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CAS No. : | 85575-93-5 | MDL No. : | MFCD02093459 |
Formula : | C20H24N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LSGGPELKXXFMGO-UHFFFAOYSA-N |
M.W : | 292.42 | Pubchem ID : | 13384176 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
Compound 2 was synthesized in a similar fashion to compound 1 using 1,10-phenanthroline (0.59 g, 3.26 mmol) and n-butyl-lithium (8.16 ml of 1.6 M in hexanes, 12.94 mmol) [ 13]. The crude amber oil was purified using flash chromatography (basic alumina; 100% hexane wash; 100% CH2Cl2 wash; elution with 4% methanol in CH2Cl2) to yield a pale yellow oil. 1H NMR chemical shifts, peak multiplicities and peak integrations, and UV-vis absorption maxima have been previously reported [13]. |
Yield | Reaction Conditions | Operation in experiment |
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Specific examples of the compound of formula (ii) include, for example, 2,9-dimethyl-4,7-diphenyl-1;10-phenanthroline, 2,9-dimethyl-1,10-phenanthroline, ... 5,6-dimethyl-1,10-phenanthroline, 1,10-phenanthroline-2,9-dimethanol, and 2,9-di-n-butyl-1,10-phenanthroline. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; for 1h;Reflux; Inert atmosphere; | Under argon atmosphere, <strong>[85575-93-5]2,9-di-n-butyl-1,10-phenanthroline</strong> (63.8 mg, 0.218 mmol) was added to 5 mL of the suspension of silver(I) tetrafluoroborate (42.5 mg, 0.218 mmol) in dry dichloromethane, and the mixture was heated to reflux with stirring for one hour. Then, 2-pyridine-2-yl-1H-indole (42.4 mg, 0.218 mmol) was added to the resulting colorless solution, which was heated to reflux with stirring for additional two hours. The obtained black precipitate suspension was filtrated. The filtrate was concentrated, and the residue was dissolved in 2 mL of methanol and subjected to recrystallization by slow evaporation. The precipitated colorless prismatic crystal was filtrated, and the filtrated matter was vacuum-dried to provide 47.5 mg of the colorless solid complex. [Show Image] Based on the NMR measurement, it was confirmed that the material ligand (compound) was lost and the obtained complex did not contain the unit derived from 2-pyridine-2-yl-1H-indole. The NMR data and the data of CHN elemental analysis of the complex are provided below. 1H NMR (300 MHz, CDCl3) δ8.55 (d, J= 8.4 Hz, 2H), 8.04 (s, 2H), 7.79 (d, J= 8.4 Hz, 2H), 2.97 (t, J = 7.8 Hz, 4H), 1.62-1.51 (m, 4H), 0.91-0.79 (m, 6H), 0.38 (t, J = 7.2 Hz, 6H); 13C NMR (75 MHz, CDCl3) δ 162.5 (d, J = 1.7 Hz), 142.2 (d, J = 2.4 Hz), 139.0 (s), 128.0 (d, J = 2.0 Hz), 126.5 (s), 124.4 (d, J = 2.4 Hz), 41.9 (s), 32.5 (s), 22.4 (s), 13.2 (s); Anal. Calcd for C40H48N4AgBF4·H2O: C, 60.24; H, 6.32; N, 7.03. Found: C, 60.06; H, 5.89; N, 7.23. The composition of the complex was determined according to the values of CHN elemental analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Under argon atmosphere, 2-dimethylamino-2'-(diphenylphosphino)biphenyl (34.3 mg, 0.0899 mmol) was added to 5 mL of the suspension of silver(I) tetrafluoroborate (17.5 mg, 0.0899 mmol) in dry dichloromethane, and the mixture was heated to reflux with stirring for one hour. Then, 2,9-di-n-butyl-1,10-phenanthroline (26.3 mg, 0.0899 mmol) was added to the obtained solution, which was heated to reflux for additional one and half hours. The reaction solution was filtrated, and the filtrate was concentrated and then the residue was dissolved in chloroform followed by slow diffusion of diethylether. The pale yellow precipitate was filtrated, and the filtrated matter was subjected to vacuum drying, thereby providing 45.0 mg of the pale yellow solid complex. The result of elemental analysis for the obtained complex is shown in Table 2-1, and the composition ratio of the complex was obtained. The present complex corresponds to the above composition formula (1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: 1.0 mmol of [Cu(CH3CN)4]BF4 and2.0 mmol of PPh3 were dissolved in 10 mL of CH2Cl2. The mixture was refluxed for 30 min at room temperature. Then 1.0 mmol of Phen was added. The mixture was refluxed for another half hour.The solvent was removed by rotary evaporation. The crude product was further purified by recrystallization from the mixed solvent of tetrahydrofuran/ether. Yield: 85%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | General procedure: 1.0 mmol of [Cu(CH3CN)4]BF4 and2.0 mmol of PPh3 were dissolved in 10 mL of CH2Cl2. The mixture was refluxed for 30 min at room temperature. Then 1.0 mmol of Phen was added. The mixture was refluxed for another half hour.The solvent was removed by rotary evaporation. The crude product was further purified by recrystallization from the mixed solvent of tetrahydrofuran/ether. Yield: 85%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | General procedure: [Ir(ppy)2Cl]2 (0.069 g, 0.064 mmol)and 2,9-dimethyl-1,10-penanthroline (0.027 mg, 0.128 mmol) were heated to reflux in an ethylene glycol solution (20 ml) for 16 h. The mixture was transferred into a separation funnel with water (90 ml) and washed through three extractions with diethyl ether (60 ml).A concentrated solution of ammonium hexafluorophosphate in water was slowly added intothe aqueous layer, yielding a colored suspension. The precipitate was collected by filtration[13] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | In dichloromethane; | ompound 1 by reacting 51.0 mg (0.174 mmol) of <strong>[85575-93-5]2,9-di-n-butyl-1,10-phenanthroline</strong> and 23.0 mg (0.174 mmol) of anhydrous CuCl2.This complex was isolated as red/orange crystals after recrystallizationfrom acetonitrile at -10 C over a two day period (43 mg, 58% yield).Elemental analysis indicated the complexwas isolated as an acetonitrileadduct. Elemental analysis (C20H24N2Cl2Cu·CH3CN): Calculated: C =56.47%, H = 5.82%; Experimental: C = 56.90%, H = 5.61%. IR: νmax/cm-1 3341 (w), 3039 (CH), 2953 (CH), 2925 (CH), 2856 (CH),1442, 850, 672. UV-vis: λmax (DMSO, 20 C)/nm (ε, M-1 cm-1)243 (22,543), 279 (14,701), 296 (Sh, 8434), 463 (Sh, 987), 781(64). Mass spectrometry: Molecular ion (m/z): [Cu(di-n-butylphen)(Cl)]+ = 390.0908 amu (theoretical = 390.0919 amu);[Cu2(di-n-butylphen)2(Cl)3]+ = 815.1561 amu (theoretical =815.1531 amu). |