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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
2'-Hydroxyacetophenone is a flavoring agent.
Synonyms: o-Hydroxyacetophenone; o-Acetylphenol
4.5
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Batch number can be found on the product's label following the word 'Batch'.
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Search for reports by entering the product batch number.
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CAS No. : | 118-93-4 |
Formula : | C8H8O2 |
M.W : | 136.15 |
SMILES Code : | C1=CC=CC(=C1O)C(=O)C |
Synonyms : |
o-Hydroxyacetophenone; o-Acetylphenol
|
MDL No. : | MFCD00002219 |
InChI Key : | JECYUBVRTQDVAT-UHFFFAOYSA-N |
Pubchem ID : | 8375 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
25% | With N-Bromosuccinimide; diisopropylamine; In carbon disulfide; at 0 - 20℃; | N-Bromosuccinimide (5.25 g, 29.5 mmol) was added at 0° C. to a mixture of 1-(2-hydroxyphenyl)ethanone (4.00 g, 29.5 mmol) and diisopropylamine (0.42 mL, 2.95 mmol) in carbon disulfide (50 mL), and the mixture was stirred for 1 hour at room temperature. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated sodium bicarbonate aqueous solution and water, then dried over magnesium sulfate, filtered, and concentrated at reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate-hexane 0:10-->2:8) to give 1.60 g of the titled compound (yield 25percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | Method 1 Preparation of 3,4-Dihydro-spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one hydrochloride A solution of 2-acetylphenol (5 g, 0.037 mmol), 1-benzoyl-4-piperidone (7.5 g, 0.037 mmol), pyrrolidine (2.6 g, 0.037 mol) and CH3 OH (50 ml) was heated at reflux for 8 hours. After cooling to room temperature overnight, the solid was filtered to yield 8.2 g of 1'-benzoyl-3,4-dihydro-spiro[(2H)-1-benzopyran-2,4'-piperidin]-4-one. The mother liquor was concentrated to dryness and the residue triturated with ether to yield an additional 1.7 g (83percent total yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.7% | In methanol; | 1'-Benzoylspiro[chroman-2,4'-piperidin]-4-one (7) A solution of 2'-hydroxyacetophenone (5, 5.88 mL, 48.85 mmol), 1-benzoyl-4-piperidone (6, 10 g, 49 mmol), and pyrrolidine (4.1 mL, 49 mmol) in 55 mL of methanol was heated in an oil bath at 65° C. After ~18 hours the oil bath was removed and the solution was allowed to cool to room temperature. Additional 1-benzoyl-4-piperidone (6, 100 mg, 0.5 mmol) was added and heating at 65° C. was resumed. After an additional ~2.5 hours the oil bath was removed and the solution was allowed to cool to room temperature. This mixture was concentrated under reduced pressure on a rotary evaporator followed by high vacuum to give a viscous, orange oil. This oil was triturated with diethyl ether to provide a solid that was collected by vacuum filtration, washed with diethyl ether, and dried in vacuo at room temperature to afford 1'-benzoylspiro[chroman-2,4'-piperidin]-4-one (7) as an off-white solid (14.72 g, 93.8percent yield). The filtrate was evaporated to dryness, triturated with diethyl ether, filtered, washed with diethyl ether, and dried in vacuo at room temperature to afford additional compound 7 as a pale tan solid (0.54 g, 3.7percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26%; 61% | With Oxone; ammonium bromide; In methanol; at 20℃; for 4.5h; | General procedure: Oxone (1.352 g, 2.2 mmol) was added to the well stirred solution of substrate (2 mmol) and NH4Br (0.215 g, 2.2 mmol) in methanol (10 ml) and the reaction mixture was allowed to stir at room temperature (or reflux temperature). After completion of the reaction, as monitored by TLC, the reaction mixture was quenched with aqueous sodium thiosulfate, and extracted with ethyl acetate (3×25 ml). Finally, the combined organic layer was washed with water, dried over anhydrous sodium sulfate, filtered and removal of solvent in vacuo yielded a crude residue, which was further purified by column chromatography over silica gel (finer than 200 mesh) to afford pure products. All the products were identified on the basis of 1H NMR and mass spectral data. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52%Chromat.; 6%Chromat.; 19%Chromat. | With N-Bromosuccinimide; In acetonitrile; at 20℃; for 2h; | General procedure: Reaction conditions: Thiourea (5.1 molpercent, 2 mg, 0.026 mmol) was added to an acetonitrile solution (10 mL) containing NBS (1.15 equiv, 104.4 mg, 0.587 mmol). Anisole (56.3 mg, 0.51 mmol) was added immediately to the resulting stirred solution and allowed to stir at room temperature for 10 min. The reaction was quenched by the addition of 10percent aqueous solution of Na2S2O3 (10 mL) and extracted with ethyl acetate (70 mL). The organic solution was then washed with additional 10percent Na2S2O3 (2 * 10 mL), followed by deionized water (3 * 15 mL) and brine (2 * 10 mL). The organic solution was then dried over anhydrous Na2SO4 and the solvent was evaporated in vacuo. The major product of each reaction was isolated by centrifugal thin-layer chromatography using a 2 mm thick silica gel 60GF254 coated plate (5percent CH2Cl2/hexanes). The products reported herein are known compounds and were characterised by GC-MS, IR, 1H and 13C NMR. Their spectroscopic data are in agreement with those reported in the literature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68.3% | In ethanol;Reflux; | General procedure: solutionof acid hydrazide (0.01 mol) and appropriate benzaldehyde/acetophenone (0.01 mol) in ethanol was refluxed for 5-6 h. The precipitated title compounds were then filtered off, washed with water and recrystallized from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | The 30 mmol of 4-(di-p-tolylamino)benzaldehyde and 30 mmol of 1-(2-hydroxyphenyl)ethanone were dissolved in 50 mL ethanol, and then the aqueous KOH solutions (60 mmol in 50 mL water) were dropwisely added into the reaction solution. The reaction was stirred for 24 h at room temperature. The mixture was neutralized with 1 M HCl, and the precipitation was collected and dried. The collected solid powder was then dissolved in 30 mL methanol, which was subsequently added with 10 mL water containing 30 mmol KOH. 20 mL of 30percent H2O2 solution was slowly added into the reaction solution in an ice-water bath. The resulting mixture was stirred at room temperature for overnight. After neutralization with HCl, the solid precipitate was collected, dried, and eventually recrystallized from ethanol. Yield = 59percent. 1H NMR (DMSO-d6, 500 MHz): delta = 9.38 (s, -OH), 8.10 (dd, 1H, J1 = 7.0 Hz, J2 = 1.0 Hz), 8.09 (d, 2H, J = 7.5 Hz), 7.79 (t, 1H), 7.71 (d, 1H, J = 7.0 Hz), 7.47 (t, 1H), 7.18 (d, 4H, J = 7.0 Hz), 7.03 (d, 4H, J = 7.0 Hz), 6.97 (d, 2H, J = 7.0 Hz), 2.30 (s, 6H). 13C NMR (DMSO-d6, 125 MHz): 172.43, 154.44, 149.05, 145.83, 143.88, 138.14, 133.60, 133.47, 130.34, 128.95, 125.42, 124.76, 124.50, 122.98, 121.45, 119.43, 118.28, 20.54. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Two equivalent molar amount of R-acetophenone [where R H(1 & 3) and ortho-OH (2 & 4)] was added into 100 mL beaker andwas dissolved in 20 mL of ethanol. 10 mL of 10% aqueous KOH waspoured gently into the beaker containing R-acetophenone and themixture was stirred for about 10 min 1,4-terephthaldehyde (0.67 g,0.0050 mol) and 2,5-dimethoxy-1,4-terephthaldehyde (0.20 g,0.0010 mol) were added into beaker (1 & 3) and (2 & 4), respectively.The mixture was stirred vigorously under room temperaturefor 4 h. After that, 3 M HCl was added until the solution wasneutralized. The obtained precipitate was filtered, rinsed withdistilled water and ethanol. The washed precipitate was allowed toair dried. Finally, the precipitate was purified via slow evaporationby using THF. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In sodium hydroxide; | (a) 2-(N,N-dimethylaminomethyl)chroman-4-one Dimethylaminoacetaldehyde diethyl acetal (40 g) was treated below -5° C. with conc. hydrochloric acid (196 ml) and then stirred at room temperature for 2 hours. After the solution had been neutralised with sodium bicarbonate, 2 N sodium hydroxide (80 ml) was added followed by 2-hydroxyacetophenone (34 g) in 2 N sodium hydroxide (80 ml) and sufficient dioxane to give a single phase reaction mixture. The solution was heated at 70°-80° C. with stirring for 21/2 hours and left at ambient temperature overnight. Extraction with diethyl ether was followed by extraction of the organic phase with dilute hydrochloric acid. The aqueous acid solution was basified with sodium hydroxide solution and extracted into diethyl ether to give the title compound (3.4 g) as an oil. 1 H nmr (CDCl3) delta: 8.1-6.9 (m, 4H); 4.9-4.4 (m, 1H); 3.0-2.5 (m, 4H); 2.3 (s, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In tetrahydrofuran; ethanol; water; at 40℃; for 24h;Industrial scale; | 10 mmol of hydroxyacetophenone and 10 mmol of 4- (di-p-toluidino) benzaldehyde were added to the reactor, and 50 ml of a mixed solution of ethanol and tetrahydrofuran in a volume ratio of 9: 1 Solvent,10 ml of aqueous potassium hydroxide solution (15percent wt) was added dropwise and the mixture was stirred at 40 ° C for 24 hours, poured into 500 ml of ice water, neutralized with dilute hydrochloric acid (1 M) until pH = 7, 100 ml of methylene chloride Extract 3 times.The extracts were washed three times with saturated brine and deionized water respectively, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to obtain the crude product.The crude product was recrystallized from ethanol to obtain pure chalcone-based fluorescence sensor TAPHP, the structural formula is as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65.17% | With potassium carbonate; In acetone; for 4h;Reflux; | General procedure: To a solution of various substituted phenols (1 mmol) in dry acetone (30 mL) K2CO3 (1 mmol)and compound 3 or 4 (1 mmol) were added. After being stirred for 4 h at reflux temperature, thereaction mixture was cooled, filtered, and concentrated under vacuum. Then the residue was dilutedwith 30 mL ethyl acetate and sequentially washed with 30 mL 1 M HCl, aq. NaHCO3 solution andbrine in order. The organic layer was dried over MgSO4 and concentrated in vacuo. Purification of theresidue by chromatography on silica gel furnished target compounds. 1H-NMR, 13C-NMR and massspectroscopy (MS) of compounds 5a-m and 6a-m are shown in Supplementary Materials. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With iodine; In dimethyl sulfoxide; at 20 - 110℃; for 2h; | 2.5 mL of o-hydroxyacetophenone was dissolved in 10 mL of DMSO, and 2.8 g of iodine was slowly added.Add 3.6g at room temperature with stirringa solution of <strong>[16313-65-8]2-amino-5-nitrobenzamide</strong> in 20 mL of DMSO,The reaction was carried out at 110 C for 2 h.150 mL of water was added to the reaction system.Extracted with (3 × 60 mL) ethyl acetate.The iodine was removed by washing with (2×40 mL) saturated NaHSO3 solution.After washing with water, dry with anhydrous magnesium sulfate.Evaporate the solvent under reduced pressure.The residue was separated by chromatography (eluent: ethyl acetate: petroleum ether = 1:3).2-(2-hydroxybenzoyl)-6-nitro-4(3H)-quinazolinone 4.5 g,Yield 73%, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With oxygen; copper diacetate; palladium diacetate; In dimethyl sulfoxide; at 120℃; under 760.051 Torr; for 23h; | General procedure: Pd(OAc)2 (9.00 mg, 0.04 mmol) and () (14.6 mg, 0.08 mmol) were placed in a screw-top test tube, and a solution of 3,4-dihydronaphthalen-l(2H)-one (8) (58.6 mg, 0.40 mmol) in DMSO (0.08 mL) was added at room temperature. Then 1,3-diaminopropane (6) (0.10 mL, 1.20 mmol) was added to the reaction mixture. The test tube was filled with oxygen and then the resulting mixture was stirred at 120 C for 16 h. After cooling down to room temperature, the palladium residue was removed by filtering through Celite. The organic solvent was removed under reduced pressure, and then the reaction was quenched by addition of 10% aqueous NH3 solution. The solution was extracted three times with a 4:1 mixture of hexane and EtOAc. The combined organic layers were washed with saturated aqueous NaCl solution, dried over anhydrous Na2S04, and filtered through Celite. The filtrate was concentrated to afford 5,6-dihydrobenzo[h]quinoline (9) (51.1 mg, 70%) as a yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With triethylamine; In dichloromethane; at 20℃; | General procedure: To a solution of paeonol/2-hydroxy acetophenone/3-methoxyphenol (1/2/3, 1.0 mmol) and ethanesulfonyl chloride/arylsulfonyl chloride (7, 1.2 mmol) in dry dichloromethane (CH2Cl2, 10 ml) at room temperature, a solution of triethylamine (Et3N) (1.5 mmol) in dry CH2Cl2 (5 ml) was added dropwise for 10 min. When the reaction was completed by TLC analysis, the reaction mixture was diluted with water (15 ml), and extracted with CH2Cl2 (30 ml*3). Subsequently, the combined organic phasewas washed by saturated aq. brine (30 ml), dried over anhydrous Na2SO4, concentrated in vacuo, and purified by silica gel column chromatography to obtain title compounds. The data for 4a-p, 5a-p, and 6a-p are shown as follows. |
Tags: 2'-Hydroxyacetophenone | Ketones | Phenols | Fluorinated Building Blocks | Aryls | Organic Building Blocks | By Structure | 118-93-4
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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 |
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The concentration of the dissolution solution you need to prepare is mg/mL