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

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
pka9.07±0.10(Predicted)
color White to Off-White
InChIInChI=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
InChIKeyMSTZGVRUOMBULC-UHFFFAOYSA-N
SMILESC(C1=CC=C(O)C(N)=C1)(C1=CC=C(O)C(N)=C1)(C(F)(F)F)C(F)(F)F
CAS DataBase Reference83558-87-6(CAS DataBase Reference)
EPA Substance Registry SystemPhenol, 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
ProviderLanguage
SigmaAldrich English
2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane Usage And Synthesis
Description2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane (6FAP) 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.
Synthesis30 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 propertiesWhite powder
Uses2,2-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.
General Description2,2-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 materialsPhenol, 4,4'-[2,2,2-trifluoro-1-(trifluoromethyl)ethylidene]bis[2-nitro-
hexafluoro-2,2-diphenylpropane 4-CUMYLPHENOL 2,6-DINITRO-4-(2,2,2-TRIFLUORO-1-(4-HYDROXY-3-NITRO-PHENYL)-1-TRIFLUOROMETHYL-ETHYL)-PHENOL Hexafluoropropylene oxide 4,4'-(HEXAFLUOROISOPROPYLIDENE)-2,2'-DINITRO-DIPHENOL 3,4'-DIAMINODIPHENYLMETHANE ALTRENOGEST 1,1,1,2,3,3,3-Heptafluoropropane 3-Amino-6-morpholinopyridine Glycine Glycerol Hexafluorobisphenol A 2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane 2,2-Bis(3-amino-4-hydroxyphenyl)propane 1,1,1,3,3,3-Hexafluoropropane AMINO ACIDS 1,1,1,2,2,3-HEXAFLUOROPROPANE 3,3'-DIAMINODIPHENYLMETHANE

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