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

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

Product Introduction

2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane Basic information
Description Synthesis
Product Name: 2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane
Synonyms: 1,1-Bis(3-aMino-4-hydroxyphenyl)-2,2,2-trifluoro-1-(trifluoroMethyl)ethane;2,2-Bis(3-aMino-4-hydroxylphenyl)hexafluoropropane(6FAP);2-aMino-4-[2-(3-aMino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol;4,4'-(Perfluoropropane-2,2-diyl)bis(2-aMinophenol);2,2-Bis(3-amino-4-hydroxyphenyl)hexafluopropane;2,2-Bis(3-amino-4-hydroxyphenyl)-hexafluoropropane(Bis-AP-AF/6FAP);BIS-AP-AF;4,4'-(HEXAFLUOROISOPROPYLIDENE)BIS(2-AMINOPHENOL)
CAS: 83558-87-6
MF: C15H12F6N2O2
MW: 366.26
EINECS: 617-475-0
Product Categories: fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis, Organic Building Blocks;Bisphenol AF type Compounds (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;Amino Alcohols;Organic Building Blocks;Oxygen Compounds;fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis, functional materials;83558-87-6
Mol File: 83558-87-6.mol
2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane Structure
 
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 Information
Provider Language
SigmaAldrich English
 
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].2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane
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 Preparation Products And Raw materials
Raw materials Phenol, 4,4'-[2,2,2-trifluoro-1-(trifluoromethyl)ethylidene]bis[2-nitro-

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