2-hydroxy-4-methoxybenzhydrol
Benzophenone-3
Conditions | Yield |
---|---|
With bismuth (III) nitrate pentahydrate; cellulose supported copper(0); oxygen In acetonitrile at 60℃; for 0.5h; | 97% |
With triethylamine; pyridinium chlorochromate In dichloromethane at 20℃; |
Conditions | Yield |
---|---|
With sodium carbonate at 160 - 170℃; for 10h; | 94% |
With tetrabutylammomium bromide; sodium carbonate In methanol at 170 - 175℃; under 22502.3 - 30003 Torr; Temperature; Reagent/catalyst; Pressure; Large scale; | 86.1% |
Conditions | Yield |
---|---|
With tetrabutyl-ammonium chloride; sodium carbonate In tert-butyl methyl ether; water; chlorobenzene at 100℃; under 2250.23 Torr; for 2h; Temperature; Solvent; Reagent/catalyst; Pressure; Autoclave; | 91% |
Conditions | Yield |
---|---|
With beryllium(II) chloride In toluene for 3h; Heating; | 90% |
With boron trichloride In dichloromethane at 0℃; Inert atmosphere; | |
With aluminum (III) chloride In dichloromethane at 20℃; |
Conditions | Yield |
---|---|
With aluminium trichloride In 1,2-dichloro-ethane 1) 0-5 deg C -> r.t., 2 h 2) reflux, 1h; | 85% |
With aluminium trichloride; zinc(II) chloride |
Conditions | Yield |
---|---|
boron trichloride In benzene for 10h; Heating; | 85% |
Benzophenone-3
Conditions | Yield |
---|---|
With dipotassium hydrogenphosphate; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; triphenylphosphine In tetrahydrofuran at 25℃; for 8h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation; | 85% |
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cesium acetate; silver carbonate In N,N-dimethyl-formamide at 120℃; for 24h; Sealed tube; | 82% |
Conditions | Yield |
---|---|
With piperidine In ethanol at 80℃; Green chemistry; | 82% |
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 0 - 20℃; for 17h; | 81% |
With caesium carbonate In acetonitrile at 0 - 20℃; |
Conditions | Yield |
---|---|
at 100℃; for 22h; Friedel-Crafts Acylation; Glovebox; | 80% |
Conditions | Yield |
---|---|
With potassium carbonate at 100℃; under 2250.23 Torr; for 8h; Catalytic behavior; Suzuki-Miyaura Coupling; Autoclave; | 74% |
Conditions | Yield |
---|---|
With pyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(I) bromide In tert-Amyl alcohol at 130℃; for 24h; Sealed tube; chemoselective reaction; | 70% |
Conditions | Yield |
---|---|
With [(C6H6)(PCy3)(CO)RuH]+*BF4−; potassium carbonate; triphenylphosphine In chlorobenzene at 110℃; for 12h; Kinetics; Reagent/catalyst; Schlenk technique; regioselective reaction; | 47% |
Conditions | Yield |
---|---|
With air In water; acetonitrile for 1h; Solvent; Irradiation; | A 21.1% B 21.7% |
Benzoic acid 2-iodo-5-methoxy-phenyl ester
Benzophenone-3
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; diethyl ether; hexane at -70℃; for 2h; | 16% |
Conditions | Yield |
---|---|
With carbon disulfide; aluminium trichloride |
Benzophenone-3
Conditions | Yield |
---|---|
With sodium hydroxide |
benzoyl chloride
1,3-Dimethoxybenzene
A
Benzophenone-3
B
2,4-dimethoxybenzophenone
Conditions | Yield |
---|---|
With mercury dichloride |
Conditions | Yield |
---|---|
With methanol; sodium hydroxide |
3-(2-hydroxy-4-methoxyphenyl)-3-phenyl allyl alcohol
A
Benzophenone-3
B
(Z)-3-(2-Hydroxy-4-methoxy-phenyl)-3-phenyl-propenal
Conditions | Yield |
---|---|
With air; rose bengal In tetrachloromethane for 48h; Irradiation; |
benzoyl chloride
1,3-Dimethoxybenzene
A
Benzophenone-3
B
2,4-dimethoxybenzophenone
Conditions | Yield |
---|---|
at 100℃; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / PPA / 8 h / 90 °C 2: 90 percent / BeCl2 / toluene / 3 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / PPA / 8 h / 90 °C 2: 90 percent / BeCl2 / toluene / 3 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine 2: 16 percent / n-butyllithium / tetrahydrofuran; diethyl ether; hexane / 2 h / -70 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: (COCl)2, DMF / tetrahydrofuran 2: pyridine 3: 16 percent / n-butyllithium / tetrahydrofuran; diethyl ether; hexane / 2 h / -70 °C View Scheme | |
Multi-step reaction with 2 steps 1: iodine; carbon monoxide / 1,2-dichloro-ethane / 24 h / 20 °C / 3040.2 Torr / Sealed tube 2: 22 h / 100 °C / Glovebox View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous ethanol / und Eintragen des Reaktionsgemisches in heisses Wasser 2: aq. NaOH solution; methanol View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous ethanol / und Eintragen des Reaktionsgemisches in heisses Wasser 2: aq. NaOH solution; methanol View Scheme |
Benzophenone-3
methylamine
5-methoxy-2-[(methylimino)(phenyl)methyl]phenol
Conditions | Yield |
---|---|
at 20℃; for 23h; Neat (no solvent); | 100% |
Benzophenone-3
allylmagnesium bromide
2-(1-hydroxy-1-phenylbut-3-enyl)-5-methoxyphenol
Conditions | Yield |
---|---|
Stage #1: Benzophenone-3; allylmagnesium bromide In tetrahydrofuran at 0 - 20℃; Grignard reaction; Inert atmosphere; Stage #2: With water In tetrahydrofuran at 0℃; for 0.0833333h; | 100% |
Benzophenone-3
2,2,6-trimethyl-4H-1,3-dioxin-4-one
3-acetyl-7-methoxy-4-phenylcoumarin
Conditions | Yield |
---|---|
In decalin for 12h; Solvent; Reflux; | 100% |
Conditions | Yield |
---|---|
With sulfur trioxide; acetic acid In 1,2-dichloro-ethane at 25℃; for 3h; Inert atmosphere; | 98.82% |
With chlorosulfonic acid In ethyl acetate at 45℃; Temperature; | 96% |
With chlorosulfonic acid In phthalic acid dimethyl ester | |
With chlorosulfonic acid at 25℃; for 20h; Inert atmosphere; Autoclave; |
1-(chloromethyl)-1H-benzotriazole
Benzophenone-3
[2-(1-benzotriazol-1-ylmethoxy)-4-methoxyphenyl](phenyl)methanone
Conditions | Yield |
---|---|
Stage #1: Benzophenone-3 With sodium hydroxide In ethanol at 20℃; for 5h; Stage #2: 1-(chloromethyl)-1H-benzotriazole In N,N-dimethyl-formamide at 70℃; for 12h; Further stages.; | 98% |
Benzophenone-3
vinylmagnesium chloride
1-(2'-hydroxy-4'-methoxyphenyl)-1-phenylprop-2-en-1-ol
Conditions | Yield |
---|---|
In tetrahydrofuran at -78 - 20℃; for 0.5h; Inert atmosphere; | 98% |
Benzophenone-3
allyl bromide
(2-(allyloxy)-4-methoxyphenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With potassium carbonate | 97% |
With potassium carbonate In acetone at 50℃; | 80% |
Benzophenone-3
1-(benzotriazol-1-yl)-1-chloroethane
[2-(1-benzotriazol-1-ylethoxy)-4-methoxyphenyl](phenyl)methanone
Conditions | Yield |
---|---|
Stage #1: Benzophenone-3 With sodium hydroxide In ethanol at 20℃; for 5h; Stage #2: 1-(benzotriazol-1-yl)-1-chloroethane In N,N-dimethyl-formamide at 70℃; for 12h; Further stages.; | 97% |
Benzophenone-3
Methyltriphenylphosphonium bromide
5-methoxy-2-(1-phenylethenyl)phenol
Conditions | Yield |
---|---|
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: Benzophenone-3 In tetrahydrofuran at 0 - 60℃; for 12.5h; Inert atmosphere; | 96% |
Stage #1: Methyltriphenylphosphonium bromide With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: Benzophenone-3 In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere; Schlenk technique; |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 3h; Cooling with ice; | 96% |
Benzophenone-3
2-[imino(phenyl)methyl]-5-methoxyphenol
Conditions | Yield |
---|---|
With ammonia In methanol at 20℃; Sealed tube; | 94% |
With ammonia In methanol at 20℃; for 2h; Inert atmosphere; |
Conditions | Yield |
---|---|
at 120℃; for 0.166667h; Schlenk technique; | 94% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 3h; Cooling with ice; | 94% |
2-bromophenylacetic acid
Benzophenone-3
(2-benzoyl-5-methoxyphenoxy)phenylacetic acid
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran Heating; | 93% |
Benzophenone-3
cyanoacetic acid
7-methoxy-2-oxo-4-phenyl-2H-chromene-3-carbonitrile
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In acetic acid butyl ester; ethyl acetate at 120℃; Perkin condensation; | 93% |
Benzophenone-3
4-[(4-chloro-2-pyrimidinyl)amino]benzonitrile
4-{4-[2-benzoyl-5-methoxyphenoxy]pyrimidin-2-ylamino}benzonitrile
Conditions | Yield |
---|---|
Stage #1: Benzophenone-3 With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 4-[(4-chloro-2-pyrimidinyl)amino]benzonitrile In N,N-dimethyl-formamide at 80℃; Inert atmosphere; | 92.9% |
Benzophenone-3
ethyl bromoacetate
(2-Benzoyl-5-methoxy-phenoxy)-acetic acid ethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 96h; Heating; | 92% |
With sodium hydride 1.) DMF, 1 h, 2.) DMF, 70 deg C, 16 h; Multistep reaction; |
Conditions | Yield |
---|---|
In isopropyl alcohol for 6h; Heating; | 92% |
Conditions | Yield |
---|---|
In ethanol at 20℃; for 5h; | 92% |
Conditions | Yield |
---|---|
In methanol for 6h; Reflux; | 92% |
In methanol; ethanol for 12h; Reflux; |
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; for 6h; chemoselective reaction; | 92% |
styrene
Benzophenone-3
Conditions | Yield |
---|---|
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate In 1,2-dichloro-ethane at 60℃; for 12h; Green chemistry; | 92% |
Conditions | Yield |
---|---|
In ethanol at 20℃; for 2h; | 91% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 3h; Cooling with ice; | 91% |
Conditions | Yield |
---|---|
In water; acetonitrile at 20℃; for 2h; Electrochemical reaction; | 91% |
2-methyl-3-bromo-1-propene
Benzophenone-3
[4-Methoxy-2-(2-methyl-allyloxy)-phenyl]-phenyl-methanone
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 2h; Inert atmosphere; Reflux; | 90% |
With potassium carbonate | 85% |
1.Introduction of Oxybenzone
Oxybenzone, with its CAS NO 131-57-7, is a kind of white or light yellow crystalline powder. It has synonyms of Ultraviolet absorbent UV-9;2-Hydroxy-4-methoxy benzophenone(UV9);Uvinul 9;Sunscreen UV-15;UV 9;2-Hydroxy-4-methoxybenzophenone;Methanone,(2-hydroxy-4-methoxyphenyl)- phenyl- and Benzophenone, 2-hydroxy-4-methoxy-. Oxybenzone should be stored in shady and cool warehouse and mainly used as cosmetic raw materials.
2.Structure descriptors of Oxybenzone
IUPAC Name: (2-hydroxy-4-methoxyphenyl)-phenylmethanone
InChI: InChI=1S/C14H12O3/c1-17-11-7-8-12(13(15)9-11)14(16)10-5-3-2-4-6-10/h2-9,
15H,1H3
InChIKey: DXGLGDHPHMLXJC-UHFFFAOYSA-N
Canonical SMILES : COC1=CC(=C(C=C1)C(=O)C2=CC=CC=C2)O
3.Biomedical effects of Oxybenzone
Oxybenzone is a commonly used, chemical UV-absorber. It has been used for many years to protect against UV-radiation. Previous studies have shown that BZ-3 penetrates the skin, and it can be found in urine, feces, and blood. In this study /the authors/ examined the percutaneous absorption of BZ-3. The amount of BZ-3 absorbed was measured in urine, as experimental studies in the rat have shown that urine is the major route of excretion. Eleven volunteers applied the recommended amount of a commercially available sunscreen and urine samples were collected during a 48-hr period after application. The average total amount excreted was 11 mg, median 9.8 mg, which is approximately 0.4% of the applied amount of BZ-3. Some of the volunteers still excreted BZ-3 48 hr after application. It is evident that BZ-3 undergoes conjugation in the body to make it water soluble. However, we do not know at what age the ability to conjugate is fully developed, and therefore for children physical filters such as titanium dioxide and/or zinc oxide might still be considered a more appropriate sunscreen component.
4.Toxicity data of oxybenzone
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Source |
mouse | LD50 | intraperitoneal | 300mg/kg (300mg/kg) | National Technical Information Service. Vol. AD277-689, |
rat | LD50 | oral | 7400mg/kg (7400mg/kg) | Journal of the American College of Toxicology. Vol. 2(5), Pg. 35, 1983. |
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