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- W4285676563 abstract "[1469704-61-7] C44H24ClN5 (MW 658.15) InChI = 1S/C44H24ClN5/c45-41-43(49-37-21-9-3-15-29(37)30-16-4-10-22-38(30)49)33(25-46)42(48-35-19-7-1-13-27(35)28-14-2-8-20-36(28)48)34(26-47)44(41)50-39-23-11-5-17-31(39)32-18-6-12-24-40(32)50/h1-24H InChIKey = AETFKBFYWGEUOV-UHFFFAOYSA-N (reagent used as a photocatalyst) Alternative Name: 2,4,6-tri(9H-carbazol-9-yl)-5-chloroisophthalonitrile. Physical Data: mp >300 °C. Solubility: Soluble in CH2Cl2 and THF and insoluble in H2O and hexanes. Form Supplied in: yellow solid. Analysis of Reagent Purity: The NMR and HRMS data reported for 3CzClIPN are as follows: 1H NMR (400 MHz, CDCl3): δ = 8.18–8.16 (m, 6H), 7.60–7.55 (m, 6H), 7.45–7.40 (m, 6H), 7.38–7.36 (m, 2H), 7.27–7.24 (m, 4H). 13C NMR (100 MHz, CDCl3): δ = 145.1, 144.2, 139.7, 139.2, 137.1, 126.92, 126.89, 124.8, 124.6, 122.4, 122.2, 121.3, 121.2, 117.6, 110.7, 109.5, 109.3. HR MS (ESI+, MeCN): m/z = 680.1630 [M + Na]+, calc. 680.1612.1 Preparative Methods: 3CzClIPN can be prepared from tetrachloroisophthalonitrile, carbazole, and NaH in THF.1 In a flame-dried Schlenk flask equipped with a magnetic stir bar, carbazole (836 mg, 5 mmol) was dissolved in dry THF (20 mL, 0.05 M, relating to 1.0 equiv of tetrachloroisophthalonitrile) under an atmosphere of nitrogen. Then, NaH (60% in mineral oil, 301 mg, 7.52 mmol) was added, and the suspension was stirred at room temperature for 30 min. Finally, 1.00 equiv of tetrachloroisophthalonitrile (266 mg, 1 mmol) was added, and the resulting mixture was stirred at room temperature for 24 h. The reaction mixture was quenched by the addition of water. After removal of THF, the residue was dissolved in DCM and washed with water. The organic phase was dried over Na2SO4 and the solvent was removed under reduced pressure to yield the crude product, which was purified by flash chromatography (hexanes/DCM, 12–81% DCM) to give 376 mg of 3CzClIPN as a yellow solid (57% yield). Handling, Storage, and Precautions: store in the dark. Keep away from strong reductants." @default.
- W4285676563 created "2022-07-17" @default.
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- W4285676563 date "2022-07-17" @default.
- W4285676563 modified "2023-10-18" @default.
- W4285676563 title "3CzClIPN" @default.
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- W4285676563 doi "https://doi.org/10.1002/047084289x.rn02470" @default.
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