3236-71-3

Basic information

• Product Name: 9,9-Bis(4-hydroxyphenyl)fluorene
• Synonyms: 9,9-BIS(4-HYDROXYPHENYL)FLUORENE;4,4'-(9-FLUORENYLIDENE)DIPHENOL;FLUORNEN-9-BISPHENOL;FLUORENE-9-BISPHENOL;LABOTEST-BB LT00112244;4,4’-(9h-fluoren-9-ylidene)bis-pheno;4-[9-(4-hydroxyphenyl)fluoren-9-yl]phenol;4,4'-(9-fluorenylidene)diphenol ,97%
• CAS NO: 3236-71-3
• Molecular Formula: C₂₅H₁₈O₂
• Molecular Weight: 350.41
• EINECS: 406-950-6
• Product Categories: Fluorene Derivatives;Fluorenes, Flurenones;Phenoles and thiophenoles;Electronic Chemicals;Color Former & Related Compounds;Developer;Fluorenes;Fluorenes & Fluorenones;Fluorenes, etc. (reagent for high-performance polymer research);Functional Materials;Reagent for High-Performance Polymer Research;Fluorene series
• Mol File: 3236-71-3.mol
• Article Data: 28

Chemical Properties

• Melting Point: 224-226 °C(lit.)
• Boiling Point: 526.4 °C at 760 mmHg
• Flash Point: 241 °C
• Appearance: white crystalline powder
• Density: 1.288 g/cm³
• Vapor Pressure: 1.07E-11mmHg at 25°C
• Refractive Index: 1.71
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.58±0.30(Predicted)
• Water Solubility: Insoluble in water
• BRN: 2060986
• CAS DataBase Reference: 9,9-Bis(4-hydroxyphenyl)fluorene(CAS DataBase Reference)
• NIST Chemistry Reference: 9,9-Bis(4-hydroxyphenyl)fluorene(3236-71-3)
• EPA Substance Registry System: 9,9-Bis(4-hydroxyphenyl)fluorene(3236-71-3)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36/38-50/53-36/37/38
• Safety Statements: 26-37-60-61-37/39
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 2
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 3236-71-3(Hazardous Substances Data)

Usage

The monomers and modifiers of functional polymer material

9,9-Bis(4-hydroxyphenyl)fluorene is the monomer and modifier of functional polymer material,it is Cardo skeleton structure bisphenol compound, it is important monomer and modifier of synthesis of fluorene-based epoxy resin, fluorene and benzene benzoxazine resins, acrylic resins, polyester resins, polycarbonate, epoxy, polyester or polyether condensation products. Fluorene-based epoxy resin has excellent humidity resistance and heat resistance, dielectric properties, mechanical properties, chemical resistance, etc., it has been important monomer and modifier of high-performance resin matrix materials, electronic packaging materials, high temperature resistant adhesives, heat resistant coatings, etc. But the rigidity of fluorene-based epoxy resin is better, but toughness is poor, therefore, it need to be modified toughening when be used, or use the method of mixing with general-purpose epoxy resin to modify. The above information is edited by the lookchem of Wang Xiaodong.

Uses

Different sources of media describe the Uses of 3236-71-3 differently. You can refer to the following data:
1. It can be used the intermediate of organic synthesis.
2. 9,9-Bis (4-Hydroxyphenyl) Fluorene is used in the production of polyarylene ethers and extensively used in the study of polymer electrolyte membranes with the potential for fuel cell application.
3. 4,4'-(9-fluorenylidene)diphenol be used for the synthesis of novel poly (arylene ether).
4. Bisphenol FL may be used as an analytical reference standard for the quantification of the analyte in: Human breast milk using gas chromatography-tandem mass spectrometry (GC-MS/MS). Wastewaters and surface water using gas chromatography-mass spectrometry (GC-MS).

Chemical Properties

White to tan powder or crystal or chunks

General Description

Bisphenol FL (BPFL) is a fluorinated derivative of bisphenol (BP), a wide group of chemicals with similar structures, recognized as environmental pollutants. Bisphenol A (BPA), and its structural analogs are widely used as plasticizers and monomers for synthetic materials, industrial and consumer products including fluorine rubber, food container linings, canned food, thermal receipts, etc.

InChI:InChI=1/C25H18O2/c26-19-13-9-17(10-14-19)25(18-11-15-20(27)16-12-18)23-7-3-1-5-21(23)22-6-2-4-8-24(22)25/h1-16,26-27H

Synthetic route

9,9-bis(4-methoxy-phenyl)-9H-fluorene (117766-40-2) → 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3)

Conditions	Yield
Stage #1: Fluorene-9,9-bisphenol dimethyl ether With boron tribromide In dichloromethane at 20℃; for 48h; Stage #2: at 20℃; under 12 Torr; for 4h; Further stages.;	98%

9-fluorenone (486-25-9) + phenol (108-95-2) → 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3)

Conditions	Yield
With hydrogenchloride In Zinc chloride; water; isopropyl alcohol	97%
With hydrogenchloride In Zinc chloride; water; isopropyl alcohol	97%
With sulfuric acid; 3-mercaptopropionic acid In dichloromethane at 20 - 40℃; for 6h;	92.5%

9-fluorenone (486-25-9) + phenol (108-95-2) → bis-(4-hydroxyphenyl)methane (620-92-8) + 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3)

Conditions	Yield
With hydrogenchloride In Zinc chloride; water; isopropyl alcohol	A n/a B 97%
In Zinc chloride; water; isopropyl alcohol	A 81% B n/a

9-fluorenone (486-25-9) → 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 60 percent / thioglycolic acid; aq. H2SO4 / acetic acid / 96 h / 20 °C 2.1: BBr3 / CH2Cl2 / 48 h / 20 °C 2.2: 98 percent / 4 h / 20 °C / 12 Torr View Scheme

methoxybenzene (100-66-3) + poly[styrene (iodoso diacetate)] → 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 60 percent / thioglycolic acid; aq. H2SO4 / acetic acid / 96 h / 20 °C 2.1: BBr3 / CH2Cl2 / 48 h / 20 °C 2.2: 98 percent / 4 h / 20 °C / 12 Torr View Scheme

9-fluorenone (486-25-9) + 3-mercaptopropionic acid (107-96-0) + phenol (108-95-2) → 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3)

Conditions	Yield
With hydrogenchloride

9-fluorenone (486-25-9) + phenol (108-95-2) → 9,9-bis(hydroxyphenyl)fluorene + 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3)

Conditions	Yield
With methanesulfonic acid at 140℃; for 24h; regioselective reaction;
With methanesulfonic acid at 140℃; for 3h; regioselective reaction;

9-fluorenone (486-25-9) + phenol (108-95-2) → 9-(4-hydroxyphenyl)-9(2-hydroxyphenyl)-fluorene (152480-63-2) + 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) + C44H30O3

Conditions	Yield
With n-butanethiol; N-propanesulfonic acid pyridinium hydrogen sulfate at 109.84℃; for 6h; Catalytic behavior; Reagent/catalyst; Time;

9-fluorenone (486-25-9) + phenol (108-95-2) → 9-(4-hydroxyphenyl)-9(2-hydroxyphenyl)-fluorene (152480-63-2) + 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3)

Conditions	Yield
With n-butanethiol; (3-sulfo)propyltriethylamine phosphate at 109.84℃; for 6h; Reagent/catalyst;

trifluoromethylsulfonic anhydride (358-23-6) + 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) → 9,9-bis[4-(trifluoromethylsulfonyloxy)phenyl]fluorene (218769-04-1)

Conditions	Yield
Stage #1: 9,9-bis(4-hydroxyphenyl)fluorene With pyridine In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at 0℃; Inert atmosphere;	98.4%
With pyridine at 0 - 20℃;	94%

9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) + 4-chlorobenzonitrile (100-00-5) → 9,9-bis-[4-(p-nitrophenoxy)phenyl]fluorene (139265-69-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; toluene at 100 - 150℃; for 3h;	96.2%
With potassium carbonate In N,N-dimethyl-formamide for 8h; Reflux;	94%

9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) + epichlorohydrin (106-89-8) → 9,9-bis[4-(2,3-epoxypropoxy)phenyl]fluorene

Conditions	Yield
Stage #1: 9,9-bis(4-hydroxyphenyl)fluorene With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.333333h; Inert atmosphere; Stage #2: epichlorohydrin In N,N-dimethyl-formamide; mineral oil at 20℃; for 162h;	96%
With potassium carbonate; N,N-dimethyl-formamide at 80℃; for 3h;	93.7%
With tetramethlyammonium chloride; sodium hydroxide In water; dimethyl sulfoxide; toluene at 40 - 100℃; for 1h; Inert atmosphere;	90%

9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) + 2-(2-chloro-5-nitrophenyl)-4,5-diphenyl-1H-imidazole (306745-14-2) → 9,9-bis{4-[2-(4,5-diphenylimidazol-2-yl)-4-nitrophenoxy]phenyl}fluorene (1423139-07-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide at 130℃; for 12h; Reflux;	96%

9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) + 3-Chloro-2-methylpropene (563-47-3) → 9,9-bis(4-methallyloxyphenyl)fluorene

Conditions	Yield
With potassium carbonate In acetone for 40h; Inert atmosphere; Reflux;	95.3%

BPA (80-05-7) + bis(p-fluorophenyl)sulfone (383-29-9) + 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) → polymer; monomer(s): 4-fluorophenyl sulfone; 9,9-bis(4-hydroxyphenyl)fluorene; 4,4\-isopropylidenediphenol

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide; toluene at 140 - 165℃; for 6h;	95%

9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) + subphthalocyanine (36530-06-0) → (B(N6C24H12))2O2C6H4C(C12H8)C6H4

Conditions	Yield
In 1,2-dichloro-benzene at 180.5℃; for 39h; Inert atmosphere;	95%
In 1,2-dichloro-benzene (Ar) chloro boron subphthalocyanine and bisphenol in 1,2-dichlorobenzenewere heated at reflux (180.5°C) for 39 h; react. mixt. was cooled, solvent was totary evapd., purification from hot toluene;	95%

9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) → C25H16O2(2-)*2Na(1+) (59507-02-7, 110299-21-3)

Conditions	Yield
With sodium hydroxide In acetone at 50℃; for 4h;	94%
With sodium hydroxide In dimethyl sulfoxide; toluene Heating; nitrogen atmosphere, azeotropic distillation;

bis-(4-nitro-3-trifluoromethyl-phenyl)-phenyl-amine (862095-62-3) + 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) → polymer, Mn 3.2E4 Da, PDI 1.8

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide; toluene at 140 - 180℃; for 15h;	93.3%

2-chloro-5-nitropyridine (4548-45-2) + 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) → C35H22N4O6

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide at 80℃; for 12h; Inert atmosphere;	93%

9,9-dimethyl-2,7-bis(chlorocarbonyl)fluorene (765314-37-2) + 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) → polymer; monomers: 9,9-dimethyl-2,7-bis(chlorocarbonyl)fluorene; 9,9-bis(4-hydroxyphenyl)fluorene

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane; water	92%

2,6 difluorobenzonitrile (1897-52-5) + 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) → C135H79F2N5O8

Conditions	Yield
Stage #1: 2,6 difluorobenzonitrile; 9,9-bis(4-hydroxyphenyl)fluorene With potassium carbonate In N,N-dimethyl acetamide; toluene at 140 - 165℃; for 5h; Inert atmosphere; Dean-Stark; Stage #2: 2,6 difluorobenzonitrile In N,N-dimethyl acetamide; toluene at 160℃; for 1h; Inert atmosphere; Dean-Stark;	92%

oxirane (75-21-8) + 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) → 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8)

Conditions	Yield
With potassium hydroxide In water; isopropyl alcohol at 30 - 65℃; for 6.83333h; Solvent; Temperature; Reagent/catalyst;	91.5%

formaldehyd (50-00-0) + 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) + dimethyl amine (124-40-3) → 2,5,2',5'-tetra(dimethylaminemethylene)-9,9-bis(4-hydroxyphenyl)fluorene (912474-64-7)

Conditions	Yield
In tetrahydrofuran at 50℃; for 24h;	91%
In ethanol; water for 3h; Mannich reaction; Heating;	57%

9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) + 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5) → C31H21O3P (1573113-23-1)

Conditions	Yield
With toluene-4-sulfonic acid at 140℃; for 12h;	90%

2-chloro-3-methyl-5-nitropyridine (22280-56-4) + 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) → C37H26N4O6

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide at 80℃; for 12h; Inert atmosphere;	90%

9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) + 4-nitrobenzonitrile (619-72-7) → C39H24N2O2

Conditions	Yield
Stage #1: 9,9-bis(4-hydroxyphenyl)fluorene With potassium hydroxide In N,N-dimethyl-formamide; toluene at 110℃; Stage #2: 4-nitrobenzonitrile In N,N-dimethyl-formamide; toluene at 100℃; for 3h;	88.3%

1-bromo-butane (109-65-9) + 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) → 9,9-bis(4-butoxyphenyl)-9H-fluorene

Conditions	Yield
Stage #1: 9,9-bis(4-hydroxyphenyl)fluorene With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 0.5h; Stage #2: 1-bromo-butane In N,N-dimethyl-formamide at 60℃; for 12h; Inert atmosphere;	88%

9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) + (2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluorononyl)oxirane (38565-53-6) → C47H28F34O4

Conditions	Yield
With dmap In ethanol for 12h; Reflux;	87%
With dmap In ethanol at 100℃; for 12h;

formaldehyd (50-00-0) + 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) + N-butylamine (109-73-9) → C37H40N2O2

Conditions	Yield
In 1,4-dioxane at 90℃; for 5h; Solvent; Temperature; Time;	86.3%

bis(p-fluorophenyl)sulfone (383-29-9) + 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) → polymer; monomer(s): 4-fluorophenyl sulfone; 9,9-bis(4-hydroxyphenyl)fluorene

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide; toluene at 140 - 165℃; for 6h;	86%

formaldehyd (50-00-0) + 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) + tert-butylamine (75-64-9) → C37H40N2O2

Conditions	Yield
In toluene at 100℃; for 1h; Solvent; Temperature; Time;	85.6%

9,9-bis(4-hydroxyphenyl)-9-silafluorene (956904-39-5) + 9,9-dimethyl-2,7-bis(chlorocarbonyl)fluorene (765314-37-2) + 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) → polymer; monomers: 9,9-dimethyl-2,7-bis(chlorocarbonyl)fluorene; 9,9-bis(4-hydroxyphenyl)-9-silafluorene, 40 spectr.%; 9,9-bis(4-hydroxyphenyl)fluorene, 60 spectr.%

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane; water	85%

9,9-bis(4-hydroxyphenyl)-9-silafluorene (956904-39-5) + 9,9-dimethyl-2,7-bis(chlorocarbonyl)fluorene (765314-37-2) + 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) → polymer; monomers: 9,9-dimethyl-2,7-bis(chlorocarbonyl)fluorene; 9,9-bis(4-hydroxyphenyl)-9-silafluorene, 65 spectr.%; 9,9-bis(4-hydroxyphenyl)fluorene, 35 spectr.%

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane; water	85%

4-fluorobenzoic acid ethyl ester (451-46-7) + 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) → 9,9'-bis-[(4-ethoxycarbonyl-phenyl)-oxyphenyl]-fluorene

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; potassium carbonate at 140℃; for 24h;	85%

(3-chloropropyl)-methyl-diisopropoxysilane (872864-91-0) + 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) → C45H62O6Si2 (919079-70-2)

Conditions	Yield
Stage #1: 9,9-bis(4-hydroxyphenyl)fluorene With potassium tert-butylate In N,N-dimethyl-formamide; isopropyl alcohol at 70℃; for 0.5h; Inert atmosphere; Stage #2: (3-chloropropyl)-methyl-diisopropoxysilane In N,N-dimethyl-formamide at 90 - 100℃; Inert atmosphere;	85%

Upstream product

• 117766-40-2 Fluorene-9,9-bisphenol dimethyl ether 
• 486-25-9 9-fluorenone 
• 108-95-2 phenol 
• 107-96-0 3-mercaptopropionic acid 
• 100-66-3 methoxybenzene 

Downstream Products

• 218769-04-1 9,9-bis[4-(trifluoromethylsulfonyloxy)phenyl]fluorene 
• 117344-32-8 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene 
• 59507-07-2 9,9-bis[4-(3,4-dicarboxyphenoxy)phenyl]fluorene 
• 59507-02-7 C₂₅H₁₆O₂^(2-)*2Na⁽¹⁺⁾ 
• 110299-21-3 Sodium; 4-[9-(4-hydroxy-phenyl)-9H-fluoren-9-yl]-phenolate 
• 1380543-27-0 9,9-bis(4-(trifluoromethyl)phenyl)-9H-fluorene 
• 1026380-15-3 9,9-bis[4-(4-nitro-3-hydroxylphenoxy)phenyl]fluorene 

Relevant articles and documents

Synthesis and characterization of fluorene-derived PU as a thermo cross-linked hole-transporting layer for PLED

Novel hole-transporting polyurethane, denoted as P1, resulting from the condensation of 9, 9-bis(4-hydroxyphenyl)fluorene and isophorone diisocyanate (denoted as IPDI) has been developed. When P1 is thermally consolidated in the presence of 2-(phosphonooxy)ethyl methacrylate (P2M), it forms a distinguished hole-transport layer that leads to an extremely good performance of the phosphorescent PLED. In the study, the device of ITO/PEDOT: PSS/P1-P2M/Ir(ppy) 3-t-PBD-PVK/Mg/Ag shows a high current efficiency of 27.6 cd/A and a low turn-on voltage of 6 V. In particular, the stable output efficiency of 17-22 cd/A within the range of 420-4400 cd/m2 at 12-20 V makes P1 a promising hole-transport material for phosphorescent PLED applications.

Bifunctional ionic liquid, preparation method thereof and application of bifunctional ionic liquid in catalytic synthesis of bisphenol compounds

The invention discloses a bifunctional ionic liquid, a preparation method thereof and application of the bifunctional ionic liquid in catalytic synthesis of bisphenol compounds, and belongs to the field of application of ionic liquid catalysts. The bifunctional ionic liquid is composed of heterocyclic quaternary ammonium cations containing sulfonic groups and sulfydryl and organic strong acid anions containing or not containing sulfydryl. The bifunctional ionic liquid has the functions of strong protonic acid and a -SH-containing compound, is used for catalytic synthesis of diphenolic acid, bisphenol A, bisphenol fluorene and the like, and has the characteristics of high reaction rate, high target product yield and good selectivity. The bifunctional ionic liquid is a green catalyst which is stable in performance and can be recycled, and compared with a protonic acid and sulfhydryl compound composite catalyst used in a traditional production process, the production process is simplified, equipment corrosion is reduced, and the production cost is reduced.

Blue light emitter based on fluorene unit (by machine translation)

The invention discloses a blue light emitter based on a fluorene unit. Due to the rigid planar biphenyl structure of the fluorene, materials are prone to intermolecular aggregation, so that the color purity, the efficiency and the stability of the material are greatly reduced. , The fluorene atom is taken as the core, different groups are introduced on 9No. positions to generate a series of fluorenyl derivatives, so that the solubility, the thermal stability, the photophysical property, the energy level and the carrier mobility are finely adjusted in a wide range. The present invention proposes a unique molecular framework (e.g. FTRTRZ) that helps achieve the most organised film and the highest carrier mobility, and the connection model that has been verified to be similar to FTRTRZ is a more viable approach to the production of efficient and stable blue emitters. (by machine translation)