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CAS No. : | 91136-43-5 | MDL No. : | MFCD17012437 |
Formula : | C11H8O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PLCQXZXTFCITAJ-UHFFFAOYSA-N |
M.W : | 172.18 | Pubchem ID : | 13225222 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
45% | Sodium hydride (115 mg, 2.64 mmol) was suspended in N,N-dimethylformamide (20 mL), and known <strong>[91136-43-5]3-hydroxy-1-naphthaldehyde</strong> [Tetrahedron, 1999, Vol. 55, p.5821-5830] (250 mg, 1.45 mmol) was added at 0C. After stirring for 30 minutes, iodomethane (230 muL, 3.69 mmoL) was added, and the mixture was stirred at room temperature for one hour. A saturated ammonium chloride aqueous solution (20 mL) was added to the reaction solution, followed by extraction with diethyl ether (50 mL). The organic layer was washed with brine and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate = 10/1) to give the target compound (122 mg, yield: 45%) as a light yellow solid. 1H-NMR (CDCl3, 500MHz):delta ppm: 4.86 (3H, s), 7.38 (1H, m), 7.55-7.51 (2H, m), 7.64 (1H, m), 7.79 (1H, m), 9.90 (1H, m), 10.35 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With pyridine; at 20℃; for 17h; | Known <strong>[91136-43-5]3-hydroxy-1-naphthaldehyde</strong> [Tetrahedron, 1999, Vol. 55, p.5821-5830] (300 mg, 1.74 mmol) was dissolved in pyridine (3 mL). Dimethylcarbamoyl chloride (750 muL, 8.15 mmol) was added, and the mixture was stirred at room temperature for 17 hours. A saturated ammonium chloride aqueous solution (10 mL) was added to the reaction solution, followed by extraction with diethyl ether (40 mL). The organic layer was washed with brine and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate = 4/1) to give the target compound (378 mg, yield: 89%) as a light yellow oil. 1H-NMR (CDCl3,400MHz):delta ppm: 3.06 (3H, s), 3.17 (3H, s), 7.55 (1H, m), 7.62(1H, m), 7.85-7.80 (3H, m), 9.15 (1H, d, J=8.6Hz), 10.34 (1H, s). MS (EI) m/z: 243 (M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; for 4h; | Known <strong>[91136-43-5]3-hydroxy-1-naphthaldehyde</strong> [Tetrahedron, 1999, Vol. 55, p.5821-5830] (233 mg, 1.35 mmol) was dissolved in pyridine (10 mL) and acetic anhydride (5 mL), and the mixture was stirred for four hours. The solvent was evaporated under reduced pressure, and the resulting residue was directly used for the next reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
~ 100% | Sodium hydride (1.38 g, 31.6 mmol) was suspended in tetrahydrofuran (100 mL), and known <strong>[91136-43-5]3-hydroxy-1-naphthaldehyde</strong> [Tetrahedron, 1999, Vol. 55, p.5821-5830] (3.50 g, 20.3 mmol) was added at 0C. After stirring for 30 minutes, N-phenyl-bis(trifluoromethanesulfonimide) (7.30 g, 20.4 mmoL) was added, and the mixture was stirred at 0C for 1.5 hours. A saturated ammonium chloride aqueous solution (100 mL) was added to the reaction solution, followed by extraction with diethyl ether (200 mL). The organic layer was washed with brine and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (elution solvent: hexane/diethyl ether = 5/1) to give the target compound (6.50 g, yield: ~100%) as a light yellow solid. 1H-NMR (CDCl3, 400MHz):delta ppm: 7.69 (1H, m), 7.77 (1H, m), 7.87 (1H, brd, J=2.7Hz), 7.95 (1H, brd, J=8.2Hz), 8.00 (1H, brd, J=2.7Hz), 9.17 (1H, d, J=8.6Hz), 10.42 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With ammonium acetate; titanium(IV) oxide; at 120℃; | General procedure: A mixture of hydroxyl naphthaldehyde (1mmol), phenanthrene-9,10-dione (1mmol), naphthylamine (1mmol), ammonium acetate (1mmol) and TiO2 (1mol%) was stirred at 120C with continuous stirring with a bar magnet. The progress of the reaction was monitored by TLC (Scheme S4). After completion of the reaction, 10ml ethyl acetate was added to the reaction mixture and shaken well to dissolve the organic components and the mass filtered to separate out TiO2 and the residue was washed with ethyl acetate. The solid TiO2 residue was further washed with hot acetone and then dried up. The product was purified by column chromatography using benzene:ethyl acetate (9:1) as the eluent. The newly synthesised phenanthrimidazoles have been characterized by 1H and 13C NMR and mass (MS) spectra. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With copper doped mesoporous silica MCM-41 supported dual acidic ionic liquid-HSO4; In ethanol; at 80℃; for 1h; | General procedure: In a typical process, 0.05 mol aromatic aldehyde, 0.05 mol ethylacetoacetate, 0.05 mol urea, 10 mL EtOH, and 0.5 g (0.5)IL-HSO4MCM-41Cu(15) were mixed and stirred at 80 C for the desiredtime. After the completion of the reaction,monitored by LC-MS, the solutionwascooled down to roomtemperature and centrifugalized to obtainthe catalyst. The catalyst was washed with ethanol for reuse. Thefiltrate was concentrated under reduced pressure to give the correspondingpure product. Fresh substrates were then recharged to the recoveredcatalyst and then recycled under identical reaction conditions.The productswere identified by 1H NMR, LC-MS and Elemental analysis,and the characterization data and spectras are provided in thesupporting information. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With acetic acid; In ethanol; for 5h;Inert atmosphere; Reflux; | To the mixture of AP-BODIPY (72 mg, 0.2 mmol) and <strong>[91136-43-5]3-hydroxy-1-naphthaldehyde</strong> (40 mg, 0.24 mmol) dissolved in EtOH (20 ml), twodrops of glacial acetic acid were added under N2 atmosphere. The resulting reaction mixture was refluxed for 5 h and then cooled to roomtemperature. The red precipitate was filtrated and washed by EtOH.Recrystallization from CHCl3 and MeOH yielded pure sample of NAPBODIPYas red powder, 57 mg, 56%. 1H NMR (DMSO, 400 MHz): delta15.75 (d, 1H, J=8 Hz), 10.74 (s, 1H), 9.61 (d, 1H, J=12 Hz), 8.46 (d,1H, J=8 Hz), 8.18 (s, 1H, J=8 Hz), 7.84 (d, 1H, J=8 Hz), 7.70 (d,1H, J=8 Hz), 7.51 (t, 1H, J=12 Hz), 7.30 (t, 1H, J=12 Hz), 6.97 (d,1H, J=12 Hz), 6.92 (s, 1H), 6.82 (d, 1H, J=8 Hz), 6.21 (s, 2H), 2.46(s, 6H), 1.54 (s, 6H); 13C NMR (100 MHz, DMSO) delta178.2, 155.4, 140.0,149.6, 143.2, 141.8, 138.8, 134.3, 132.3, 131.1, 130.0, 129.5, 128.7,126.5, 125.4, 123.8, 121.9, 120.5, 119.8, 118.9, 115.6, 108.2, 14.7,14.6; MS (MALDI-TOF): one isotopic cluster peaking at m/z 509.13(Calcd. For M+ 509.21); Anal. Calcd for C30H26BF2N3O2: C, 70.74; H,5.15; N, 8.25. Found: C, 70.56; H, 5.31; N, 8.35. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
250 mg | With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; | To a stirred a solution of 3 -hydroxy- l-naphthaldehyde (250 mg, 1.45 mmol) in DMF ( 6.0 mL) was added cesium carbonate (1.5 g, 4.36 mmol) followed by 2- (chloromethyl)pyrimidine hydrogen chloride (238 mg, 1.45 mmol). The reaction mixture was stirred at room temperature. After reaction completion, quenched with water and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and evaporated under reduced pressure to give the crude compound which purified using combi flash with 30% Ethyl acetate in Hexane as an eluent to get pure compound. 250 mg, LCMS: 265 (M+l)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100 mg | With 2-Picolinic acid; potassium phosphate; copper(l) iodide; In dimethyl sulfoxide; at 120℃; for 16h; | To a stirred solution of 3 -hydroxy- l-naphthaldehyde (250 mg, 1.45 mmol) in DMSO, were added potassium phosphate (630 mg, 2.90 mmol), 2-bromopyridine (455 mg, 2.90 mmol) Copper iodide (26.6 mg, 0.14 mmol) and picolinic acid (17.2 mg, 0.14 mmol). Then the reaction mixture stirred at l20C for 16 h. After reaction completion, cooled to rt, quenched with water and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and evaporated under reduced pressure to give the crude compound which purified using combi flash with 25% Ethyl acetate in Hexane as an eluent to get pure compound 100 mg, LCMS: 250.1 (M+l)+. |
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