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CAS No. : | 937-41-7 | MDL No. : | MFCD00048145 |
Formula : | C9H8O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 148.16 g/mol | Pubchem ID : | 61242 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 42.27 |
TPSA : | 26.3 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.73 cm/s |
Log Po/w (iLOGP) : | 2.04 |
Log Po/w (XLOGP3) : | 2.08 |
Log Po/w (WLOGP) : | 1.78 |
Log Po/w (MLOGP) : | 2.16 |
Log Po/w (SILICOS-IT) : | 2.02 |
Consensus Log Po/w : | 2.02 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.27 |
Solubility : | 0.787 mg/ml ; 0.00531 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.26 |
Solubility : | 0.811 mg/ml ; 0.00547 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.51 |
Solubility : | 0.456 mg/ml ; 0.00308 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.47 |
Signal Word: | Danger | Class: | 9 |
Precautionary Statements: | P261-P273-P305+P351+P338 | UN#: | 3082 |
Hazard Statements: | H315-H319-H335-H411-H372 | Packing Group: | Ⅲ |
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 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With lithium hydroxide monohydrate; di-tert-butyl dicarbonate; magnesium sulfate; at 25℃; for 24h; | General procedure: In a 100 mL capacity eggplant-shaped flask, 10.000 grams (106.26 mmol) of 6 phenol, 7.657 grams (106.26 mmol) of 22 acrylic acid, 23.664 grams (106.26 mmol) of 8 di-t-butyl dicarbonate, 0.046 grams (0.53 mmol, 0.5 mol %) of 23 lithium bromide, and 0.064 grams (0.53 mmol, 0.5 mol %) of 24 magnesium sulfate were added successively. Then, reaction was carried out at 25 C. while the mixture was stirred. Accordingly, 25 phenyl acrylate was produced. The reaction result obtained 24 hours after the start of reaction is shown in Table 4. |
35% | With potassium carbonate; 2-chloropyridinium iodide; In dichloromethane; at 20℃; for 4h; | General procedure: To a suspension of 562 mg 2-chloropyridinium iodide (2.2 mmol, 1.1 equiv) and 612 mg potassium carbonate (4.4 mmol, 2.2 equiv) in 20 cm3 dichloromethane, the corresponding acid (2.2 mmol, 1.1 equiv) and the corresponding phenol (2.0 mmol, 1.0 equiv) were added. The reaction was stirred at room temperature for 4 h. Thereaction mixture was then filtered through a silica plug, washed with dichloromethane, and concentrated. The residue was purified by column chromatography to yield the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; at 20℃; for 24h;Inert atmosphere; | Example 1; Materials and Laboratory Synthesis of the Monomers of the Present Invention; The well plates and most chemicals used in the monomer syntheses and testing, including the alcoholic precursors, triethylamine (TEA), acryloyl chloride, well plates, and acetonitrile, were purchased from Sigma-Aldrich. The dichloromethane also used in the syntheses was purchased from Pharmacia. The material used for the coating formulations was obtained from Allied Photochemical and is a proprietary formulation. Cytec Specialty Chemicals provided HDODA used in the photo-DSC testing. Albemarle Corporation donated the initiator, 2,2-dimethoxy-2-acetophenone (DMPA) used in the photo-DSC studies. The uncoated, polished stainless steel plates were purchased from Q-Panel Products. Methyl ethyl ketone (MEK) for the double rub solvent resistance test was purchased from The Paint Center. Pap-smear cytology fixative spray was obtained from Andwin Scientific. The E. coli was stained using Hema-diff solution 3:thiazine dye from Anaphth.Each alcohol precursor was dissolved in dichloromethane after adding TEA in slight molar excess. Under a ventilation hood, acryloyl chloride was added dropwise producing hydrogen chloride gas, which was, inpart, consumed by the TEA. The round bottom flask was purged with nitrogen for five seconds and stoppered to provide a nitrogen atmosphere for the reaction to take place. The reaction mixture stirred for 24 hours at room temperature using a magnetic stir bar to allow for complete reaction. TEA?HCl precipitate formed which was removed by suction filtration. Unreacted acryloyl chloride was removed by washing with five milliliters (5 ml) of deionized water five times in a separatory funnel. A rotary evaporator was used to remove any excess dichloromethane. The reaction scheme is shown below (Reaction 1). The structure of each monomer was verified by infrared spectroscopy (IR) and nuclear magnetic resonance (NMR).Furthermore, it is recognized that the industrial synthesis would involve a synthetic scheme involving either: 1) the esterification reaction of acrylic acid with the alcoholic precursor, or 2) the transesterification reaction of methyl acrylate (or similar derivative) with the alcoholic precursor with both procedures requiring an acid catalyst, elevated temperatures, and a vacuum to remove the condensate from the reaction vessel. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With phosphorus pentachloride In neat (no solvent) 1.) 110-120 deg C, 1 h, 2.) room temp., 2.5 h then 90 deg C, 3 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aluminium trichloride In neat (no solvent) 1.) cooled by tap water, 16 h, 2.) 80 deg C, 4 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | ||
19.4 g | With aluminium trichloride In neat (no solvent) 1.) 80-90 deg C, 3 h, 2.) 100 deg C, 1 h; Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With aluminum (III) chloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: To a solution of phosphinothiourea 1b (0.02 mmol) in THF (1.0 mL) was added acrylate (0.4 mmol) at 0 C. After 10 min stirring at this temperature, isatin (0.2 mmol) was added. The reaction mixture was stirred at 0 C (monitoring by TLC). Then the resulting solution was concentrated under reduced pressure and the residue was purified by a flash column chromatography on silica gel to afford the desired adducts and the ee values were determined by HPLC analysis with chiral column. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: To a solution of phosphinothiourea 1b (0.02 mmol) in THF (1.0 mL) was added acrylate (0.4 mmol) at 0 C. After 10 min stirring at this temperature, isatin (0.2 mmol) was added. The reaction mixture was stirred at 0 C (monitoring by TLC). Then the resulting solution was concentrated under reduced pressure and the residue was purified by a flash column chromatography on silica gel to afford the desired adducts and the ee values were determined by HPLC analysis with chiral column. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With [Rh(OH)(cod)]2; In toluene; at 80℃; for 24h;Inert atmosphere; | To a solution of [Rh(OH)(cod)]2 (2.3 mg, 0.0050 mmol, 2 mol % of Rh) in toluene (0.5 mL) were added propargylic alcohol 1 (0.50 mmol) and acrylate ester 2 (1.50 mmol, 3 equiv), and the mixture was heated at 80 C for 24 h. The reaction mixture was passed through a pad of silica gel with Et2O, and it was concentrated on a rotary evaporator. The residue was subjected to preparative TLC (silica gel) or flash column chromatography (silica gel) with hexane/ethyl acetate to give product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28%; 47% | With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20℃; for 24h; | General procedure: 1 (0.5 mmol), alpha, beta-unsaturated carbonyl 2 (1.0 mmol) and DBU (0.1 mmol) were dissolved in CH2Cl2 (2 mL), and then the reaction mixture was stirred at room temperature. After the reaction was completed, the mixture was directly charged onto silica gel and purified through flash chromatography to furnish the corresponding product 3 and 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27%; 48% | With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20℃; for 24h; | General procedure: 1 (0.5 mmol), alpha, beta-unsaturated carbonyl 2 (1.0 mmol) and DBU (0.1 mmol) were dissolved in CH2Cl2 (2 mL), and then the reaction mixture was stirred at room temperature. After the reaction was completed, the mixture was directly charged onto silica gel and purified through flash chromatography to furnish the corresponding product 3 and 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With C8H20N2O2Pd*2C2H4O2; In N,N-dimethyl-formamide; at 50℃; for 3h; | General procedure: Under air atmosphere, a mixture of olefin (0.5 mmol), arylboronic acid (1.0 mmol), alkoxopalladium complex (4 mg, 2 mol %), oxidant (1.0 mmol) and DMF (1.5 mL) was stirred at 50 C for 3 h. The reaction mixture was cooled to room temperature, and then directly purified by preparative thin layer chromatography on silica gel using petroleum ether/ethyl acetate as an eluent to give desired compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With pyridine; copper dichloride; In 1,4-dioxane; at 100℃; for 1h;Inert atmosphere; Schlenk technique; | General procedure: CuCl2 (7 mg, 10 mol%), alkene (0.5 mmol), 1,4-dioxane (2 mL), CF3SO2Cl (152 mg, 1.8 eq.) and pyridine (4 mg, 10 mol%) were added into a Schlenk tube under a N2 atmosphere. The reaction mixture was stirred at 100 C for 1 h. After being cooled to room temperature, the solid was removed by filtration and washed with DCM (30 mL). The combined organic solution was evaporated, and the resulting crude product was purified by flash column chromatography to give the products 3 or 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With 1,4-diaza-bicyclo[2.2.2]octane; In 1,4-dioxane; dichloromethane; at 20℃; for 40h; | N- trifluoromethylthio-4-nitro phthalimide (65.7mg, 0.225mmol), 1- acrylate, phenyl (22.2mg, 0.15mmol), DABCO (8.75mg, 0.075mmol) and di a mixed solution of methylene chloride and 1,4-dioxane: mixture (volume ratio 1 1,0.45mL) was stirred at room temperature for 40 hours.Concentrated under reduced pressure, by column chromatography to give product 1- (4-nitro-phthalimide) -2-trifluoromethylthio - phenyl propionate, 80% isolated yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With [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; In methanol; at 20 - 25℃; for 24h;Irradiation; Schlenk technique; Inert atmosphere; | The unreacted olefin I-15 was added to a 10 mL Schlenk tube(R1 = phenolic ester, R2 = hydrogen, n = 0) (37.0 mg, 0.25 mmol)Sodium trifluoromethanesulfinate(78.0 mg, 0.50 mmol) and Ir [dF (CF3) ppy] 2 (dtbbpy) PF6 (5.6 mg, 0.005 mmol).After evacuation of argon, 3 mL of solvent (methanol) was added, and the reaction was carried out by stirring the fluorescent lamp with a Schuling tube.Fluorescent wavelength range of visible light, power 36W, the reaction temperature is room temperature, the reaction time is 24 hours.After completion of the reaction, the reaction was quenched by adding water to the system and extracting with ethyl acetate (3 x 10 mL). The organic phase was separated, dried over anhydrous Na2SO4, filtered and the solvent was removed by rotary evaporation.The residue was purified by column chromatography on ethyl acetate / petroleum ether = 1: 20 to give the desired product II-1532 mg in 58% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52%Spectr. | With C25H42MnNO2P2; In neat (no solvent); at 20℃; for 26h; | A stock solution containing 5 mg / mL (O.Olmmol / mL) of c-[Mn(PNP*tBu)(CO)2] (2) in the particular reaction media (solvent: C6,THF, DCM, or -pentane) was prepared. To 0.5 mL of the stock solution (0.005 mmol catalyst) 1 mmol of nitrile is added followed by the addition of 1 mmol of the specific alpha,beta-unsaturated compound. The mixture stirred at room temperature (-22 C) for the indicated time and quenched by introduction of non-dried -pentane. The yield was determined by integration of lH NMR signals with respect to the suitable standard either toluene for the reaction in THF, dichloromethane, and -pentane, or dioxane for C6 (done before quenching). The products were purified according to the indicated method, isolated yields are reported. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With bis-triphenylphosphine-palladium(II) chloride; triethylamine; In dimethyl sulfoxide; at 100℃; for 15h;Inert atmosphere; | General procedure: A solution of aryl bromide (1mmol, 1equiv), acrylate (2equiv), PdCl2(PPh3)2 (5mol%) and Et3N (5equiv) in DMSO (2mL) under argon was heated at 100C for 15h. Water (10mL) was then added followed by sodium chloride (until saturation) and the reaction mixture was extracted with ethyl acetate (3×15mL). The organic layers were combined and washed with brine, dried over MgSO4, filtered and the solvent was removed under reduced pressure. The residue was purified on a column of silica gel to afford the desired pure coupling product. 4.2.6 (E)-3-(2-Formylphenyl)<strong>[937-41-7]acrylic acid phenyl ester</strong> 11e General Heck procedure using 2-bromobenzaldehyde 16 (185 mg, 1 mmol, 2 equiv) and <strong>[937-41-7]phenyl acrylate</strong> 19e (296 mg, 2 mmol, 2 equiv) affords 11e (86 mg, 0.34 mmol, yield = 34%) as a colorless oil. 1H NMR (300 MHz, CDCl3): delta = 10.20 (s, 1H), 8.65 (d, J = 15.9 Hz, 1H), 7.83-7.72 (m, 1H), 7.65-7.46 (m, 3H), 7.36-7.26 (m, 2H), 7.19-7.06 (m, 3H), 6.48 (d, J = 15.9 Hz, 1H); 13C NMR (75 MHz, CDCl3): delta = 191.8, 164.6, 150.8, 143.1, 136.2, 134.0 (2 signals), 132.8, 130.3, 129.5 (2C), 128.1, 125.9 (2C), 122.2, 121.6; HRMS (ESI+) m/z calcd for C16H13O3 [MH]+ 253.08592, found 253.08644. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | To 50mL three-necked flask, Bis (fluoren-9-yl) methane(Compound 1) 1.00 g (2.9 mmol), tetrabutylammonium bromide 93 mg (0.29 mmol), 5mL THF were added & under a nitrogen atmosphere, it was stirred at roomtemperature. 50wt / wt% sodium hydroxide aqueous solution 0.40 mL was added andstirred for 15 minutes and then cooled to 3 C in an ice bath. Herein, <strong>[937-41-7]phenylacrylate</strong> 0.945 g (6.38 mmol) was added dropwise over 3 minutes, then agedsubsequently for 2 hours. This reaction solution was neutralized with 3Nhydrochloric acid and the desired compound was extracted with ethyl acetate20mL, then the aqueous and organic phases were separated. Bis [9- (2-phenoxycarbonyl ethyl) fluoren-9-yl] methane (Compound 2) in the organic phasewas determined by HPLC (44% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With dmap; oxygen; phenol; at 130 - 140℃; for 9h; | Example 28 In a 50 mL three-neck glass flask equipped with an air inlet, added were 6.5 grams (90 mmol) of acrylic acid, 16.0 grams (75 mmol) of diphenyl carbonate, 0.5 grams (4 mmol) of 4-dimethylaminopyridine as a catalyst, 0.004 grams of phenol as a polymerization inhibitor, and 1.3 grams (7 mmol) of diphenyl ether as an internal standard substance. While air was being blown into the mixture at a rate of 10 mL/min, the mixture was heated to an internal temperature of 130 C. and stirred for 6 hours. Then the mixture was heated to an internal temperature of 140 C. and stirred for 3 hours. As a result, the amount of produced phenyl acrylate was 6.5 grams (44 mmol). The yield of phenyl acrylate relative to diphenyl carbonate was 59%. From the example above, it is found that phenyl ester is obtained efficiently even when the material is changed from methacrylic acid to acrylic acid. |
49% | With magnesium monohydroxide; phenol; at 135℃; for 12h; | Three-necked glass flask equipped with an air inlet tube of 50mL,Acrylic acid 12.1g (168mmol), diphenyl carbonate, 12.0g (56mmol), as a catalyst, from the magnesium hydroxide 0.34g (6mmol), a phenol 0.01g, internal standard as a polymerization inhibitor in diphenylWere placed 0.95g (5mmol). While blowing the air at a flow rate of 10mL per minute to the mixed solution, the internal temperature is stirred for 12 hours, heated to 135 haetdayi result, the resulting phenyl-acrylate was 4.1g (28mmol). The yield of the diphenyl carbonate to phenyl acrylate was 49% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With dipotassium peroxodisulfate; tetrakis(triphenylphosphine) palladium(0); In acetonitrile; at 50℃; for 10h;Sealed tube; | To the screw-in test tube was added 0.25 mmol of phenyl-p-tolyl propynyl ether,0.35 mmol of <strong>[937-41-7]phenyl acrylate</strong>, 0.050 mmol of tetrakistriphenylphosphine palladium,0.50 mmol potassium persulfate, 2 ml acetonitrile,After the reaction was stirred at 50 C for 10 hours, heating and stirring were stopped, and the mixture was cooled to room temperature. The reaction material was evaporated under reduced pressure to remove the solvent, and then purified by column chromatography.To give 2-H-benzopyran derivatives,The column chromatography eluent used was a mixture of petroleum ether and ethyl acetate in a volume ratio of 25: 1,Yield 86%. |
Tags: 937-41-7 synthesis path| 937-41-7 SDS| 937-41-7 COA| 937-41-7 purity| 937-41-7 application| 937-41-7 NMR| 937-41-7 COA| 937-41-7 structure
[ 73839-82-4 ]
Di(naphthalen-(Z)-2-yl) maleate
Similarity: 0.87
[ 1092853-38-7 ]
3-(4-Hydroxyphenoxy)propyl acrylate
Similarity: 0.85
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P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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