10096-91-0

Basic information

• Product Name: Phenol, 2-(2H-benzotriazol-2-yl)-
• Synonyms: Phenol,o-2H-benzotriazol-2-yl- (7CI,8CI); 2-(2-Hydroxyphenyl)benzotriazole;2-(2H-Benzotriazol-2-yl)phenol; 2-(2'-Hydroxyphenyl)-2H-benzotriazole;2-(2'-Hydroxyphenyl)benzotriazole; 2-(o-Hydroxyphenyl)-2H-benzotriazole;2-(o-Hydroxyphenyl)benzotriazole; CGL 900
• CAS NO: 10096-91-0
• Molecular Formula: C₁₂H₉N₃O
• Molecular Weight: 211.21936
• Mol File: 10096-91-0.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Phenol, 2-(2H-benzotriazol-2-yl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol, 2-(2H-benzotriazol-2-yl)-(10096-91-0)
• EPA Substance Registry System: Phenol, 2-(2H-benzotriazol-2-yl)-(10096-91-0)

Safety Data

• Hazardous Substances Data: 10096-91-0(Hazardous Substances Data)

Synthetic route

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%

2-(2'H-benzotriazol-2'-yl)-4,6-di-tert-butylphenol (3846-71-7) → 2-(2-Hydroxyphenyl)-2H-benzotriazole (10096-91-0)

Conditions	Yield
With aluminium trichloride; nitromethane In toluene for 7h; Heating;	86%

2-(2-methoxyphenyl)-2H-benzo[d][1,2,3]triazole (40756-56-7) → 2-(2-Hydroxyphenyl)-2H-benzotriazole (10096-91-0)

Conditions	Yield
With hydrogen bromide In acetic acid for 3h; Heating;	85%
With hydrogen bromide for 16h; Heating;	80%

2-(2'H-benzotriazol-2'-yl)-6-t-butyl-4-t-octylphenol → 2-(2-Hydroxyphenyl)-2H-benzotriazole (10096-91-0)

Conditions	Yield
With aluminium trichloride; nitromethane In toluene for 7h; Heating;	81%

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%

2-(2'H-benzotrizol-2'-yl)-6-t-butyl-4-(α,α-dimethylbenzyl)phenol (102116-82-5) → 2-(2'H-benzotriazol-2'-yl)-6-t-butylphenol (34074-96-9) + 2-(2'H-benzotriazol-2'-yl)-4-(α,α-dimethylbenzyl)phenol (15989-00-1) + 2-(2-Hydroxyphenyl)-2H-benzotriazole (10096-91-0)

Conditions	Yield
With aluminium trichloride; nitromethane In toluene for 96h; Ambient temperature;	A n/a B 43% C n/a
With aluminium trichloride; nitromethane In toluene for 96h; Ambient temperature; Title compound not separated from byproducts;	A n/a B 43% C n/a

2-(2H'-benzotriazol-2'-yl)-4-t-butyl-6-(α,α-dimethylbenzyl)phenol (102116-79-0) → 2-(5-tert-butyl-2-hydroxyphenyl)benzotriazole (3147-76-0) + 2-(2-Hydroxyphenyl)-2H-benzotriazole (10096-91-0) + 2-(2'H-benzotriazol-2'-yl)-6-(α,α-dimethylbenzyl)phenol

Conditions	Yield
With aluminium trichloride; nitromethane In toluene for 7h; Heating;	A 27 % Spectr. B 22 % Spectr. C 22%
With aluminium trichloride; nitromethane In toluene for 7h; Heating; Title compound not separated from byproducts;	A 27 % Spectr. B 22 % Spectr. C 34 % Spectr.

2-(2'H-benzotriazol-2'-yl)-4,6-di-tert-butylphenol (3846-71-7) → 2-(5-tert-butyl-2-hydroxyphenyl)benzotriazole (3147-76-0) + 2-(2'H-benzotriazol-2'-yl)-6-t-butylphenol (34074-96-9) + 2-(2-Hydroxyphenyl)-2H-benzotriazole (10096-91-0)

Conditions	Yield
With aluminium trichloride; nitromethane In toluene for 7h; Heating;	A 29 % Spectr. B 10 % Spectr. C 50 % Spectr.

tinuvin 328 (25973-55-1) → 2-(2-Hydroxyphenyl)-2H-benzotriazole (10096-91-0) + 2-(2'H-benzotriazol-2'-yl)-6-t-pentylphenol + 2-(2'H-benzotriazol-2'-yl)-4-t-pentylphenol

Conditions	Yield
With aluminium trichloride; nitromethane In toluene for 7h; Heating;	A 59 % Spectr. B 9 % Spectr. C 25 % Spectr.

2-nitro-aniline (88-74-4) → 2-(2-Hydroxyphenyl)-2H-benzotriazole (10096-91-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) aq. HCl, NaNO2, 2.) aq. NaOH / 1.) 0 deg C, 2.) CH3OH, 0 - 5 deg C, 30 min 2: 85 percent / Zn, NaOH / ethanol; H2O / 2 h / Heating 3: AlCl3, CH3NO2 / toluene / 96 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: 1.) aq. HCl, NaNO2, 2.) aq. NaOH / 1.) 0 deg C, 2.) CH3OH, 0 - 5 deg C, 30 min 2: 48 percent / Zn, NaOH / ethanol; H2O / 2 h / Heating 3: 22 percent Spectr. / AlCl3, CH3NO2 / toluene / 7 h / Heating View Scheme

2-tert-Butyl-6-(2-nitro-phenylazo)-4-(1,1,3,3-tetramethyl-butyl)-phenol → 2-(2-Hydroxyphenyl)-2H-benzotriazole (10096-91-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 48 percent / Zn, NaOH / ethanol; H2O / 2 h / Heating 2: 81 percent / AlCl3, CH3NO2 / toluene / 7 h / Heating View Scheme

2-tert-Butyl-4-(1-methyl-1-phenyl-ethyl)-6-(2-nitro-phenylazo)-phenol (102116-73-4) → 2-(2-Hydroxyphenyl)-2H-benzotriazole (10096-91-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / Zn, NaOH / ethanol; H2O / 2 h / Heating 2: AlCl3, CH3NO2 / toluene / 96 h / Ambient temperature View Scheme

4-tert-Butyl-2-(1-methyl-1-phenyl-ethyl)-6-(2-nitro-phenylazo)-phenol (73936-85-3) → 2-(2-Hydroxyphenyl)-2H-benzotriazole (10096-91-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 48 percent / Zn, NaOH / ethanol; H2O / 2 h / Heating 2: 22 percent Spectr. / AlCl3, CH3NO2 / toluene / 7 h / Heating View Scheme

2-methoxy-phenylamine (90-04-0) → 2-(2-Hydroxyphenyl)-2H-benzotriazole (10096-91-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 51 percent / acetic acid / Ambient temperature 2: 65 percent / 4N NaOH, thiourea dioxide / ethanol / 0.5 h / 80 °C 3: 85 percent / HBr / acetic acid / 3 h / Heating View Scheme

2-methoxy-2'nitroazobenzene (114461-92-6) → 2-(2-Hydroxyphenyl)-2H-benzotriazole (10096-91-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / 4N NaOH, thiourea dioxide / ethanol / 0.5 h / 80 °C 2: 85 percent / HBr / acetic acid / 3 h / Heating View Scheme

o-nitronitrosobenzene (612-29-3) → 2-(2-Hydroxyphenyl)-2H-benzotriazole (10096-91-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 51 percent / acetic acid / Ambient temperature 2: 65 percent / 4N NaOH, thiourea dioxide / ethanol / 0.5 h / 80 °C 3: 85 percent / HBr / acetic acid / 3 h / Heating View Scheme

5-(2-methoxyphenyl)-1-(2-nitrophenyl)tetrazole (78411-58-2) → 2-(2-Hydroxyphenyl)-2H-benzotriazole (10096-91-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / nitrobenzene / 0.5 h / Heating 2: 80 percent / HBr / 16 h / Heating View Scheme

2-(2-Hydroxyphenyl)-2H-benzotriazole (10096-91-0) → 3,3'-bis-(2H-benzotriazol-2-yl)-1,1'-biphenyl-2,2'-diol

Conditions	Yield
With iron(III) chloride In dichloromethane; water

Upstream product

• 25973-55-1 tinuvin 328 
• 88-74-4 2-nitro-aniline 
• 78411-58-2 5-(2-methoxyphenyl)-1-(2-nitrophenyl)tetrazole 
• 114461-92-6 2-methoxy-2'nitroazobenzene 
• 73936-85-3 4-tert-Butyl-2-(1-methyl-1-phenyl-ethyl)-6-(2-nitro-phenylazo)-phenol 
• 102116-73-4 2-tert-Butyl-4-(1-methyl-1-phenyl-ethyl)-6-(2-nitro-phenylazo)-phenol 
• 102116-79-0 2-(2H'-benzotriazol-2'-yl)-4-t-butyl-6-(α,α-dimethylbenzyl)phenol 
• 102116-82-5 2-(2'H-benzotrizol-2'-yl)-6-t-butyl-4-(α,α-dimethylbenzyl)phenol 
• 3846-71-7 2-(2'H-benzotriazol-2'-yl)-4,6-di-tert-butylphenol 
• 3147-75-9 Cyasorb UV 5411 
• 40756-56-7 2-(2-methoxyphenyl)-2H-benzo[d][1,2,3]triazole 
• 612-29-3 o-nitronitrosobenzene 
• 90-04-0 2-methoxy-phenylamine 

Relevant articles and documents

Preparation of Some 2-(Methoxyphenyl)-2H-benzotriazoles and the Corresponding Hydroxyphenyl Compounds

The reaction of several substituted o-nitronitrosobenzenes with o- and p-anisidine, and 2,4-dimethoxyaniline in acetic acid gives in good yield the corresponding o-nitroazobenzenes which are readily reduced with thiourea dioxide (formamidinesulfinic acid) to the corresponding 2-(methoxyphenyl)-2H-benzotriazoles, demethylation of which furnished the corresponding 2-(hydroxyphenyl)-2H-benzotriazoles.Demethylation of the dimethoxy derivatives was best accomplished with boron tribromide in methylene chloride, the methoxy group located ortho to the benzotriazole ring beingdemethylated more readily than is the para-methoxy group.The reaction of 0-nitroazobenzenes containing a methoxy group with hydrobromic acid in acetic acid results in cleavage of the azo bond and also partial bromination to give o-nitroaniline and some of its brominated derivatives.

New Synthesis of Benzotriazole Photostabilizers

1-(2-Nitrophenyl)-5-aryltetrazoles and 1-aryl-5-(2-nitrophenyl)tetrazoles are converted into 2-arylbenzotriazoles by the action of heat, the former reacting much faster than the latter.By appropriate use of methoxyl groups, useful benzotriazole ultraviolet absorbers may be synthesized conveniently by this method.