83558-87-6

Basic information

• 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 NO: 83558-87-6
• Molecular Formula: C₁₅H₁₂F₆N₂O₂
• Molecular Weight: 366.26
• EINECS: 1308068-626-2
• Product Categories: fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis, functional materials;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, Organic Building Blocks
• Mol File: 83558-87-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 245-248 °C(lit.)
• Boiling Point: 411.3 °C at 760 mmHg
• Flash Point: 202.6 °C
• Appearance: Grey-white powders
• Density: 1.545 g/cm³
• Vapor Pressure: 2.36E-07mmHg at 25°C
• Refractive Index: 1.568
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.07±0.10(Predicted)
• CAS DataBase Reference: 2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane(83558-87-6)
• EPA Substance Registry System: 2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane(83558-87-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 83558-87-6(Hazardous Substances Data)

Usage

Description

2,2-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.

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.

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.

InChI:InChI=1/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

Upstream product

• 73340-33-7 2,2-bis(3-nitro-4-hydroxyphenyl)hexafluoropropane 
• 95-55-6 2-amino-phenol 
• 462-06-6 fluorobenzene 

Downstream Products

• 150649-78-8 2,2-bis(3-formylamino-4-hydroxyphenyl)hexafluoropropane 
• 1355021-31-6 2,2-bis(3-isocyano-4-tetrahydrofuranyloxyphenyl)hexafluoropropane 
• 1107-00-2 4,4'-(1,1,1,3,3,3-hexafluoroisopropylidene)diphthalic anhydride 
• 3016-76-0 1,1,1,3,3,3-hexafluoro-2,2-di(3,4-dicarboxyphenyl)-propane 
• 61005-79-6 2,2-bis(3,4-di-o-aminophenyl)hexafluoropropane 
• 618-95-1 methyl 3-nitrobenzoate 

Relevant articles and documents

Synthesis method of 2, 2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane

The invention discloses a synthesis method of 2, 2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane, which comprises the following steps: acetylating o-aminophenol serving as a starting material to obtain o-acetamidophenol, condensing the o-acetamidophenol with hexafluoroacetone trihydrate to obtain 2, 2-bis (3-acetamido-4-hydroxyphenyl) hexafluoropropane, and finally deacetylating to obtain the 2, 2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane. The synthetic route does not need catalytic hydrogenation or nitration, and compared with the existing route for synthesizing 2, 2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane, the synthetic route provided by the invention has the advantages of higher safety, more environmental friendliness, lower production cost and basically equivalent yield, thereby being more suitable for industrial mass production.

Synthesis method of 4, 4-(hexafluoroisopropenyl) diphthalic anhydride

The invention belongs to the technical field of synthesis of 4, 4-(hexafluoroisopropenyl) diphthalic anhydride, in particular to a synthesis method of 4, 4-(hexafluoroisopropenyl) diphthalic anhydride. The synthesis method has the advantages of easy separation of intermediate products, high yield, less waste and good economic benefit, and a mixed solvent of isobutanol and butyl acetate is adoptedto reduce the solubility of the product, facilitate the separation of the product and increase the yield. Besides, the Pd/C catalyst is pretreated, a proper amount of sulfide is added for pretreatment, the sulfur poisoning resistance of the catalyst is improved, the service life of the catalyst is prolonged, and the application frequency of the catalyst is increased; because nitro compounds contain trace amount of sulfides such as sulfuric acid and like, catalyst is easily poisoned. In the step 2, an alumina-silica gel catalyst is added so that 2, 2-bis (3-amino-4-hydroxyphenyl) molecules canbe adsorbed on the surface of the catalyst in a flat shape, hydroxyl is closer to the surface of the catalyst, and the amination reaction of hydroxyl is facilitated; in the step 4, a small amount of urea is added in the cyanolysis reaction to prevent diazonium salt from being oxidized, becoming tar and other side reactions.

Preparation process of 4, 4-(hexafluoroisopropenyl) diphthalic anhydride

The invention belongs to the technical field of synthesis of 4, 4-(hexafluoroisopropenyl) diphthalic anhydride, in particular to a preparation process of 4, 4-(hexafluoroisopropenyl) diphthalic anhydride. The preparation process has the advantages of easy separation of intermediate products, high yield, fewer wastes and favorable economic benefit, and adopts a mixed solvent of amyl alcohol and butyl acetate to lower the solubility of the product, thereby being beneficial to product separation and higher yield. Besides, the Pd/C catalyst is pretreated, a proper amount of sulfide is added for pretreatment, the sulfur poisoning resistance of the catalyst is improved, the service life of the catalyst is prolonged, and the application frequency of the catalyst is increased; because nitro compounds contain trace amount of sulfides such as sulfuric acid and like, catalyst is easily poisoned. In the step 2, an alumina-silica gel catalyst is added so that 2, 2-bis (3-amino-4-hydroxyphenyl) molecules can be adsorbed on the surface of the catalyst in a flat shape, hydroxyl is closer to the surface of the catalyst, and the amination reaction of hydroxyl is facilitated; in the step 4, a small amount of urea is added in the cyanolysis reaction to prevent diazonium salt from being oxidized, becoming tar and other side reactions.