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Bumetrizole
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Name

Bumetrizole

 EINECS 223-445-4
CAS No. 3896-11-5 Density 1.26 g/cm3
PSA 50.94000 LogP 4.38540
Solubility 4μg/L at 20℃ Melting Point 144-147 °C(lit.)
Formula C17H18ClN3O Boiling Point 460.4 °C at 760 mmHg
Molecular Weight 315.802 Flash Point 232.3 °C
Transport Information N/A Appearance powder
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 3896-11-5 (Bumetrizole) Hazard Symbols IrritantXi
Synonyms

p-Cresol,2-tert-butyl-6-(5-chloro-2H-benzotriazol-2-yl)- (7CI,8CI);2-(2-Hydroxy-3-tert-butyl-5-methylphenyl)-5-chloro-2H-benzotriazole;2-(2-Hydroxy-3-tert-butyl-5-methylphenyl)-5-chlorobenzotriazole;2-(2'-Hydroxy-3'-tert-butyl-5'-methylphenyl)-5-chlorobenzotriazole;2-(3-tert-Butyl-2-hydroxy-5-methylphenyl)-5-chloro-2H-benzo-v-triazole;2-(3-tert-Butyl-2-hydroxy-5-methylphenyl)-5-chlorobenzotriazole;2-(3'-tert-Butyl-2'-hydroxy-5'-methylphenyl)-5-chlorobenzotriazole;2-(5-Chloro-2H-benzotriazol-2-yl)-6-(1,1-dimethylethyl)-4-methylphenol;2-[5-Chloro-2H-benzotriazol-2-yl]-4-methyl-6-(tert-butyl)phenol;2-tert-Butyl-6-(5-chloro-2-benzotriazolyl)-4-methylphenol;5-Chloro-2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-2H-benzotriazole;5-Chloro-2-(3-tert-butyl-2-hydroxy-5-methylphenyl)benzotriazole;A-Light;ADKStab LA 36;Cibatex LF;Phenol,2-(5-chloro-2H-benzotriazol-2-yl)-6-(1,1-dimethylethyl)-4-methyl-;

Article Data 27

Bumetrizole Synthetic route

22617-04-5

2-<(4-Chloro-2-nitrophenyl)azo>-6-(1,1-dimethylethyl)-4-methylphenol

A

56750-11-9

2-tert-Butyl-6-(6-chloro-1-oxy-benzotriazol-2-yl)-4-methyl-phenol

B

3896-11-5

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

Conditions
ConditionsYield
With sodium hydroxide; thiourea S,S-dioxide In water; isopropyl alcohol for 3h; Heating;A 0.3%
B 98%

C17H18ClN3O2

3896-11-5

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

Conditions
ConditionsYield
In isopropyl alcohol at 80 - 82℃; for 4h;97.8%
22617-04-5

2-nitro-4-chloro-2'-hydroxy-3'-tert-butyl-5'-methylazobenzene

3896-11-5

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

Conditions
ConditionsYield
With borane-ammonia complex In toluene at 50℃; for 5h;97.4%
Multi-step reaction with 2 steps
1: 77 percent / glucose, 2N NaOH / ethanol / 1 h / Heating
2: 84 percent / Zn, 2N NaOH / ethanol / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: sodium hydroxide; hydrazine hydrate / 5,5-dimethyl-1,3-cyclohexadiene; acetone
2: hydrogen; platinum on activated charcoal / 50 - 75 °C / 3750.38 - 6000.6 Torr / Autoclave
View Scheme
With hydrazine hydrate; sodium hydroxide In toluene at 60℃; for 8h; Temperature;
Multi-step reaction with 2 steps
1: 2,3-Dichloro-1,4-naphthoquinone; sodium hydroxide / isopropyl alcohol / 2 h / 40 - 45 °C / Inert atmosphere
2: isopropyl alcohol / 4 h / 80 - 82 °C
View Scheme

C17H20ClN3O2

3896-11-5

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

Conditions
ConditionsYield
With sodium phosphite; hydrogen; sodium hydroxide at 80℃; under 11251.1 Torr; for 8h; Reagent/catalyst; Pressure; Temperature; Autoclave;94.3%

C17H18ClN3O2

3896-11-5

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

Conditions
ConditionsYield
With platinum on activated charcoal; hydrogen at 50 - 75℃; under 3750.38 - 6000.6 Torr; Autoclave;92.1%

2-Nitro-4-chloro-2'-hydroxy-3'-tert-butyl-5'-methyl-azobenzene

3896-11-5

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

Conditions
ConditionsYield
With sodium hydroxide; zinc In water at 90℃; for 0.5h;92%
22617-04-5

2-<(4-Chloro-2-nitrophenyl)azo>-6-(1,1-dimethylethyl)-4-methylphenol

A

109969-10-0

2-(2-Amino-4-chloro-phenylazo)-6-tert-butyl-4-methyl-phenol

B

56750-11-9

2-tert-Butyl-6-(6-chloro-1-oxy-benzotriazol-2-yl)-4-methyl-phenol

C

3896-11-5

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

Conditions
ConditionsYield
With sodium hydroxide; thiourea S,S-dioxide In methanol; water for 3h; Product distribution; Heating; other solvents, various molar equivalents of thiourea S,S-dioxide and NaOH;A 3%
B 2%
C 91%
With sodium hydroxide; thiourea S,S-dioxide In water; isopropyl alcohol for 3h; Heating;A 2%
B 40%
C 54%
117-80-6

2,3-Dichloro-1,4-naphthoquinone

2-Nitro-4-chloro-2'-hydroxy-3'-tert-butyl-5'-methyl-azobenzene

50-99-7

D-glucose

A

94102-12-2

2-(2-hydroxy-3-t-butyl-5-methylphenyl)-5-chlorobenzotriazole-N-oxide

B

3896-11-5

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

Conditions
ConditionsYield
With sodium hydroxide In methanolA n/a
B 89.5%
56750-11-9

2-tert-Butyl-6-(6-chloro-1-oxy-benzotriazol-2-yl)-4-methyl-phenol

3896-11-5

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

Conditions
ConditionsYield
With sodium hydroxide; zinc In ethanol for 1h; Ambient temperature;84%

2-Nitro-4-chloro-2'-hydroxy-3'-tert-butyl-5'-methyl-azobenzene

Cu-II-acetylacetonate

Cu-II-acetylacetonate

2440-22-4

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

3896-11-5

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

Conditions
ConditionsYield
70%

Bumetrizole Chemical Properties

 
IUPAC Name: 2-tert-Butyl-6-(5-chlorobenzotriazol-2-yl)-4-methylphenol
Molecular Formula: C17H18ClN3O
Molecular Weight: 315.8 g/mol
Canonical SMILES: n1(c2c(c(cc(c2)C)C(C)(C)C)O)nc2ccc(cc2n1)Cl
InChI: InChI=1/C17H18ClN3O/c1-10-7-12(17(2,3)4)16(22)15(8-10)21-19-13-6-5-11(18)9-14(13)20-21/h5-9,22H,1-4H3
EINECS: 223-445-4
Classification Code: Ultraviolet screen
Product Categories: Industrial / Fine Chemicals; Polymer Additives; Polymer Science; Stabilizers
Surface Tension: 43.1 dyne/cm 
Density: 1.26 g/cm3 
Flash Point: 232.3 °C 
Enthalpy of Vaporization: 74.88 kJ/mol 
Boiling Point: 460.4 °C at 760 mmHg 
Melting Point: 144-147 °C(lit.)
Vapour Pressure of Bumetrizole (CAS NO.3896-11-5): 4.24E-09 mmHg at 25 °C

Bumetrizole Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36: Wear suitable protective clothing.
WGK Germany of Bumetrizole (CAS NO.3896-11-5): 1

Bumetrizole Specification

 Bumetrizole (CAS NO.3896-11-5), its Synonyms are 2-(2'-Hydroxy-3'-tert-butyl-5'-methylphenyl)-5-chlorobenzotriazole ; 2-tert-Butyl-6-(5-chloro-2H-benzotriazol-2-yl)-p-cresol ; Bumetrizol ; Bumetrizolum ; Phenol, 2-(5-chloro-2H-benzotriazol-2-yl)-6-(1,1-dimethylethyl)-4-methyl- ; 2-(5-Chloro-2H-benzotriazol-2-yl)-6-(1,1-dimethylethyl)-4-methylp- henol ; 2-(2-Hydroxy-3-tert-butyl-5-methylphenyl)-5-chloro-2H-benzotriazole ; UV-326 .

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