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CAS No. : | 56052-26-7 | MDL No. : | MFCD06658378 |
Formula : | C11H9BrO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 237.09 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 |
---|---|---|
84% | With sulfuric acid; chromium(VI) oxide In water; acetone at 0 - 20℃; for 2 h; | To a solution of (4-bromo-1-naphthyl)methanol (1.329 g, 6.027 mmol) in acetone (50 ml) was added dropwise slowly a solution of chromic anhydride (1.81 g, 18.1 mmol) and conc. sulfuric acid (2 ml) dissolved in water (9 ml) under ice-cooling. After the completion of the dropwise addition, the mixture was stirred at room temperature for 2 hrs. Acetone of the reaction solution was evaporated under reduced pressure. The residue was diluted with ethyl acetate, washed three times with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was crystallized from ethanol-water to give the objective substance. pale-brown crystal yield 1.272 g, 84percent mp 223-224°C; 1H-NMR (CDCl3-DMSO-d6, 200MHz) δ 7.60-7.69 (2H, m) , 7.83 (1H, d, J = 7.8 Hz), 8.06 (1H, d, J = 8.2 Hz), 8.28-8.36 (1H, m), 8.99-9.08 (1H, m); IR (KBr) 3100-2500, 1694, 1566, 1508, 1279, 1252, 1190, 903, 785, 762 cm-1; Anal. Calcd for C11H7BrO! 2: C, 52.62; H, 2.81. Found: C, 52.42; H, 2.87. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With silica gel; pyridinium chlorochromate In dichloromethane at 20 - 25℃; for 2 h; | Step 2. 4-bromonaphthalene-1-carbaldehyde Into a 250-mL round-bottom flask, was placed dichloromethane (150 mL), (4-bromonaphthalen-1-yl)methanol (6.3 g, 26.57 mmol, 1.00 equiv), PCC (11.4 g, 183.72 mmol, 2.00 equiv) and 20 g Silicon dioxide. The resulting solution was stirred for 2 h at room temperature. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and washed with ethyl acetate/petroleum ether (1/10-1/5). This resulted in 5.3 g (85percent) of 4-bromonaphthalene-1-carbaldehyde as a white solid. |