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CAS No. : | 33288-79-8 | MDL No. : | MFCD00451571 |
Formula : | C14H10O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FMYXOBBPXQZKKY-UHFFFAOYSA-N |
M.W : | 242.23 | Pubchem ID : | 458204 |
Synonyms : |
|
Num. heavy atoms : | 18 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 65.59 |
TPSA : | 74.6 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 : | Yes |
Log Kp (skin permeation) : | -5.88 cm/s |
Log Po/w (iLOGP) : | 1.14 |
Log Po/w (XLOGP3) : | 2.67 |
Log Po/w (WLOGP) : | 2.16 |
Log Po/w (MLOGP) : | 1.06 |
Log Po/w (SILICOS-IT) : | 2.3 |
Consensus Log Po/w : | 1.87 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.32 |
Solubility : | 0.116 mg/ml ; 0.000479 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.89 |
Solubility : | 0.0313 mg/ml ; 0.000129 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.67 |
Solubility : | 0.052 mg/ml ; 0.000215 mol/l |
Class : | Soluble |
PAINS : | 1.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.45 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
100% | Reflux | Step 1. Preparation of l 2-bis(4-hydroxyphenyl)ethane-l,2-dione 4,4'-dimethoxybenzil (2.0 g, 7.41 mmol) was dissolved in 30 mL of hydrogen bromide and 10 mL of acetic acid glacial. The reaction was stirred at reflux temperature overnight. The mixture was extracted with ethyl acetate and the organic phase was washed with water, dried over sodium sulphate. Concentration under vaccum gave the title compound as a yellow solid (1.9 g, quantitative). |
94% | With hydrogen bromide; acetic acid In water for 24 h; Reflux | Into a 100 mL round-bottomed two-necked flask equipped witha magnetic stirrer bar and a reflux condenser, 4,4'-dimethoxybenzil(2 g, 0.0075 mmol), aqueous HBr (15 mL, 48percent) and glacialacetic acid (15 mL) were placed. The reaction mixture was refluxedfor 24 h, after cooling to room temperature, was poured into100 mL water. Ethyl acetate was added to the mixture to give twophases of which the organic phase containing the product wasseparated and dried over magnesium sulfate for 12 h. The solventwas removed under reduced pressure and the obtained yellowprecipitate was washed thoroughly with water and then dried in avacuum oven at 80 8C. Yield: 94percent (1.7 g) and m.p.: 229–231 8C. FTIR(KBr) at cm 1: 3400 (OH phenol), 3045 (C–H aromatic), 1646(C55O), 1576 (C55C), 1223 (C–O). 1H NMR (400 MHz, DMSO-d6,): d6.91–6.95 (d, 4H, J = 8.0 Hz), 7.73–7.77 (d, 4H, J = 8.0 Hz), 10.84 (s,2H). |
94% | With hydrogen bromide In water; acetic acid for 24 h; Reflux | Into a 100 mL round-bottomed two-necked flask equipped with a magnetic stir bar and a reflux condenser, 4,4'-dimethoxy benzil (2 g, 0.0075 mol), aqueous HBr (15 mL, 48percent) and glacial acetic acid (15 mL) were placed. The reaction mixture was refluxed for 24 h, and then poured in 100 mL water after cooling to room temperature. Ethyl acetate was added to the mixture to give two phases of which the organic phase containing the product was separated and dried over magnesium sulfate for 12 h. The solvent was removed under reduced pressure and the obtained yellow precipitate was washed thoroughly with water and then dried in a vacuum oven at 80 °C. Yield: 94percent (1.7 g), and melting point: 229-231 °C. FT-IR (KBr) at cm-1: 3400 (OH phenol), 3045 (C-H aromatic), 1646 (C=O), 1576 (C=C), 1223 (C-O). 1H NMR (400 MHz, DMSO-d6,): δ 6.91-6.95 (d, 4H, J = 8.0 Hz), 7.73-7.77 (d, 4H, J = 8.0 Hz), 10.84 (s, 2H). |
90% | for 24 h; Reflux; Inert atmosphere | A mixture of 4,4'-dimethoxybenzil (2.50 g, 0.0092 mol), glacial acetic acid (25 mL), and HBr (30 mL) was refluxed for 12 h under N2. After cooling, 5 mL HBr was added and mixture was refluxed for another 12 h. Upon completion of the reaction (as witnessed by TLC), the medium was poured into 200 mL deionized water. The organic product was extracted with 220 mL ethyl acetate. The organic phase was thoroughly washed with water in order to remove all acids and then dried over magnesium sulfate. The product was obtained as crystal after evaporation of the solvent in a rotary evaporator. The yield after drying in a vacuum oven at 80 °C was 90percent (1.79 g) with melting point of 120 °C. FT-IR (KBr, cm 1): 3031 (OH stretching), 1633 (C55O stretching), 1612 (C55C stretching), 1226 (C–O–C stretching). 1H NMR (400 MHz, DMSO-d6): d = 10.84 (2H OH, s), 6.91–7.77 (8H, m) ppm. C14H10O4: calculated C, 69.42percent; H, 4.13percent; N, 0percent; found C, 69.38percent; H, 4.16percent; N, 0percent. m/e: 242.06, 243.06, 244.06. |
89% | at 180℃; for 48 h; | A mixture of 1,2-bis(4-methoxyphenyl)-ethane-1,2-dione prepared according to example 1 (7.275 g, 26.91 mmol) and pyridine hydrochlorate (15.55 g, 134.5 mmol) under an atmosphere of nitrogen is heated to 180° C. for 2 days. After returning to ambient temperature, the mixture is diluted with ethyl acetate and water. The aqueous phase is extracted with ethyl acetate and the recombined organic phases are dried on magnesium sulfate, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography on a silica gel (petroleum ether/ethyl acetate 10/1 to 2/1) to yield 5.789 g (89percent) of a white solid. δH (300 MHz, MeOH-d) 6.91 (d; J 9.0; 4H), 7.82 (d; J 9.0; 4H). |
75% | With hydrogen bromide; acetic acid In water for 12 h; Reflux | The synthesis of 2 needs two steps. Firstly, a mixture of 1,2-bis(4-methoxyphenyl) ethane-1,2-dione (3 g, 11 m mol), glacial acetic acid (30 ml) and HBr (48percent, 100 ml) were added into a three-neck round bottom flask orderly, heated to reflux and stirred for 12 h. Then the mixture was cooled to room temperature and brown precipitation was observed. Then the precipitate was separated by filtration and washed with distilled water three times to give 1,2-bis(4-hydroxyphenyl) ethane-1,2-dione, yield: 75percent. Secondly, 1,2-bis(4-hydroxyphenyl) ethane-1,2-dione (2.0 g, 8.2 m mol), 1 - bromine decane (4.04g, 3.78 ml),anhydrous potassium carbonate (2.4g, 0.24 mol) and Tetra-nbutylammoniumbromide (1.33 g, 4.13 m mol) were dissolved in DMF (120 ml). The solution was heated to 120 deg.C and reacted for 90 min. After reaction, the solution was cooled to room temperature, added with water, oscillated by ultrasonic instrument.The cream-color deposit was filtered and washed by distilled water several times to give the target product (2) with a high productivity (about 90percent). |
4 g | With hydrogen bromide; acetic acid In water at 70 - 110℃; for 70 h; | Synthesis Example 1 Synthesis of 4,4′-dihydroxybenzil (0057) 4,4′-Dimethoxybenzil (5.0 g) was dissolved in acetic acid (95 mL). To the solution, 48 mass percent aqueous HBr (31.2 g) was added dropwise at 70° C. over 10 minutes. After addition of HBr, the mixture was stirred at 110° C. for 70 hours. Subsequently, water (150 g) was added to the mixture, to thereby crystallize the product. The crude crystals were recovered through filtration and washed with water (250 g), followed by drying, to thereby yield 4.0 g of 4,4′-dihydroxybenzil as a target product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With calcium hydride; diphenyldisulfane In 1-methyl-pyrrolidin-2-one for 1.5 h; Reflux | 1 mmol of 2-hydroxy-1,2-bis (4-methoxyphenyl) ethanone, dissolved in 0.8 mlIn N-methylpyrrolidone,At room temperature, 1.2 mmol of diphenyl disulfide,3.2 mmol of calcium hydride and 1.2 mL of N-methylpyrrolidone,After 1.5h reflux,Ether extraction, washed with dilute sodium hydroxide solution several times, the combined aqueous phase was acidified, extracted with ethyl acetate, dried, dried, and further purified by column chromatography,1,2-bis (4-hydroxyphenyl) ethane-1,2-dione in 80percent yield; |
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