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CAS No. : | 626-00-6 | MDL No. : | MFCD00041731 |
Formula : | C6H4I2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | SFPQFQUXAJOWNF-UHFFFAOYSA-N |
M.W : | 329.91 | Pubchem ID : | 12270 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
76% | Step A: A solution of 1,3-diiodobenzene (3.0 g, 9.09 mmol) in dry THF (40 mL) was cooled to -78° C. under a nitrogen before addition of n-butyl lithium (1.6 M in hexane, 5.6 mL, 9.09 mmol) dropwise over 10 min. The reaction mixture was stirred for 30 min and then a solution of <strong>[22929-52-8]dihydrofuran-3(2H)-one</strong> (782 mg, 9.09 mmol) in THF (3 mL) added over 5 min. The reaction mixture was stirred for 1 h at -78° C. then poured into saturated NH4Cl solution. The mixture was extracted with ethyl acetate and the organic layer dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 9:1 hexanes/ethyl acetate) to give 3-(3-iodophenyl)tetrahydrofuran-3-ol (2.0 g, 76percent) as a colorless liquid: 1H NMR (CDCl3, 300 MHz) delta 7.87 (t, J=1.8 Hz, 1H), 7.64 (td, J=7.8 Hz, 1H), 7.45 (td, J=7.8 Hz, 1H), 7.10 (t, J=8.1 Hz, 1H), 4.26-4.06 (m, 2H), 3.98-3.82 (m, 2H), 2.46-2.32 (m, 1H), 2.30-2.21 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With potassium carbonate; triphenylphosphine; palladium dichloride; at 70℃; for 24h;Sealed tube; | General procedure: A mixture of dihaloarene (0.4 mmol), arylboronicacid (0.4 mmol), K2CO3 (0.8 mmol), PdCl2 (7 mol %),PPh3 (15 mol %), and PEG-400 (2 mL) in a sealed tubewas stirred in air at 70C for the desired time until completeconsumption of starting material as monitored byTLC. After that the mixture was poured into ethyl acetate,then washed with water, extracted with ethyl acetate, driedby anhydrous Na2SO4, then fi ltered and evaporated undervacuum, the residue was purifi ed by fl ash column chromatography(petroleum ether or petroleum ether/ethylacetate) to afford the corresponding coupling products |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | General procedure: 5H-benzofuro[3,2-c]carbazole (5.00 g, 19.43 mmol), 1,3-diiodobenzene (3.05 g, 9.25 mmol), copper(I) iodide (0.18 g,0.93 mmol), and tripotassium phosphate (4.32 g, 20.36 mmol) weredissolved in 1,4-dioxane (80 mL) and then added to the flask. Afterstirring for 1 h at room temperature under a nitrogen atmosphere, a(±)-trans-1,2-cyclohexanediamine (0.11 g, 0.93 mmol) was added.The reaction mixturewas stirred for 48 h at 100 C, and the reactionwas quenched with toluene (300 mL). The solvent was removed byrotary evaporation, and the crude product was washed with water.Impurities were removed by column chromatography on silica gelusing dichloromethane/n-hexane. Additionally, BFCz was purifiedby sublimation under a vacuum. As a result, the title compoundwasobtained as a white powder. The results are as follows: |