2,4,6-TRIS(4-BROMOPHENYL)-1,3,5-TRIAZINE

(1) According to the literature [40], into the flask were quicklyadded dry CHCl3 (20 mL) and trifluoromethanesulfonic acid (6.0 g, 40 mmol). The solutionwas cooled down to 0 °C. Then, a solution of4-bromobenzonitrile (3.64 g, 20 mmol) in dry CHCl3 (120 mL) wasdropwise added to the pre-cooled solution. After the solution wasstirred for 0.5 h at 0 °C, the reaction systemwaswarmed up to roomtemperature and stirred for 24 h continuously. Afterwards, into thereaction mixture was added the aqueous ammonia solution (30percent)to neutralize the unreacted trifluoromethanesulfonic acid. After theaddition, the precipitate was formed. The precipitate was filtratedand washed with ethanol, hexane and chloroform to give 2, 4, 6-tris(4-bromophenyl)-1, 3, 5-triazine with the yield of 85percent as awhite powder. 1H NMR (300 MHz, CDCl3): d 8.61 (d, J 9 Hz 6H), 7.72 (d, J 9 Hz, 6H).In a 250 ml three-neck flask, chloroform (20 ml) was added, and trifluoromethanesulfonic acid (6.0 g, 40 mmol) was purged with nitrogen and cooled to0°C. Then, a solution of 4-bromobenzonitrile (3.64 g, 20 mmol) in chloroform was added dropwise thereto. The reaction was carried out at 0°C for half an hour, then the reaction was slowly warmed to room temperature and the reaction was continued for 24 hours. After the reaction was completed, an appropriate amount of aqueous ammonia solution was added thereto to neutralize the remaining trifluoromethanesulfonic acid. After the dropwise addition, a large amount of precipitate was formed. The precipitate was filtered and washed with ethanol, n-hexane and chloroform to obtain Compound 4 in a yield of 85percent.A 100-ml four-necked flask was charged with 0.01 mol of p-bromobenzene cyanide, 0.0363 mol of trifluoromethanesulfonic acid under a nitrogen atmosphere, and stirred at 0-5 ° C for 5 hours, then stirred at room temperature for 1 hour, and left at room temperature for 12 hours. , Add 50 ml of ice water, then add aqueous ammonium hydroxide solution.The pH was adjusted to 8-9, a large amount of precipitate was precipitated, suction filtration, and the cake was rinsed three times with distilled water to give a pale yellow solid.Recrystallization was carried out in a mixture of toluene:ethanol = 3:1, and filtered to obtain white crystals H1.The purity was 98.20percent, and the yield was 82.1percent.4-bromobenzonitrile (4 g, 22 mmol) in dry chloroform (60 mL) was added dropwise into a trifluoromethanesulfonic acid (4 mL, 44 mmol) in dry chloroform (10 mL) containing two necked round bottom flask with stirring at 0 °C under nitrogen gas protection. Heat was given out upon the addition of 4-bromobezonitrile. The reaction mixture was stirred for 2 hours at 0° C and continued to stir for 48 hours under ambient temperature and nitrogen gas protection. It was neutralized by adding small amount of ammonium hydroxide dropwise in water. The organic layer was washed with water for three times and then dried over anhydrous sodium sulphate. Solvent was removed in vacuo. The residual was recrystallized from CH3Cl to obtain a white powder 3.2 g in 80percent yield. 1H NMR (400MHz, CDCl3, δ): 8.55 (d, J = 8.5 Hz, 6H), 7.67 (d, J = 8.5 Hz, 6H). MS(MALDI-TOF, m/z): calcd. for C21H12Br3N3, 545.8634, found 545.8658 [M+H]+.8.3 g (68%) of Compound RET-1 was obtained according to the same method as the synthesis method of Chem. Lett., 33 10, 1244 2004. (0192) LC/MS calculated for: C39H27N3 Exact Mass: 537.2205 found for 538.22 [M+H]

Molecular Weight:546.1
XLogP3:7
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:544.85609
Monoisotopic Mass:542.85814
Topological Polar Surface Area:38.7
Heavy Atom Count:27
Complexity:377
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes