nitrophenylazo)phenol

A

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

B

2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide
54659-85-7

2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide

C

4-methyl-2-(2-nitroso-phenylazo)-phenol

4-methyl-2-(2-nitroso-phenylazo)-phenol

D

4-methyl-2-[N'-(2-nitro-phenyl)-hydrazino]-phenol

4-methyl-2-[N'-(2-nitro-phenyl)-hydrazino]-phenol

Conditions
ConditionsYield
With hydrogen; nickel In water; isopropyl alcohol at 1.85℃; under 760 Torr; Product distribution; Kinetics;
C13H11N3O

C13H11N3O

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

Conditions
ConditionsYield
In ethanol at -143.15℃;
p-cresol
106-44-5

p-cresol

NaCl

NaCl

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 73 percent / sodium hydroxide; sodium carbonate / H2O / 20 °C
2: 85 percent / zinc; sodium hydroxide / ethanol / 4 h / 100 °C
View Scheme
2-nitrobenzenediazonium chloride
119-66-4

2-nitrobenzenediazonium chloride

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 73 percent / sodium hydroxide; sodium carbonate / H2O / 20 °C
2: 85 percent / zinc; sodium hydroxide / ethanol / 4 h / 100 °C
View Scheme
2-(1,1-Dimethyl-propyl)-4-methyl-6-(2-nitro-phenylazo)-phenol

2-(1,1-Dimethyl-propyl)-4-methyl-6-(2-nitro-phenylazo)-phenol

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 50 percent / Zn, NaOH / ethanol; H2O / 2 h / Heating
2: 70 percent / AlCl3, CH3NO2 / toluene / 7 h / Heating
View Scheme
9-fluorenone
486-25-9

9-fluorenone

2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide
54659-85-7

2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

Conditions
ConditionsYield
With sodium hydroxide; paraformaldehyde In methanol; water
With sodium hydroxide; paraformaldehyde In methanol; water
2-nitro-2'-hydroxy-5'-methyl-azobenzene
1435-71-8

2-nitro-2'-hydroxy-5'-methyl-azobenzene

copper diacetate
142-71-2

copper diacetate

Trimethylenediamine
109-76-2

Trimethylenediamine

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene; water; isopropyl alcohol; toluene
piperidine
110-89-4

piperidine

copper-II-acetylacetonate

copper-II-acetylacetonate

2-nitro-2'-hydroxy-5'-methyl-azobenzene
1435-71-8

2-nitro-2'-hydroxy-5'-methyl-azobenzene

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene; water
4-methyl-2-(2-nitrophenylazo)phenol
1435-71-8

4-methyl-2-(2-nitrophenylazo)phenol

A

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

B

3-amino-4-hydroxytoluene
95-84-1

3-amino-4-hydroxytoluene

C

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

D

2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide
54659-85-7

2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide

Conditions
ConditionsYield
With hydrogen at 60℃; under 18751.9 Torr;
With 20% Ni/γ-Al2O3; hydrogen; triethylamine In toluene at 120℃; under 18751.9 Torr; Flow reactor;
4-methyl-2-(2-nitrophenylazo)phenol
1435-71-8

4-methyl-2-(2-nitrophenylazo)phenol

A

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

B

2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide
54659-85-7

2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide

Conditions
ConditionsYield
With hydrogen at 60℃; under 18751.9 Torr;
4-methyl-2-(2-nitrophenylazo)phenol
1435-71-8

4-methyl-2-(2-nitrophenylazo)phenol

A

tetrahydro-2-(2-hydroxy-5-methylphenyl)benzotriazole
50467-25-9

tetrahydro-2-(2-hydroxy-5-methylphenyl)benzotriazole

B

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

C

2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide
54659-85-7

2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide

Conditions
ConditionsYield
With hydrogen at 60℃; under 18751.9 Torr;
diethylamine
109-89-7

diethylamine

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

2-(2H-benzotriazol-2-yl)-6-((diethylamino)methyl)-4-methylphenol
103597-49-5

2-(2H-benzotriazol-2-yl)-6-((diethylamino)methyl)-4-methylphenol

Conditions
ConditionsYield
With paraformaldehyde In butan-1-ol99%
With paraformaldehyde In butan-1-ol99%
With paraformaldehyde In butan-1-ol99%
With paraformaldehyde In butan-1-ol96.9%
1-dodecene
112-41-4

1-dodecene

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

2-(2-Hydroxy-3-dodecyl-5-methylphenyl)-2H-benzotriazole

2-(2-Hydroxy-3-dodecyl-5-methylphenyl)-2H-benzotriazole

Conditions
ConditionsYield
With active clay 22B at 160℃; for 2h; Inert atmosphere;97.7%
formaldehyd
50-00-0

formaldehyd

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

2-(2'-hydroxy-3'-chloromethyl-5'-methylphenyl)benzotriazole
18260-27-0

2-(2'-hydroxy-3'-chloromethyl-5'-methylphenyl)benzotriazole

Conditions
ConditionsYield
With hydrogenchloride; acetic acid at 60℃; for 10h;96%
With hydrogenchloride; sulfuric acid; acetic acid In water at 90℃; for 6h;95%
With hydrogenchloride; sulfuric acid In acetic acid at 90℃; for 6h;95%
With hydrogenchloride; acetic acid; zinc(II) chloride at 80℃; for 12h;
acetic anhydride
108-24-7

acetic anhydride

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

2-(2H-1,2,3-benzotriazol-2-yl)-4-methylphenyl acetate
69698-20-0

2-(2H-1,2,3-benzotriazol-2-yl)-4-methylphenyl acetate

Conditions
ConditionsYield
With sulfuric acid Heating;95.1%
Stage #1: acetic anhydride; 2-(2-Hydroxy-5-methylphenyl)benzotriazole With sulfuric acid at 20℃; for 1h;
Stage #2: for 1h; Heating;
94%
With dmap; triethylamine In tetrahydrofuran Inert atmosphere;47.22 g
With dmap; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;
benzyl bromide
100-39-0

benzyl bromide

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

C20H17N3O

C20H17N3O

Conditions
ConditionsYield
With potassium carbonate In acetone at 70℃; for 8h; Heating / reflux;92%
2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

2-(2'-hydroxy-3'-bromo-5'-methylphenyl)benzotriazole
54408-68-3

2-(2'-hydroxy-3'-bromo-5'-methylphenyl)benzotriazole

Conditions
ConditionsYield
With bromine In 1,2-dichloro-ethane at 20℃; for 8h;92%
formaldehyd
50-00-0

formaldehyd

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

6,6'-bis-benzotriazol-2-yl-4,4'-dimethyl-2,2'-methanediyl-bis-phenol
30653-05-5

6,6'-bis-benzotriazol-2-yl-4,4'-dimethyl-2,2'-methanediyl-bis-phenol

Conditions
ConditionsYield
Stage #1: formaldehyd; 2-(2-Hydroxy-5-methylphenyl)benzotriazole With diethylamine In butan-1-ol at 95 - 105℃; for 24h;
Stage #2: With sodium methylate In o-xylene at 140 - 150℃; for 10h; Solvent;
90.4%
water
7732-18-5

water

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

zinc(II) chloride
7646-85-7

zinc(II) chloride

[Zn(hmbt)2(H2O)2]

[Zn(hmbt)2(H2O)2]

Conditions
ConditionsYield
for 4h; Reflux;87%
2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

2-(2H-1,2,3-benzotriazol-2-yl)-4-methyl-6-(2-methylprop-2-enyl)phenol
98809-58-6

2-(2H-1,2,3-benzotriazol-2-yl)-4-methyl-6-(2-methylprop-2-enyl)phenol

Conditions
ConditionsYield
With N,N-dimethyl-aniline; triethylamine In butanone at 80 - 180℃; Product distribution / selectivity; Claisen rearrangement; Inert atmosphere; Molecular sieve;86%
bis-triphenylphosphine-palladium(II) chloride
13965-03-2

bis-triphenylphosphine-palladium(II) chloride

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

[Pd(PPh3)(hmbt)Cl]
1552277-81-2

[Pd(PPh3)(hmbt)Cl]

Conditions
ConditionsYield
In dichloromethane for 48h; Reflux;86%
silver perchlorate

silver perchlorate

triphenylphosphine
603-35-0

triphenylphosphine

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

[Ag(PPh3)(hmbt)]

[Ag(PPh3)(hmbt)]

Conditions
ConditionsYield
With potassium hydroxide In methanol; water for 3h; Darkness;86%
benzoyl chloride
98-88-4

benzoyl chloride

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

benzoic acid 2-(benzotriazol-2-yl)-4-methylphenyl ester

benzoic acid 2-(benzotriazol-2-yl)-4-methylphenyl ester

Conditions
ConditionsYield
With pyridine for 2h; Heating;85%
aluminum (III) chloride In dichloromethane for 2h; Reflux;
[ReOBr3(triphenylarsine)2]
19271-56-8, 136173-40-5

[ReOBr3(triphenylarsine)2]

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

acetonitrile
75-05-8

acetonitrile

[ReOBr2(2-(2-hydroxy-5-methylphenyl)benzotriazolato)(AsPh3)]*MeCN

[ReOBr2(2-(2-hydroxy-5-methylphenyl)benzotriazolato)(AsPh3)]*MeCN

Conditions
ConditionsYield
In acetonitrile ReOBr3(AsPh3)2 added to 2-(2-hydroxy-5-methylphenyl)benzotriazole in MeCN; refluxed for 2 h; allowed to cool to room temp.; pptd. by reducing in vol.; filtered; dried in air; elem. anal.;85%
1-(2-aminoethyl)piperidine
27578-60-5

1-(2-aminoethyl)piperidine

formaldehyd
50-00-0

formaldehyd

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

C35H38N8O2
1400879-39-1

C35H38N8O2

Conditions
ConditionsYield
In toluene for 48h; Inert atmosphere; Reflux;85%
zirconium(IV) tetraisopropoxide 2-propanol
14717-56-7

zirconium(IV) tetraisopropoxide 2-propanol

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

C44H62N6O8Zr2
1491152-50-1

C44H62N6O8Zr2

Conditions
ConditionsYield
In toluene at 20℃; Schlenk technique; Inert atmosphere;85%
niobium pentachloride
10026-12-7

niobium pentachloride

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

C13H10Cl4N3NbO

C13H10Cl4N3NbO

Conditions
ConditionsYield
Stage #1: niobium pentachloride; 2-(2-Hydroxy-5-methylphenyl)benzotriazole In toluene at 0℃; Inert atmosphere; Schlenk technique; Glovebox;
Stage #2: In toluene at 20℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox;
85%
2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

2-(2'-hydroxy-5'-methyl-3'-nitrophenyl)-2H-benzotriazole
36325-72-1

2-(2'-hydroxy-5'-methyl-3'-nitrophenyl)-2H-benzotriazole

Conditions
ConditionsYield
With nitric acid In acetic acid at 70℃; for 0.166667h;84%
zirconium(IV) chloride
10026-11-6

zirconium(IV) chloride

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

C26H20Cl2N6O2Zr
1491152-60-3

C26H20Cl2N6O2Zr

Conditions
ConditionsYield
Stage #1: 2-(2-Hydroxy-5-methylphenyl)benzotriazole With sodium hydride In tetrahydrofuran at 20℃; for 5h; Schlenk technique; Inert atmosphere;
Stage #2: zirconium(IV) chloride In toluene at -24℃; Schlenk technique; Inert atmosphere;
84%
morpholine
110-91-8

morpholine

formaldehyd
50-00-0

formaldehyd

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

C18H20N4O2

C18H20N4O2

Conditions
ConditionsYield
In neat (no solvent) Reflux;84%
tris(triphenylphosphine)ruthenium(II) chloride
15529-49-4, 41756-81-4

tris(triphenylphosphine)ruthenium(II) chloride

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

[Ru(PPh3)(hmbt)2Cl]

[Ru(PPh3)(hmbt)2Cl]

Conditions
ConditionsYield
In methanol for 2h; Reflux;83%
potassium tetrachloropalladate(II)
10025-98-6

potassium tetrachloropalladate(II)

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

[Pd(hmbt)2]
1254251-47-2

[Pd(hmbt)2]

Conditions
ConditionsYield
With potassium hydroxide In methanol; water at 45℃; for 2h;83%

2440-22-4Relevant articles and documents

Reductive cyclization of o-nitrophenylazobenzenes to 2-aryl-2H- benzotriazoles by SmI2

Kim, Byeong Hyo,Kim, Sun Kyong,Lee, Yoon Seok,Jun, Young Moo,Baik, Woonphil,Lee, Byung Min

, p. 8303 - 8306 (1997)

In a mild reaction with SmI2, ortho-nitro substituted phenylazobenzenes have been converted into 2-aryl-2H-benzotriazoles.

Hydrogenation of Substituted Benzenes Containing Nitro and Azo Groups over Skeletal Nickel in Aqueous Solutions of 2-Propanol

An’, Khoang,Belova, A. V.,Lefedova, O. V.,Nemtseva, M. P.

, p. 720 - 724 (2020/04/24)

Abstract: An analysis is made of the kinetic characteristics of the hydrogenation of 4-nitro- and 2-nitro-2'-hydroxy-5'-methylazobenzenes, 4-nitroaniline and 4-aminoazobenzene over skeletal nickel in neutral azeotropic 2-propanol–water mixture and in the same solvent in the presence of acetic acid or sodium hydroxide. It is found that the selectivity of the hydrogenation of these isomers to the intermediate products depends on the composition and nature of the solvent, and is determined by the rate of reactive group conversion. Compared to the process in the presence of sodium hydroxide, which suppresses the route leading to the predominant hydrogenation of the nitro group, the contribution from the transformation of azo group is considerably greater in the hydrogenation of 4-nitro-2'-hydroxy-5'-methylazobenzene in the presence of acetic acid. Adding a base to the solvent during the hydrogenation of 2-nitro-2'-hydroxy-5'-methylazobenzene accelerates the rate of nitro group conversion and the intramolecular cyclization of the intermediate compound, increasing the selectivity towards the products containing the benzotriazole cycle (particularly 2-(2-hydroxy-5-methylphenyl)benzotriazole-N-oxide). The almost linear correlation between the selectivity of the catalytic hydrogenation of isomers of nitro-2'-hydroxy-5'-methylazobenzene and the kinetic characteristics of the hydrogenation of nitro and azo groups in compounds containing a single reactive substituent at different values of medium’s pH is estimated.

A benzo triazole ultraviolet absorbing agent preparation method (by machine translation)

-

Paragraph 0044-0057, (2018/06/15)

The invention discloses a benzo triazole ultraviolet absorbing agent preparation method, including the raw material compound and alkali is dissolved in the solvent, is configured to raw material is added to the reaction device; then the Fe3 O4 /Catalyst is added to the raw material liquid in the graphene, access hydrogen, keeping the pressure 0.1 - 5 mpa, temperature 40 - 120 °C; in the reaction process using high performance liquid chromatography to real-time monitoring of the reaction solution, after the reaction, cooling, the restoration of normal pressure and recovering the catalyst after treatment, be benzo triazole ultraviolet absorbent. The method of this invention simple process, environmental protection, low cost, mild reaction conditions, product yield and quality is high, is suitable for industrial production, Fe used therein3 O4 /Graphene catalyst economic and environmental protection, stable properties, is recycled. (by machine translation)

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