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CAS No. : | 84-59-3 | MDL No. : | MFCD00021473 |
Formula : | C10H6Br2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GHJUWGHWJYULLK-UHFFFAOYSA-N |
M.W : | 317.96 | Pubchem ID : | 96260 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
83% | Stage #1: at 80℃; Inert atmosphere Stage #2: With bromine In acetic acid for 12 h; Reflux |
synthesis of 2,6-dibromo-1,5-dihydroxynaphthaleneUnder a nitrogen atmosphere, 1,5-dihydroxynaphthalene (5.0 g, 31 mmol) and a little amount of iodine were dissolved in acetic acid (150 ml). This solution was heated to a temperature of 80° C. Note that acetic acid was used as a solvent.Bromine (3.2 ml, 62.4 mmol) was dripped in the solution, and reaction was carried out under a reflux temperature for 12 hours. The reaction solution was cooled to a room temperature, and pure water (50 ml) was added thereto. A precipitated solid was separated and collected by filtering. This solid substance was rinsed by pure water, and dried under a reduced pressure condition, thereby obtaining a white solid of 2,6-dibromo-1,5-dihydroxynaphthalene (8.2 g, yield: 83percent).The reaction formula of the above-explained reaction is as follow. Various spectrum data of the obtained 2,6-dibromo-1,5-dihydroxynaphthalene are indicated below.1H-NMR (400 MHz, CDCl3) δ5.99 (s, 2H, OH), 7.39 (d, 2H, J=9.4 Hz, ArH), 7.70 (d, 2H, J=9.4 Hz, ArH); EIMS (70 eV) m/z=318 (M+) |
80% | With N-Bromosuccinimide In N,N-dimethyl-formamide; acetonitrile at 20℃; | Example 17 - 2,6-dibromonaphthalene-l,5-diol [00139] To a suspension of naphthalene-l ,5-diol (1 15.2 g) in CH3CN (800 mL) was added DMF solution (400 mL) of NBS (254 g) dropwise and the mixture was stirred at room temperature and monitored by GCMS. Water was added quench the reaction. The resulting precipitate was collected by filtration and washed with water to give 2,6-dibromonaphthalene-l ,5-diol (80percent) LRMS (ESI): Calcd. For Ci0H6Br2O2: 317.9614, Found: 317.9. |
80% | at 70℃; for 1 h; | Naphthalene-1,5-diol (20 g, 13.0 mmol) and a catalytic amount of iodine were mixed in glacial acetic acid (600 mL). The mixture was then heated to 70oC and bromine (13.0 mL) in glacial acetic acid (50 mL) was added dropwise during the course of 60 minutes. The mixture was then cooled to room temperature. The crude compound was filtered and washed with water to get a green solid in a yield of 80percent. 1H NMR (600 MHz, CDCl3): δ 7.71 (d, J = 8.7 Hz, 2H, ArH), 7.51 (d, J = 8.7 Hz, 2H, ArH), 5.97(s, 2H, -OH). 13C NMR (150 MHz, CDCl3): δ 148.09, 128.76, 124.71, 115.87, 105.40. Mass spectrum (EI, M+): 315 m/z. |
77% | With bromine; iodine In acetic acid at 80℃; | After dihydroxynaphthalene (20.0 g, 0.125 mol) was dissolved in acetic acid (550 mL), a catalytic amount of I2 was added and the flask was heated to 80°C. Br2 (40 g, 0.25mol) dissolved in acetic acid was slowly dropped into this mixture. The mixture was cooled to room temperature, and the crude solid product was filtered. The product was purified in petroleum ether. Yield: 31.77 g (80percent). |