117344-32-8

Basic information

• Product Name: Bisphenoxyethanolfluorene
• Synonyms: 9,9-BIS[4-(2-HYDROXYETHOXY)PHENYL]FLUORENE;4,4'-(9-FLUORENYLIDENE)BIS(2-PHENOXYETHANOL);Bisphenoxyethanolfluorene;bpef;LABOTEST-BB LT00112265;BISPHENOXY ETHANOL FLUORENONE;9,9-Bis[4-(2-Hydroxyethoxy)Phe;BISPHENOXYETHANOLFLUORENE 9,9-BIS[4-(2-HYDROXYETHOXY)PHENYL]FLUORENE
• CAS NO: 117344-32-8
• Molecular Formula: C₂₉H₂₆O₄
• Molecular Weight: 438.51
• EINECS: 1806241-263-5
• Product Categories: Fluorenes;Fluorenes & Fluorenones;Fluorenes, etc. (reagent for high-performance polymer research);Functional Materials;Reagent for High-Performance Polymer Research;Fluorene series;Alcohols;C9 to C30;Oxygen Compounds;Pharmaceutical intermediates;Fine chemical
• Mol File: 117344-32-8.mol
• Article Data: 16

Chemical Properties

• Melting Point: 117-120 °C(lit.)
• Boiling Point: 610.7 °C at 760 mmHg
• Flash Point: 323.1 °C
• Appearance: /
• Density: 1.248 g/cm³
• Storage Temp.: 2-8°C
• PKA: 13.95±0.10(Predicted)
• Water Solubility: Insoluble in water
• CAS DataBase Reference: Bisphenoxyethanolfluorene(CAS DataBase Reference)
• NIST Chemistry Reference: Bisphenoxyethanolfluorene(117344-32-8)
• EPA Substance Registry System: Bisphenoxyethanolfluorene(117344-32-8)

Safety Data

• Hazard Codes: Xi
• Statements: 37
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 117344-32-8(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

4,4′-(9-Fluorenylidene)bis(2-phenoxyethanol) may be used for the following syntheses:poly-(carbotetramethyldisiloxane)s, containing poly[oxy{4,4′-(9-fluorenylidene)bis(2-phenoxyethylene)}oxytetramethyldisiloxane] (a fluorescent aromatic chromophore group)poly[oxy(arylene)oxy(tetramethyldisilylene)]s, containing fluorescent aromatic chromophore groups in the polymer main chain, via melt copolymerization reaction with 1,2-bis(diethylamino)tetramethyldisilane

General Description

4,4′-(9-Fluorenylidene)bis(2-phenoxyethanol) is an aryldiol.

Synthetic route

2-Phenoxyethanol (122-99-6) + 9-fluorenone (486-25-9) → 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8)

Conditions	Yield
With sulfuric acid; ethanethiol for 12h; Reagent/catalyst; Reflux;	94.5%
With 3-mercaptopropionic acid In chlorobenzene at 115℃; for 2h; Solvent; Temperature; Reagent/catalyst;	92.5%
tungstophosphoric acid In toluene at 130℃; under 15.0015 Torr; for 4h; Product distribution / selectivity; Inert atmosphere;	90.2%

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%

[1,3]-dioxolan-2-one (96-49-1) + 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) → 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8)

Conditions	Yield
With potassium fluoride In N,N-dimethyl-formamide for 4h; Inert atmosphere; Reflux;	75%
With potassium fluoride In N,N-dimethyl-formamide for 4h; Inert atmosphere; Reflux;	75%

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

Conditions	Yield
anion exchange resin A (Cl-type) In 2-methoxy-ethanol at 100℃; for 12h;	A 2.0 %Chromat. B 98.0 %Chromat.

phenoxyethyl alcohol (56101-99-6) + 9-fluorenone (486-25-9) + phenol (108-95-2) → 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8)

9-fluorenone (486-25-9) → 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 3-mercaptopropionic acid; methanesulfonic acid / toluene / 13 h / 40 °C / Inert atmosphere 2: potassium fluoride / N,N-dimethyl-formamide / 4 h / Inert atmosphere; Reflux View Scheme

phenol (108-95-2) → 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 3-mercaptopropionic acid; methanesulfonic acid / toluene / 13 h / 40 °C / Inert atmosphere 2: potassium fluoride / N,N-dimethyl-formamide / 4 h / Inert atmosphere; Reflux View Scheme

2-Phenoxyethanol (122-99-6) + 9,9-dichloro-9H-fluorene (25023-01-2) → 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8)

Conditions	Yield
Stage #1: 2-Phenoxyethanol; 9,9-dichloro-9H-fluorene at 70℃; for 3h; Inert atmosphere; Stage #2: With methanesulfonic acid at 110℃; for 9h; Inert atmosphere;	13.5 g

epichlorohydrin (106-89-8) + 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8) → 9,9-bis[4-(2,3-epoxypropoxyethoxy)phenyl]fluorene

Conditions	Yield
With calcium chloride; sodium hydroxide at 65℃; Green chemistry;	98.8%
With N-benzyl-N,N,N-triethylammonium chloride at 60℃; for 1h;
With N-benzyl-N,N,N-triethylammonium chloride at 60℃; for 1h;

3-mercaptobutyric acid (26473-49-4) + 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8) → 9,9-bis{4-(3-mercaptobutyloyloxyethoxy)phenyl}fluorene

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 140℃; for 3h;	97.1%

9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8) → C29H24Cl2O2

Conditions	Yield
With pyridine; thionyl chloride In tetrahydrofuran at 60℃; for 4h; Inert atmosphere;	95%
With pyridine; thionyl chloride In tetrahydrofuran at 60℃; for 4h; Inert atmosphere;	95%
With pyridine; thionyl chloride In tetrahydrofuran at 60℃; for 4h; Inert atmosphere;	95%

p-toluenesulfonyl chloride (98-59-9) + 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8) → C43H38O8S2 (1203647-68-0)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 120h;	93%

1,4-diisocyanatobenzene (104-49-4) + 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8) + 2-hydroxyethyl acrylate (818-61-1) → C55H50N4O14

Conditions	Yield
Stage #1: 1,4-diisocyanatobenzene; 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene With dibutyltin(II) dilaurate; 4-methoxy-phenol In toluene at 40 - 95℃; for 3h; Inert atmosphere; Stage #2: 2-hydroxyethyl acrylate In toluene at 40 - 95℃; for 2h; Inert atmosphere;	88%

9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8) + 2-mercapto-2-methylpropanoic acid (4695-31-2) → 9,9-bis{4-(2-mercaptoisobutyloyloxyethoxy)phenyl}fluorene

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 140℃; for 4h;	86.8%

acryloyl chloride (814-68-6) + 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8) → 9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene

Conditions	Yield
With triethylamine In acetone at 0 - 20℃; for 6.5h;	83.6%

D-glucose (50-99-7) + 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8) → 9-[4-(2-hydroxyethoxy)phenyl]-9-[4-(2-glucosyloxyethoxy)phenyl]fluorene + 9-[4-(2-hydroxyethoxy)phenyl]-9-{4-[2-(2-formyl-5-furylmethoxy)ethoxy]phenyl}fluorene + 9-[4-(2-hydroxyethoxy)phenyl]-9-{4-[2-(4-oxopentanoyloxy)ethoxy]phenyl}fluorene

Conditions	Yield
With sulfuric acid at 200℃; for 1h; Temperature; Reagent/catalyst;	A 0.7% B n/a C 73.6%

acrylic acid (79-10-7) + 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8) → 9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene

Conditions	Yield
With methanesulfonic acid In benzene for 12h; Inert atmosphere; Reflux; Dean-Stark;	65%
With methanesulfonic acid In benzene for 12h; Dean-Stark; Inert atmosphere; Reflux;	65%
With toluene-4-sulfonic acid; 4-methoxy-phenol In toluene at 110 - 115℃;	258.8 g

9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8) + poly(ethylene terephthalate), Mn 31 kg/mol, Mw 72 kg/mol, PDI 2.3; monomer(s): bis(2-hydroxyethyl) terephthalate → polymer, Mn 29 kg/mol, Mw 68 kg/mol, PDI 2.3, fluorene units content 10 percent; monomer(s): bis(2-hydroxyethyl) terephthalate; 4,4\-(9-fluorenylidene)bis(2-phenoxyethanol)

Conditions	Yield
With antimony(III) trioxide at 20 - 210℃; under 0.045004 Torr; for 25.5h;

9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8) → C67H50O6 (1203647-70-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / tetrahydrofuran / 120 h / 0 - 20 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 80 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 1.67 h / -78 °C 3.2: -78 - 20 °C View Scheme

9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8) → C41H32Br2O4 (1203647-69-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 120 h / 0 - 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 80 °C View Scheme

9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8) + acetylene (74-86-2) → 9,9-bis(4-(2-(vinyloxy)ethoxy)phenyl)-9H-fluorene

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 100℃; under 300.03 Torr; for 6h; Inert atmosphere;

acryloyl chloride (814-68-6) + 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8) + Methacryloyl chloride (920-46-7) → C36H32O6

Conditions	Yield
Stage #1: acryloyl chloride; 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene With triethylamine In tetrahydrofuran at 20℃; for 3h; Cooling with ice; Stage #2: Methacryloyl chloride In tetrahydrofuran at 20℃; for 12h;

coniferol (458-35-5) + 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8) → C39H36O6 + C49H50O9

Conditions	Yield
In 1,4-dioxane at 180℃; for 0.5h;

2-Isocyanatoethyl methacrylate (30674-80-7) + 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8) → (((((((9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(carbonyl))bis(azanediyl))bis(ethane-2,1-diyl) bis(2-methylacrylate)

Conditions	Yield
With stannous octoate In ethyl acetate at 60℃; for 16h;

acrylic acid 2-isocyanatoethyl ester (13641-96-8) + 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8) → (((((((9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(carbonyl))bis(azanediyl))bis(ethane-2,1-diyl) diacrylate

Conditions	Yield
With stannous octoate In ethyl acetate at 60℃; for 16h;

3-(trimethoxysilyl)propyl isocyanate (15396-00-6) + 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (117344-32-8) → C36H41NO8Si

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In tetrahydrofuran for 6h; Reflux;

Upstream product

• 122-99-6 2-Phenoxyethanol 
• 25023-01-2 9,9-dichloro-9H-fluorene 
• 108-95-2 phenol 
• 96-49-1 [1,3]-dioxolan-2-one 
• 3236-71-3 9,9-bis(4-hydroxyphenyl)fluorene 
• 486-25-9 9-fluorenone 
• 75-21-8 oxirane 
• 56101-99-6 phenoxyethyl alcohol 

Downstream Products

• 161182-73-6 9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene 
• 259881-39-5 9,9-bis[4-(2,3-epoxypropoxyethoxy)phenyl]fluorene 
• 1203647-69-1 C₄₁H₃₂Br₂O₄ 
• 1203647-68-0 C₄₃H₃₈O₈S₂ 

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Synthesis of fluorenebisphenoxy derivatives by acid-sulfur compound catalyzed condensation reaction

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9,9-BIS(4-(2-HYDROXYETHOXY)PHENYL)FLUORENE CRYSTAL

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