Structure of 1202564-31-5
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 1202564-31-5 |
Formula : | C16H9ClN2 |
M.W : | 264.71 |
SMILES Code : | ClC1=NC2=C(C=CC=C3)C3=C(C=CC=C4)C4=C2N=C1 |
MDL No. : | MFCD28405117 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H320-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
* 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 |
---|---|---|
69% | With palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine; In ethanol; water; toluene; at 80℃; for 12h;Inert atmosphere; | This example shows a method of synthesizing 2-[4-(naphthalen-1-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: NPDBq) represented by the following structural formula (101). In a 200 mL three-neck flask, a mixture of 2.7 g (10 mmol) of 2-chlorodibenzo[f,h]quinoxaline, 2.7 g (11 mmol) of 4-(1-naphthyl)phenylboronic acid, 23 mg (0.1 mmol) of palladium(II) acetate, 91 mg (0.3 mmol) of tri(ortho-tolyl)phosphine, 43 mL of toluene, 4 mL of ethanol, and 14 mL of an aqueous solution of potassium carbonate (2 mol/L) was degassed while being stirred under reduced pressure, and was then reacted by being heated and stirred under a nitrogen atmosphere at 80 C. for 12 hours. After the reaction, 500 mL of toluene was added to this reaction mixture solution, and an organic layer of the mixture solution was filtered through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), alumina (produced by Merck & Co., Inc., neutral), and Celite (produced by Wako Pure Chemical Industries, Ltd., catalog No. 531-16855). The obtained filtrate was washed with water, and magnesium sulfate was added thereto so that moisture was adsorbed. This suspension was filtered to obtain a filtrate. The resulting filtrate was concentrated, followed by purification using silica gel column chromatography. At this time, a mixed solvent of toluene and hexane in a ratio of 1:5 was used as a developing solvent for the chromatography. The obtained fraction was concentrated, and methanol was added thereto. The mixture was irradiated with supersonic and then recrystallized, so that the objective substance was obtained as 3.0 g of yellow powder in a yield of 69%. The Rf values of the objective substance and 2-chlorodibenzo[f,h]quinoxaline were respectively 0.33 and 0.55, which were found by silica gel thin layer chromatography (TLC) (with a developing solvent of ethyl acetate and hexane in a ratio of 1:10). A nuclear magnetic resonance (NMR) method identified this compound as 2-[4-(naphthalen-1-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: NPDBq), which was the objective substance. 1H NMR data of the obtained substance are as follows: 1H NMR (CDCl3, 300 MHz): delta (ppm)=7.47-7.62 (m, 4H), 7.75-8.03 (m, 9H), 8.50 (d, J=8.3 Hz, 2H), 8.68 (d, J=7.3 Hz, 2H), 9.27 (d, J=7.8 Hz, 1H), 9.46-9.50 (m, 2H). The 1H NMR chart is shown in FIGS. 10A and 10B. Note that FIG. 10B is a chart showing an enlarged part of FIG. 10A in the range of 7.00 ppm to 9.60 ppm. Further, FIG. 11A shows an absorption spectrum of a toluene solution of NPDBq, and FIG. 11B shows an emission spectrum thereof. In addition, FIG. 12A shows the absorption spectrum of a thin film of NPDBq, and FIG. 12B shows the emission spectrum thereof. The measurement of the absorption spectrum was conducted by using a UV-visible spectrophotometer (V-550, produced by JASCO Corporation). The measurements were performed with samples prepared in such a manner that the solution was put in a quartz cell and the thin film was obtained by evaporation onto a quartz substrate. The absorption spectrum of the solution was obtained by subtracting the absorption spectra of quartz and toluene from the spectrum of the solution, and the absorption spectrum of the thin film was obtained by subtracting the absorption spectrum of a quartz substrate from the spectrum of the thin film. In FIGS. 11A and 11B and FIGS. 12A and 12B, the horizontal axis represents wavelength (nm) and the vertical axis represents intensity (arbitrary unit). In the case of the toluene solution, an absorption peak was observed at around 377 nm, and an emission wavelength peak was 398 nm. In the case of the thin film, an absorption peak was observed at around 385 nm, and emission wavelength peaks were 429 nm, 445 nm, and 488 nm (at an excitation wavelength of 378 nm). Electrochemical characteristics of a thin film of NPDBq were measured (the measuring instrument was AC-2 produced by Riken Keiki, Co., Ltd.). Note that the measurement of electrochemical characteristics of the thin film was carried out as follows. The value of the HOMO level was obtained by conversion of the value of the ionization potential measured with a photoelectron spectrometer (AC-2, produced by Riken Keiki Co., Ltd.) in the air into a negative value. The value of the LUMO level was obtained in such a manner that the absorption edge, which was obtained from Tauc plot with an assumption of direct transition using data on the absorption spectrum of the thin film, was regarded as an optical energy gap and was added to the value of the HOMO level. From the results of the measurement of electrochemical characteristics of the thin film, the HOMO level, the LUMO level, and the band gap (Bg) were found to be -5.84 eV, -2.78 eV, and 3.06 eV, respectively. The above results reveal that NPDBq has a relatively deep HOMO level, a relatively shallow LUMO level, and a relatively wide Bg. Electrochemical characteristics of an NPDBq solution were also measured. As a measuring... |
Tags: 1202564-31-5 synthesis path| 1202564-31-5 SDS| 1202564-31-5 COA| 1202564-31-5 purity| 1202564-31-5 application| 1202564-31-5 NMR| 1202564-31-5 COA| 1202564-31-5 structure
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H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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