1,6,7,12-tetrachloroperylene Tetracarb...

A mixture of 3, 4, 9, 10-perylenetetracarboxylic dianhydride(3.30 g, 8.41 mmol), chlorosulfonic acid (20 mL, 300 mmol) andiodine (0.56 g, 2.20 mmol) was stirred at 65 C for 30 h. Aftercooling to room temperature, the solution was added dropwise toan ice-water mixture. The precipitate was collected by filtration togive a red solid (4.14 g, 92percent). 1H NMR (d-DMSO, ppm): 8.75 (s, 4H, aromatic protons). 13C NMR (d-DMSO, ppm): 119.75, 125.29, 129.5, 134.88, 136.22, 158.16, 168.53. Mass (EI): m/z 532.10253] (Compound (Id) Manufacturing Process)10254] Chlorosulfuric acid (500 g, 4.29 mol) was inserted into a 1000 ml three neck flask under an argon gas flow. 3, 4, 9, 10-perylene tetracarboxylic acid dianhydride (50 g, 0.127 mol) was added to the chlorosulfuric acid for 20 minutes at the room temperature and then iodine (8.5 g, 0.024 mol) was added. 10255] Then, the temperature of the reaction liquid was increased up to 70° C., and reaction was performed with stirring for 6 hours.10256] After the reaction was completed, the reaction liquidwas cooled such that the temperature became the room temperature, and quenching was performed with cool water(2000 ml). The reaction liquid was discolored from dark brown to scarlet and crystals were precipitated. These crystals were taken out, and subjected to slurry washing with water (1000 ml) three times. Then, slurry washing was performed three times with acetonitrile (500 ml), and taken crystals were dried. Thus, a compound (abbreviated to a “compound (1)- bid”) which was represented by the following formula (1)- bid, as the compound (Id) was obtained (collected amount:50.1 g, and yield: 74.4percent).10257] It was confirmed that the compound (1)-bid was obtained, by MS measurement, ion chromatography, and IR measurement. For example, a spectrum of a pro-ion peak mlz=530 was confirmed in the MS measurement. It was confirmed that a chlorine content was 25.1percent (ideal value: 26.8percent) by using an oxygen combustion method in the ion chromatography.First, a reaction represented by the reaction formula (1-11) was performed as a reaction process 1.500 g of chlorosulthric acid (4.29 mol) was added to 1000 mE of a three-necked flask through argon gas, and 50 g (0.127mol) of 3, 4, 9, 10-perylenetetracarboxylic acid dianhydridewas added thereto at room temperature for 20 minutes. Next, 8.5 g (0.024 mol) of iodine was added thereto. The tempera- tare of the obtained reaction liquid was increased to 70° C., and the reaction liquid was reacted by stirring for 6 hours.After the reaction was terminated, the temperature of the reaction liquid was cooled to the room temperature, 2000 mE of ice water was added thereto, and then the reaction liquid was quenched. The color of the reaction liquid was changed from dark brown into vermilion and crystals were deposited. The crystals were collected by filtration to be slurry-washed using 1000 mE of water for three times. Subsequently, slurry washing was thrther performed using 500 mE of acetonitrile for three times. The collected crystals by filtration were dried. The wet weight of an obtained product was 102 g, the dry 25 weight thereof was 50.1 g, and the yield thereof was 74.4percent.In a 100 ml three-necked flask equipped with a reflux condenser and two glass stoppers 3, 4:9, 10-perylene tetracarboxylic dianhydride (1 g, 2.55 mmol) and iodine (170 mg, 0.67 mmol) were dissolved in chlorosulfonic acid (10 ml). The mixture was heated to 70 °C for 5 h. Afterwards the reaction mixture was poured into an ice-water mixture and the insoluble product was collected by filtration. The crude product was purified by soxhlet extraction using dichloromethane as solvent. The solvent was evaporated by the rotary evaporator to yield a red solid. Yield 2.3 g (62.2percent) IR (ν(cm

Molecular Weight:530.1
XLogP3:7
Hydrogen Bond Acceptor Count:6
Exact Mass:529.873248
Monoisotopic Mass:527.876199
Topological Polar Surface Area:86.7
Heavy Atom Count:34
Complexity:854
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes