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CAS No. : | 581-43-1 | MDL No. : | MFCD00004082 |
Formula : | C10H8O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MNZMMCVIXORAQL-UHFFFAOYSA-N |
M.W : | 160.17 | Pubchem ID : | 93552 |
Synonyms : |
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Chemical Name : | Naphthalene-2,6-diol |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | 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 |
---|---|---|
97% | With N-Bromosuccinimide; In tetrahydrofuran; at 0 - 60℃; for 3h; | In a more detailed embodiment, the method begins by taking a solution of 2,6-naphthalene diol (10.16 g, 63.43 mmol) in tetrahydrofuran (110 mL) and cooling the solution to about 0 C., then treated slowly with N-bromosuccinimide (22.58 g, 0.13 mol). The flask was then topped with a water condenser and heated to around 60 C. for around 3 hours, then cooled to room temperature. This reaction mixture A was diluted with a saturated aqueous Na2S2O3 solution (250 mL) and water (1.5 L), and the resulting solid was collected by filtration, and then left under vacuum for around 18 hours. The desired product, (0082) (19.5 g, 0.061 mol, 97% yield), was obtained as a tan solid. The 1H NMR spectrum of (0083) is shown in FIG. 2. |
97% | With N-Bromosuccinimide; In tetrahydrofuran; at 0 - 60℃; for 3h; | In a more detailed embodiment of producing al,2,5,6-naphthalenediimide monomer, the method can begin by taking a solution of 2,6-naphthalene diol (10.16 g, 63.43 mmol) in tetrahydrofuran (110 mL) and cooling the solution to about 0 C, then treated slowly with N- bromosuccinimide (22.58 g, 0.13 mol). The flask was then topped with a water condenser and heated to around 60C for around 3 hours, then cooled to room temperature. This reaction mixture A was diluted with a saturated aqueous Na2S203 solution (-250 mL) and water (-1.5 L), and the resulting solid was collected by filtration, and then left under vacuum for around 18 hours. The desired product, mol, 97% yield), was obtained as a tan solid. The 1H NMR spectrum of is shown in Figure 2. |
90% | With N-Bromosuccinimide; In tetrahydrofuran;Reflux; | Example 1 - l,5-dibromonaphthalene-2,6-diol [00123] To a solution of naphthalene -2, 6-diol (1) (5.1 g) in 50 mL of Tetrahydrofuran (THF), was added N-Bromosuccinimide (NBS, 1 1.4 g). The mixture was re fluxing and monitored by GCMS. The reaction was quenched with saturated sodium thiosulfate, and filtered. The solid was washed by water to afford 1 ,5- dibromonaphthalene-2,6-diol (90%). LRMS (ESI): Calcd. for Ci0H6Br2O2: 317.8714, Found: 317.9. |
With bromine; In acetic acid; at 120 - 125℃; | Synthesis of 1,3,5,7-tetrabromo-2,6-dihydroxynaphthalene2,6-dihydroxynaphthalene (2 g, 12.5 mol) was dissolved in acetic acid (60 ml). The acetic acid was used as a solvent. Bromine (2.6 ml. 50.7 mol) was dripped in the solution, and reaction was carried out under a reflux temperature (120 C. to 125 C.).As is explained in the embodiment for carrying out the present invention, in this stage, first and fifth hydrogen atoms with a high reactivity among hydrogen atoms contained in 2,6-dihydroxynaphthalene were substituted by bromine atoms, and 1,5-dibromo-2,6-dihydroxynaphthalene was merely produced. In order to obtain naphthodithiophene having a linear structure at last, it was further necessary to substitute the third and seventh hydrogen atoms with bromine.Next, bromine (2.6 ml) was further dripped into the reaction solution by five times at total, and iron powders (50 mg, 1.3 mol) as a catalyst were added thereto, and reaction was caused for 76 hours.Next, 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 acetone, dried under a reduced pressure condition, thereby obtaining a rough product.The obtained rough product was caused to be recrystallized using 1,4-dioxane as a solvent, and purified. Accordingly, 1,3,5,7-tetrabromo-2,6-dihydroxynaphthalene (3.0 g, yield: 51%) with colorless needle crystals was obtained.As explained above, by dripping bromine several times and by adding iron powders as a catalyst, 1,3,5,7-tetrabromo-2,6-dihydroxynaphthalene was synthesized at a high yield.The reaction formula of the above-explained reaction is as follow. Various spectrum data of the obtained 1,3,5,7-tetrabromo-2,6-dihydroxynaphthalene are indicated below.1H-NMR (270 MHz, CDCl3) delta6.18 (s, 2H, OH), 8.31 (s, 2H, ArH); EIMS (70 eV) m/z=476 (M+) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; | STR66 46.8 g (0.19 mole) of 3,4,5-trichloro-benzotrifluoride are added slowly and with stirring to a mixture which consists of 56.8 g (0.36 mole) of 2,6-dihydroxynaphthalene, 14.3 g (0.36 mole) of pulverulent sodium hydroxide and 170 ml of dimethyl sulphoxide and which has been heated to 120 C., and the reaction mixture is then stirred at 120 C. for approximately 3 hours and further at 20 C. for approximately 15 hours. The reaction mixture is then diluted with water to twice the volume, and acidified with 1N hydrochloric acid. The precipitate obtained is separated off and extracted with toluene, and the organic phase is separated off, washed with water, dried over sodium sulphate and filtered. The solvent is distilled off the filtrate in a waterpump vacuum. The residue is recrystallized from ethanol. 52 g (74% of theory) of 6-(2,6-dichloro-4-trifluoromethyl-phenoxy)-2-naphthol of melting point 158 C. are obtained. The starting substances of the formula (II) listed in Table 2 below can be prepared in analogy with Example (II-1). |