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CAS No. : | 131-53-3 | MDL No. : | MFCD00002218 |
Formula : | C14H12O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MEZZCSHVIGVWFI-UHFFFAOYSA-N |
M.W : | 244.24 g/mol | Pubchem ID : | 8569 |
Synonyms : |
1. Dioxybenzone |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine hydrochloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aluminium trichloride; chlorobenzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With pyridine hydrochloride at 210 - 215℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
d. Triol, Me2SO4, in wss Alkali; | ||
As examples of the benzophenone-type ultraviolet absorber, the following can be mentioned but should not be considered limiting: 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octyloxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, bis(5-benzoyl-4-hydroxy-2-methoxyphenyl)methane, 2,2',4,4'-tetrahydroxybenzophenone, | ||
The preferred compounds to which the invention is applicable, but not limited, include the following: 2,4-dihydroxybenzophenone 2,2',4-trihydroxybenzophenone 2,2'4,4'-tetrahydroxybenzophenone 2,2'-dihydroxy-4-methoxybenzophenone 2,2'-dihydroxy-4,4'-dimethoxybenzophenone 2-hydroxy-4-methoxybenzophenone 2-hydroxy-4-octyloxybenzophenone 2-hydroxy-4-dodecyloxybenzophenone. |
Examples of the ultraviolet absorber include the following: 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octoxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, bis(5-benzoyl-4-hydroxy-2-methoxyphenyl)methane, 2,2',4,4'-tetrahydroxybenzophenone, 2-(2-hydroxy-5-methylphenyl)benzotriazole, 2-[2-hydroxy-3-(3,4,5,6-tetrahydrophthalimidemethyl)-5-methylphenyl]benzotriazole, 2-(3-t-butyl-2-hydroxy-5-methylphenyl)-5-chlorobenzotriazole, 2-(2-hydroxy-5-t-octylphenyl)benzotriazole, ... | ||
The following benzophenones: 2,4-Dihydroxybenzophenone 2,2'-Dihydroxy-4-methoxybenzophenone 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone | ||
X2 and Z3 are different from Y and cannot simultaneously assume the meaning Z1 or Z2 or Z3; and a benzphenone selected from the group consisting of ... 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2,2',4,4'-tetrahydroxybenzophenone, 2,4-dihydroxybenzophenone, and 2,2'-dihydroxy-4-methoxybenzophenone, | ||
Illustrative examples of the above described benzophenones are listed below. 2-Hydroxy-4-methoxybenzophenone, 2,2'-Dihydroxy-4-methoxybenzophenone, 2-Hydroxy-4-methoxy-2'-carboxybenzophenone, 2,2-dihydroxy-4-n-octoxybenzophenone, 2-hydroxy-4-n-octoxybenzophenone, 5-chloro-2-hydroxybenzophenone, 2,4-dihydroxybenzophenone, 4-dodecycloxy-2-hydroxybenzophenone, 2-hydroxy-4-decyloxybenzophenone, ... | ||
Specific examples of bisphenols include: ... bis(4-hydroxy-2-nitrophenyl)sulfone; 4,4'-dihydroxybenzophenone; 2,2'-dihydroxy-4-methoxybenzophenone; 4,4'-dihydroxydiphenyl ether; ... | ||
Broadband filters which are preferably combined with one or more compounds of formula (I) in a preparation according to the present invention are selected from the group consisting of ● 2-ethylhexyl-2-cyano-3,3-diphenyl acrylate (Neo Heliopan303)● ethyl-2-cyano-3,3'-diphenyl acrylate● 2-hydroxy-4-methoxybenzophenone (Neo HeliopanBB)● 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid● dihydroxy-4-methoxybenzophenone● 2,4-dihydroxybenzophenone● tetrahydroxybenzophenone● 2,2'-dihydroxy-4,4'-dimethoxybenzophenone● 2-hydroxy-4-n-octoxybenzophenone... | ||
Broadband filters which are preferably combined with one or more compounds of formula (I) in a preparation according to the present invention are selected from the group consisting of 2-ethylhexyl-2-cyano-3,3-diphenyl acrylate (Neo Heliopan303)ethyl-2-cyano-3,3'-diphenyl acrylate2-hydroxy-4-methoxybenzophenone (Neo HeliopanBB)2-hydroxy-4-methoxybenzophenone-5-sulfonic aciddihydroxy-4-methoxybenzophenone2,4-dihydroxybenzophenonetetrahydroxybenzophenone2,2'-dihydroxy-4,4'-dimethoxybenzophenone2-hydroxy-4-n-octoxybenzophenone... | ||
Ultraviolet absorbers are illustrated below, but the embodiments of the present invention are not limited to these compounds: benzophenone-based ultraviolet absorbers such as 2,4-dihydroxybenzophenone,...bis-(2-methoxy-4-hydroxy-5-benzoylphenyl)methane,2-(2'-hydroxy-3',5'-di-t-amylphenyl)-benzophenone,2-hydroxy-4-dodecyloxybenzophenone,2-hydroxy-4-octadecyloxybenzophenone,2,2'-dihydroxy-4-methoxybenzophenone, and2-hydroxy-4-benzyloxybenzophenone;para-t-butylphenyl salicylate,paraoctylphenyl salicylate,... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 69 percent / Py*HCl / 6 h / 210 - 215 °C 2: 86 percent / K2CO3 / acetone / 8 h / Heating 3: 1.) NaOH, 2.) HCl / 1.) EtOH, H2O, 25 deg C, 4 h, 2.) H2O, pH 3.5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 69 percent / Py*HCl / 6 h / 210 - 215 °C 2: 86 percent / K2CO3 / acetone / 8 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 69 percent / Py*HCl / 6 h / 210 - 215 °C 2: 86 percent / K2CO3 / acetone / 8 h / Heating 3: 1.) NaOH, 2.) HCl / 1.) EtOH, H2O, 25 deg C, 4 h, 2.) H2O, pH 3.5. 4: 1.) NaBH4, NaOH, 2.) NaHCO3 / 1.) H2O, 50-55 deg C, 3 h, pH 8.0-8.5, 2.) 10 deg C, 1 h. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 69 percent / Py*HCl / 6 h / 210 - 215 °C 2: 86 percent / K2CO3 / acetone / 8 h / Heating 3: 1.) NaOH, 2.) HCl / 1.) EtOH, H2O, 25 deg C, 4 h, 2.) H2O, pH 3.5. 4: 1.) NaOH, Zn, 2.) TFA / 1.) aq. EtOH, reflux, 6 h, 2.) 1,2-dimethoxyethane, 25 deg C, 4 h. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 2: pyridine hydrochloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 2: pyridine hydrochloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium iodide; potassium carbonate In water; ethyl acetate; isopropyl alcohol | 22 Preparation of Methyl 3-Methoxy-12H-dibenzo[d,g][1,3]dioxocin-12-one-6-carboxylate Example 22 Preparation of Methyl 3-Methoxy-12H-dibenzo[d,g][1,3]dioxocin-12-one-6-carboxylate (2-Hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)methanone (16.1 g, 65.9 mmol), 36.5 g (258 mmol) of potassium carbonate, and 3.00 g (18 mmol) of potassium iodide were suspended in 250 ml of 2-propanol and heated with stirring. Dichloroacetic acid (6.00 ml, 72.6 mmol) was added slowly with a syringe and the mixture heated at reflux with stirring. After 48 hours another 5.00 ml of dichloroacetic acid was added and the reaction continued for another 48 hours. The mixture was then allowed to cool and was concentrated by evaporation under reduced pressure to obtain a solid residue. The residue was dissolved in 500 ml of water and the solution extracted with 200 ml of ether. The aqueous layer was then acidified with concentrated aqueous hydrochloric acid and then extracted twice with 500 ml portions of ether and once with 300 ml of ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain 3-methoxy- 12H-dibenzo[d,g][1,3]dioxocin-12-one-6-carboxylic acid as a semi-solid residue. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium diacetate; dipotassium peroxodisulfate / 4 h / 50 °C 2: silica gel / hexane; dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With silica gel In hexane; dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With dipotassium peroxodisulfate; palladium diacetate; trifluoroacetic acid; trifluoroacetic anhydride at 25 - 30℃; for 48h; regioselective reaction; | |
82% | With dipotassium peroxodisulfate; palladium diacetate; trifluoroacetic acid; trifluoroacetic anhydride at 20℃; regioselective reaction; | |
51% | With dipotassium peroxodisulfate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; trifluoroacetic acid; trifluoroacetic anhydride at 80℃; for 20h; Sealed tube; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With hydrogen bromide; acetic acid at 110℃; | 2.2 synthesis of 2, 2'-dihydroxy-4-methoxybenzophenone Weighed 60 mL of glacial acetic acid and hydrobromic acid (48%) and 2, 2 ', 4-trimethoxybenzophenone(0.18 mol) in a three-necked flask, the reaction temperature was controlled at 110 ° C for 5 to 6 hours,The reaction mixture was cooled and washed with water to remove the acidic substance. The mixture was separated and extracted with ethyl acetate. After drying, the ethyl acetate was removed by evaporation to give an oily substance, which was recrystallized from 150 ml of n-hexane as a solvent and the temperature was controlled at 0 to 5 ° C Crystallization, filtration, drying under reduced pressure to get pale yellow crystalline powder 2, 2 '-dihydroxy-4-methoxybenzophenone 37. 3g.The yield was 85%, mp 67 ~ 69 ° C, and the content was 99.0% by HPLC. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74.43% | With sulfolane; sodium carbonate; zinc(II) chloride In toluene at 45℃; for 2h; | 2 Example 2 Weighing 250 g sulfolane, 100 ml phosphorus oxychloride, 150 g (0.2 µM) anhydrous zinc chloride, adding with stirring 1000 ml in the reaction bottle, heated to 55 °C reaction 1 hours, then adding salicylic acid 72.5 g (0.53 µM), resorcinol 55.0 g (0.5 µM), heated to 72 °C reaction 2 hours, after the reaction cooling the dripping water 50 ml the termination of the reaction, the reaction solution is poured into 1000 ml of ice water reaction mixing and 10 hours, cooling crystallization, at room temperature the product is collected after filtering, drying after heavy 108.3 g, GC detection 2, 2', 4 - trihydroxy benzophenone content 95.20%, yield is 94.17%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With boron tribromide In dichloromethane at -78 - 20℃; | 5.1 To reaction flask charged with a suspension of (2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)methanone (24 g, 81.88 mmol) in 50 mL dichloromethane, was added BBr3 (50 g, 163.77 mmol) (50 g in 100 mL of dichloromethane) dropwise over a period of 30 min at -78° C. The resultant solution was slowly warmed to room temperature and stirring continued overnight. Saturated aqueous NaCl (150 mL) solution was carefully added to the reaction mixture while stirring. After phases were separated, the organic phase was retained and the aqueous layer was extracted with dichloromethane (2×200 mL). The organic extracts were combined, washed twice with brine (100 mL) and dried over anhydrous magnesium sulfate. After removal of the solids and evaporation of the solvent, the filtrate offered a product which was purified by combiflash on silica gel eluting with dichloromethane/ethyl acetate (EtOAc) (90/10, v/v). The product thus obtained was a light yellow solid, used directly for the next step. NMR showed that the product had a structure consistent with (2,4-dihydroxyphenyl)(2-hydroxyphenyl)methanone. | |
With boron tribromide In dichloromethane for 48h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dimethyl sulfoxide at 20℃; for 12h; | 1.1 1) Preparation of second monomer (UV blocking monomer) using Dioxybenzone 1 g of dioxybenzone was dissolved in 10 ml of DMSO solution, 0.5 ml of methacryloyl chloride was added.The resulting precipitate was filtered through a reaction at room temperature for 12 hours,The precipitate was dried at room temperature for 24 hours or more, A second monomer, methacryloyl dioxybenzone, was prepared. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrahydrofuran / 3 h / 0 - 70 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; (5aR,10bS)-2-mesityl-5a,10b-dihydro-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate / dichloromethane / 36 h / 24 °C / Molecular sieve; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrahydrofuran / 3 h / 0 - 70 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; BF4(1-)*C21H22N3O(1+) / dichloromethane / 36 h / 24 °C / Molecular sieve; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In tetrahydrofuran at 0 - 70℃; for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium iodide; potassium carbonate / water; ethyl acetate; isopropyl alcohol 2: methanol; hexane 3: hydrogen; acetic acid / palladium / ethanol; hexane; water; ethyl acetate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium iodide; potassium carbonate / water; ethyl acetate; isopropyl alcohol 2: methanol; hexane 3: hydrogen; acetic acid / palladium / ethanol; hexane; water; ethyl acetate 4: sodium hydroxide / tetrahydrofuran; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium iodide; potassium carbonate / water; ethyl acetate; isopropyl alcohol 2: methanol; hexane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water; NADPH In aq. phosphate buffer at 37℃; for 2.5h; Microbiological reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | Stage #1: (2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone With sodium hydroxide In methanol Stage #2: mer-[(1,4-bis(diphenylphosphino)butane)aquatrichlororuthenium(III)] In methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With benzenesulfonic acid In para-xylene at 150℃; for 5h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform at 80℃; | 4 Preparation of epoxy resin curing agent D: Add 50 g of n-propanol into a 100 mL three-necked flask, and then add 0.02 mol of 2.2'-dihydroxy-4-methoxybenzophenone and 0.01 mol of ethylenediamine respectively.Put the three-neck flask on a magnetic stirrer with a jacket, connect the stirrer, water separator and condenser, turn on the stirrer to stir, control the reaction at 80°C for 0.5h, and discharge the material to obtain a solidified epoxy resin Agent D |