2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane Chemical Properties

Melting point:

245-248 °C (lit.)

Boiling point:

411.3±45.0 °C(Predicted)

Density 

1.545±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

9.07±0.10(Predicted)

color 

White to Off-White

InChI

InChI=1S/C15H12F6N2O2/c16-14(17,18)13(15(19,20)21,7-1-3-11(24)9(22)5-7)8-2-4-12(25)10(23)6-8/h1-6,24-25H,22-23H2

InChIKey

MSTZGVRUOMBULC-UHFFFAOYSA-N

SMILES

C(C1=CC=C(O)C(N)=C1)(C1=CC=C(O)C(N)=C1)(C(F)(F)F)C(F)(F)F

CAS DataBase Reference

83558-87-6(CAS DataBase Reference)

EPA Substance Registry System

Phenol, 4,4'-[2,2,2-trifluoro-1-(trifluoromethyl)ethylidene]bis[2-amino- (83558-87-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29222990

MSDS

• Language:English Provider:SigmaAldrich

2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane Usage And Synthesis

Description

2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane (6FAP,83558-87-6) is white crystal. Its boiling point and density are expected to be 411.3±45.0 °C and 1.545±0.06 g/cm3, respectively. It is slightly soluble in DMSO and methanol.The product is non-toxic and can be stored at room temperature away from light and air.

Synthesis

30 g two (3-nitro-4-hydroxyphenyl) hexafluoropropanes are dropped into the 1000 mL autoclave, add 300 g DMF and 1.5 g palladium/carbon (the mass fraction of palladium in the palladium/carbon is 5%), press hydrogen to 1MPa, open stirring and be warmed up to 70 ℃, stop reaction after two (3-nitro-4-hydroxyphenyl) hexafluoropropane content＜0.1%, target product two (3-amino-4-hydroxyphenyl) hexafluoropropane Fluoropropane gas phase content is 98%, and the system is black, and the temperature of the still is lowered to room temperature, filtered, and the filtrate is de-dried under reduced pressure at 70-80°C to obtain bis(3-amino-4-hydroxyphenyl) hexafluoropropane crude product , the crude product is recrystallized, the recrystallization solvent is water and DMF, and the mass ratio of bis(3-amino-4-hydroxyphenyl)hexafluoropropane, water and DMF is 1:4:2.
First, the bis(3-nitro-4-hydroxyphenyl) hexafluoropropane crude product is mixed with the recrystallization solvent to increase the still temperature to 60 °C and stir, and then the still temperature is reduced to 10-20 °C for crystallization, filtered, After drying, 25.4 g of pure bis(3-nitro-4-hydroxyphenyl)hexafluoropropane was obtained. The yield of bis(3-amino-4-hydroxyphenyl)hexafluoropropane was 98.3% and the purity was 99.6%. 1H-NMR (400MHz, D6-DMSO) δ (ppm): 4.64 (s, 4H), 6.42 (d, 2H), 7.57 (s, 2H), 6.65 (d, 2H), 9.36 (s, 2H). 19F-NMR (400MHz, D6-DMSO) δ (ppm): -62.78. [1].

Physical properties

White powder

Uses

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.

Application

2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane (Bis-AP-AF/6FAP) consists of two aminophenols bridged with a hexafluoropropane. The reaction of Bis-AP-AF and BTDA can be used to synthesise polyimide (PI) films. The tensile strength, tensile modulus and elongation at break of the PI films were significantly improved by 60Co irradiation with an optimum irradiation dose of 50 kGy. The maximum increments in tensile strength, tensile modulus and elongation at break of the irradiated PI films were 37.8%, 45.0% and 95.2%, respectively. The high proton conductivity and good chemical and thermal stability of these fluorinated films make them most suitable for use in fuel cell systems. In addition, Bis-AP-AF can be used to synthesise polybenzoxazole (TR-PBO) membranes for use as semiconductor fabrication materials.

General Description

2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane, also referred to as 4,4′-(1,1,1,3,3,3-hexafluoro-2,2-propanediyl)bis(2-aminophenol), is an aromatic diamine.

2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane(83558-87-6)Related Product Information

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