Conditions | Yield |
---|---|
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
2-(2-Hydroxy-5-methylphenyl)benzotriazole
Conditions | Yield |
---|---|
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% |
2-(2-Hydroxy-5-methylphenyl)benzotriazole
Conditions | Yield |
---|---|
With hydrogenchloride In water; toluene at 70℃; for 2h; Reagent/catalyst; Temperature; | 92.4% |
9-fluorenone
D-glucose
2-nitro-2'-hydroxy-5'-methyl-azobenzene
A
2-(2-Hydroxy-5-methylphenyl)benzotriazole
B
2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; water | A 92.1% B n/a |
With sodium hydroxide In methanol; water | A 92.1% B n/a |
2-nitro-2'-hydroxy-5'-methyl-azobenzene
2-(2-Hydroxy-5-methylphenyl)benzotriazole
Conditions | Yield |
---|---|
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; toluene | 81% |
With samarium diiodide In tetrahydrofuran for 0.833333h; Ambient temperature; | 97 % Spectr. |
Conditions | Yield |
---|---|
In N,N-dimethyl acetamide at 130℃; for 4h; | 86% |
4-methyl-2-(2-nitrophenylazo)phenol
A
2-Methyl-1H-benzimidazole
B
5-methylbenzo[d]oxazol-2(3H)-one
C
2-nitro-aniline
D
2-(2-Hydroxy-5-methylphenyl)benzotriazole
Conditions | Yield |
---|---|
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
2-(2-Hydroxy-5-methylphenyl)benzotriazole
Conditions | Yield |
---|---|
With aluminium trichloride; nitromethane In toluene for 7h; Heating; | 79% |
2-nitro-2'-hydroxy-5'-methyl-azobenzene
diethylamine
2-(2-Hydroxy-5-methylphenyl)benzotriazole
Conditions | Yield |
---|---|
palladium on charcoal catalyst In methanol; phosphoric acid tributyl ester | 76% |
2-(2-Hydroxy-5-methylphenyl)benzotriazole
Conditions | Yield |
---|---|
With aluminium trichloride; nitromethane In toluene for 7h; Heating; | 70% |
2-nitro-2'-hydroxy-5'-methyl-azobenzene
Trimethylenediamine
2-(2-Hydroxy-5-methylphenyl)benzotriazole
Conditions | Yield |
---|---|
In N-methyl-acetamide | 64% |
2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide
2-(2-Hydroxy-5-methylphenyl)benzotriazole
Conditions | Yield |
---|---|
With dimethyl amine; aluminum nickel | 55% |
2-(2-Hydroxy-5-methylphenyl)benzotriazole
Conditions | Yield |
---|---|
With aluminium trichloride; nitromethane In toluene for 7h; Heating; | 70 % Spectr. |
4-methyl-2-(2-nitrophenylazo)phenol
A
2-Methyl-1H-benzimidazole
B
N-formyldiethylamine
C
5-methylbenzo[d]oxazol-2(3H)-one
D
2-nitro-aniline
E
2-(2-Hydroxy-5-methylphenyl)benzotriazole
Conditions | Yield |
---|---|
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
A
1,2-diamino-benzene
B
3-amino-4-hydroxytoluene
C
2-(2-Hydroxy-5-methylphenyl)benzotriazole
Conditions | Yield |
---|---|
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
A
2-(2-Hydroxy-5-methylphenyl)benzotriazole
B
2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide
Conditions | Yield |
---|---|
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
A
1,2-diamino-benzene
B
3-amino-4-hydroxytoluene
C
2-(2-Hydroxy-5-methylphenyl)benzotriazole
D
2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide
Conditions | Yield |
---|---|
With hydrogen; nickel In water; isopropyl alcohol at 59.85℃; Title compound not separated from byproducts; |
4-methyl-2-(2-nitrophenylazo)phenol
A
2-(2-Hydroxy-5-methylphenyl)benzotriazole
B
2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide
Conditions | Yield |
---|---|
With hydrogen; nickel In water; isopropyl alcohol at 1.85℃; under 760 Torr; Product distribution; Kinetics; |
2-(2-Hydroxy-5-methylphenyl)benzotriazole
Conditions | Yield |
---|---|
In ethanol at -143.15℃; |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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-(2-Hydroxy-5-methylphenyl)benzotriazole
Conditions | Yield |
---|---|
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
2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide
2-(2-Hydroxy-5-methylphenyl)benzotriazole
Conditions | Yield |
---|---|
With sodium hydroxide; paraformaldehyde In methanol; water | |
With sodium hydroxide; paraformaldehyde In methanol; water |
2-nitro-2'-hydroxy-5'-methyl-azobenzene
copper diacetate
Trimethylenediamine
2-(2-Hydroxy-5-methylphenyl)benzotriazole
Conditions | Yield |
---|---|
In 5,5-dimethyl-1,3-cyclohexadiene; water; isopropyl alcohol; toluene |
piperidine
2-nitro-2'-hydroxy-5'-methyl-azobenzene
2-(2-Hydroxy-5-methylphenyl)benzotriazole
Conditions | Yield |
---|---|
In 5,5-dimethyl-1,3-cyclohexadiene; water |
4-methyl-2-(2-nitrophenylazo)phenol
A
1,2-diamino-benzene
B
3-amino-4-hydroxytoluene
C
2-(2-Hydroxy-5-methylphenyl)benzotriazole
D
2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide
Conditions | Yield |
---|---|
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
A
2-(2-Hydroxy-5-methylphenyl)benzotriazole
B
2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide
Conditions | Yield |
---|---|
With hydrogen at 60℃; under 18751.9 Torr; |
4-methyl-2-(2-nitrophenylazo)phenol
A
tetrahydro-2-(2-hydroxy-5-methylphenyl)benzotriazole
B
2-(2-Hydroxy-5-methylphenyl)benzotriazole
C
2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide
Conditions | Yield |
---|---|
With hydrogen at 60℃; under 18751.9 Torr; |
diethylamine
2-(2-Hydroxy-5-methylphenyl)benzotriazole
2-(2H-benzotriazol-2-yl)-6-((diethylamino)methyl)-4-methylphenol
Conditions | Yield |
---|---|
With paraformaldehyde In butan-1-ol | 99% |
With paraformaldehyde In butan-1-ol | 99% |
With paraformaldehyde In butan-1-ol | 99% |
With paraformaldehyde In butan-1-ol | 96.9% |
Conditions | Yield |
---|---|
With active clay 22B at 160℃; for 2h; Inert atmosphere; | 97.7% |
formaldehyd
2-(2-Hydroxy-5-methylphenyl)benzotriazole
2-(2'-hydroxy-3'-chloromethyl-5'-methylphenyl)benzotriazole
Conditions | Yield |
---|---|
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
2-(2-Hydroxy-5-methylphenyl)benzotriazole
2-(2H-1,2,3-benzotriazol-2-yl)-4-methylphenyl acetate
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 70℃; for 8h; Heating / reflux; | 92% |
2-(2-Hydroxy-5-methylphenyl)benzotriazole
2-(2'-hydroxy-3'-bromo-5'-methylphenyl)benzotriazole
Conditions | Yield |
---|---|
With bromine In 1,2-dichloro-ethane at 20℃; for 8h; | 92% |
formaldehyd
2-(2-Hydroxy-5-methylphenyl)benzotriazole
6,6'-bis-benzotriazol-2-yl-4,4'-dimethyl-2,2'-methanediyl-bis-phenol
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
for 4h; Reflux; | 87% |
2-(2-Hydroxy-5-methylphenyl)benzotriazole
3-Chloro-2-methylpropene
2-(2H-1,2,3-benzotriazol-2-yl)-4-methyl-6-(2-methylprop-2-enyl)phenol
Conditions | Yield |
---|---|
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
2-(2-Hydroxy-5-methylphenyl)benzotriazole
[Pd(PPh3)(hmbt)Cl]
Conditions | Yield |
---|---|
In dichloromethane for 48h; Reflux; | 86% |
Conditions | Yield |
---|---|
With potassium hydroxide In methanol; water for 3h; Darkness; | 86% |
Conditions | Yield |
---|---|
With pyridine for 2h; Heating; | 85% |
aluminum (III) chloride In dichloromethane for 2h; Reflux; |
[ReOBr3(triphenylarsine)2]
2-(2-Hydroxy-5-methylphenyl)benzotriazole
acetonitrile
Conditions | Yield |
---|---|
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
formaldehyd
2-(2-Hydroxy-5-methylphenyl)benzotriazole
C35H38N8O2
Conditions | Yield |
---|---|
In toluene for 48h; Inert atmosphere; Reflux; | 85% |
zirconium(IV) tetraisopropoxide 2-propanol
2-(2-Hydroxy-5-methylphenyl)benzotriazole
C44H62N6O8Zr2
Conditions | Yield |
---|---|
In toluene at 20℃; Schlenk technique; Inert atmosphere; | 85% |
Conditions | Yield |
---|---|
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
2-(2'-hydroxy-5'-methyl-3'-nitrophenyl)-2H-benzotriazole
Conditions | Yield |
---|---|
With nitric acid In acetic acid at 70℃; for 0.166667h; | 84% |
zirconium(IV) chloride
2-(2-Hydroxy-5-methylphenyl)benzotriazole
C26H20Cl2N6O2Zr
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
In neat (no solvent) Reflux; | 84% |
tris(triphenylphosphine)ruthenium(II) chloride
2-(2-Hydroxy-5-methylphenyl)benzotriazole
Conditions | Yield |
---|---|
In methanol for 2h; Reflux; | 83% |
potassium tetrachloropalladate(II)
2-(2-Hydroxy-5-methylphenyl)benzotriazole
[Pd(hmbt)2]
Conditions | Yield |
---|---|
With potassium hydroxide In methanol; water at 45℃; for 2h; | 83% |
Assay: 99% min (HPLC)
Transmittance: 440nm: 97% min
500nm: 98% min
Ash content: 0.3% max
1.Introduction of Ultraviolet Absorbent UV-P
UV-P (CAS NO.2440-22-4), its Synonyms are 2-(2'-Hydroxy-5'-methylphenyl)benzotriazole ; 2-(2H-Benzotriazol-2-yl)-4-methylphenol ; Benazol P ; Drometrizole ; Phenol, 2-(2H-benzotriazol-2-yl)-4-methyl- ; UV Absorber-1 ; 2-(2-Hydroxy-5-methylphenyl)-2H-benzotriazole ; 2-(2-Hydroxy-5-methylphenyl)benzotriazole ; p-Cresol, 2-(2H-benzotriazol-2-yl)- .
2.Properties of Ultraviolet Absorbent UV-P
(1) XLogP3 4.3 (2) H-Bond Donor 1 (3) H-Bond Acceptor 3
(4) Rotatable Bond Count 1 (5) Tautomer Count 3 (6) Exact Mass 225.090212
(7) MonoIsotopic Mass 225.090212 (8) Topological Polar Surface Area 50.9
(9) Heavy Atom Count 17 (10) Complexity 259 (11)Covalently-Bonded Unit Count 1
(12) Feature 3D Acceptor Count 2 (13) Feature 3D Donor Count 1 (14) Feature 3D Ring Count 3
(15) Effective Rotor Count 1 (16) Conformer Sampling RMSD 0.6 (17) CID Conformer Count 2
3.Structure descriptors of Ultraviolet Absorbent UV-P
IUPAC Name: 2-(benzotriazol-2-yl)-4-methylphenol
InChI: InChI=1S/C13H11N3O/c1-9-6-7-13(17)12(8-9)16-14-10-4-2-3-5-11(10)15-16/
h2-8,17H,1H3
InChIKey: MCPKSFINULVDNX-UHFFFAOYSA-N
Canonical SMILES : CC1=CC(=C(C=C1)O)N2N=C3C=CC=CC3=N2
4.Uses of Ultraviolet Absorbent UV-P
UV-P is a benzotriazole type UV absorber. It is used for polyvinylchloride , styrenic polymer ( acrylonitrile butadiene , high impact polystyrene , general purpose polystyrene ), unsturated polyester elastomers and adhesives , acrylic resins , polycarbonate , polyurethane , and cellulose ester .
5.Toxicity data of Ultraviolet Absorbent UV-P
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | oral | 6500mg/kg (6500mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 10(3), Pg. 49, 1966. |
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