2,2′-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane

White powder

In a 10 mL reaction tube, a PTFE magnet is placed in a nitrogen atmosphere.Add 0.3 mmol of 5, 5'-(perfluoropropane-2, 2-diyl)bis(2-aminophenol), 2.4 mmol S8, 2.1 mmol 2-bromo-3, 3, 3-trifluoropropene, 0.9 mmol sodium bicarbonate, 0.2 mmol azobisisoheptanenitrile, 0.2 mmol of pinacol borate, 4.5 mL of N, N-dimethylformamideAfter stirring for 15 h in a 100 C closed system, it was extracted three times with ethyl acetate.The organic phase is combined, washed with a saturated sodium chloride solution and dried over anhydrous magnesium sulfate.The organic solvent was removed by rotary evaporation; the crude product obtained was obtained using n-pentane and ethyl acetate as eluent.Separated by silica gel column chromatography5, 5'-(Perfluoropropane-2, 2-diyl)bis(2-(2, 2, 2-trifluoroethyl)benzoxazole) (yield 80%).First, 18.3 g (0.05 mole) of 2, 2-bis(3-amino-4-hydroxyphenyl) hexafluoropropane (hereinafter referred to as BAHF) was dissolved in 100 mL of acetone and 17.4 g (0.3 mole) of propylene oxide, and cooled to -15 C. Then, a solution of 20.4 g (0.11 mole) of 3-nitrobenzoyl chloride dissolved in 100 mL of acetone was added dropwise. After the end of dropping, the solution was allowed to react at -15 C. for 4 hours, followed by allowing it to return to room temperature. The resulting white solid precipitate was separated out by filtration and vacuum dried at 50 C. A 30 g portion of the resulting white solid material was put in a 300 mL stainless steel autoclave and dispersed in 250 mL of methyl cellosolve, followed by adding 2 g of 5% palladium-carbon. Then, a balloon was used to introduce hydrogen to cause a reduction reaction at room temperature. About 2 hours later, the reaction was finished after checking that the balloon would deflate no more. After the end of the reaction, the solution was filtrated to remove the palladium compound used as catalyst and concentrated with a rotary evaporator to provide hydroxyl-containing diamine compound (alpha) as represented by the formula given below.18.31 g (0.05 mol) of BAHF, 17.4 g (0.3 mol) of propylene oxide and 100 mL of acetone were weighed in a three-necked flask and were dissolved. A solution prepared by dissolving 20.41 g (0.11 mol) of 3-nitrobenzoyl chloride in 10 mL of acetone was dropped thereto. After completion of the dropping, the mixture was allowed to react at -15 C. for 4 hours, and then the temperature was returned to room temperature. A precipitated white solid was filtered and vacuum dried at 50 C. The obtained solid of 30 g was placed in a 300 mL stainless steel autoclave and dispersed in 250 mL of 2-methoxyethanol, and 2 g of 5% palladium-carbon was added. Hydrogen was introduced here with a balloon and reacted at room temperature for 2 hours. Two hours later, the fact that the balloon no longer shrank was confirmed. After the termination of the reaction, a palladium compound as a catalyst was removed by filtration, followed by vacuum distillation and concentration, affording a hydroxy group-containing diamine compound (HFHA) having the following structure.General procedure: First, 10.9 g (0.1 mole) of 2-aminophenol was dissolved in 200 mL of tetrahydrofuran (THF) and 30.4 g (0.3 mole) of triethyl amine. Then, a solution of 19.1 g (0.1 mole) of decanoyl chloride dissolved in 100 mL of THF was added dropwise at a temperature of -10 C. or below. After the end of the dropwise addition, the reaction was continued at room temperature for 4 hours. Subsequently, a 1% hydrochloric acid solution was added, and the reaction solution was extracted with ethyl acetate to remove the solvent, followed by vacuum drying the resulting solid at 50 C. to provide an amido-phenol compound (b1-1) as represented by the formula given below.

2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane（BisAPAF） is a polyimide monomer.It is mairly used in the aynthesis of the heat resisting polymers,especially in the manufacture of specialty polymeoric electronic material-fluorinated polyimides.

Molecular Weight:366.26
XLogP3:3.8
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:2
Exact Mass:366.08029660
Monoisotopic Mass:366.08029660
Topological Polar Surface Area:92.5
Heavy Atom Count:25
Complexity:428
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes