3096-56-8

Basic information

• Product Name: 2-Bromo-9-fluorenone
• Synonyms: 2-Bromo-9-fluorenone,95%;2-Bromofluorenone or 2-Bromo-9-fluorenone;9H-Fluoren-9-one,2-broMo-;2-broMo-9H-fluoren-9-one (2-BFone);2-BroMo-9H-fluorenone;2-BROMO-9-FLUORENONE;2-Bromo-9H-fluoren-9-one;2-Bromo-9-Fluorenone98%
• CAS NO: 3096-56-8
• Molecular Formula: C₁₃H₇BrO
• Molecular Weight: 259.1
• EINECS: 1806241-263-5
• Product Categories: Fluorene Series;organic chemicals and derivatives/others;OLED;OLED materials,pharm chemical,electronic;Fluorene Derivatives;Fluorenes, Flurenones;Electronic Chemicals;Fluorenes & Fluorenones;Fluorenones;C13 to C14;Carbonyl Compounds;Ketones
• Mol File: 3096-56-8.mol
• Article Data: 80

Chemical Properties

• Melting Point: 146-148 °C(lit.)
• Boiling Point: 392.8 °C at 760 mmHg
• Flash Point: 131.3 °C
• Appearance: yellow powder
• Density: 1.4633 (rough estimate)
• Vapor Pressure: 2.23E-06mmHg at 25°C
• Refractive Index: 1.5130 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Solubility in other solvents, soluble in acetone.
• CAS DataBase Reference: 2-Bromo-9-fluorenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-9-fluorenone(3096-56-8)
• EPA Substance Registry System: 2-Bromo-9-fluorenone(3096-56-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 3096-56-8(Hazardous Substances Data)

Usage

Description

2-Bromo-9-fluorenone is an organic intermediate characterized by its yellow powder form. It is a functional material known for its exceptional properties as a liquid crystal material, making it a valuable component in the development of advanced technologies.

Uses

Used in Organic Synthesis:
2-Bromo-9-fluorenone is used as an end-capping agent for poly(9,9-dialkylfluorene-2,7-diyl) derivatives, enhancing the performance and stability of these polymers in various applications.
Used in the Electronics Industry:
In the synthesis of 2-bromo-9-hydroxy-9-(2-biphenyl)fluorene, 2-Bromo-9-fluorenone serves as a crucial intermediate, contributing to the development of advanced electronic components and materials.
Used in the Production of Spirobifluorene Ligands:
2-Bromo-9-fluorenone is utilized in the preparation of spirobifluorene ligands, which are essential for the creation of sophisticated molecular structures with potential applications in various fields.
Used in the Synthesis of Altitudinal Molecular Motors:
This organic intermediate is employed in the synthesis of altitudinal molecular motors that contain functional groups in their rotor part, playing a vital role in the development of these innovative nanotechnological devices.
Used in the Synthesis of FB:
2-Bromo-9-fluorenone is also used in the synthesis of FB, a compound with potential applications in various industries, including pharmaceuticals and materials science.
Overall, 2-Bromo-9-fluorenone is a versatile and valuable compound with a wide range of applications across different industries, from organic synthesis to electronics and nanotechnology. Its unique properties as a liquid crystal material and an organic intermediate make it an essential component in the development of cutting-edge technologies and products.

Synthesis

The synthesis of 2-Bromo-9-fluorenone is as follows：the 9-fluorenone (10mmol), the phase transfer catalyst (1.5mmol fourteen alkyl trimethyl ammonium chloride) and brominated aqueous ammonium solution (30 wt %, 25mmol ammonium bromide) mixing and heating system temperature to 75 °C, in 1h is divided into three time 11mmol potassium bromate, to three times the weight ratio of 1:3:1, to maintain the system temperature to continue reaction 3h, wherein the 9-fluorenone, ammonium bromide, the molar ratio of potassium bromate 1 : 2.5: 1.1 ; 9-fluorenone, and fourteen alkyl trimethyl ammonium chloride (phase-transfer catalyst) molar ratio of 1 : 0.15; 2) after the reaction, to room temperature, by adding 20% aqueous solution of sodium sulfite ( eliminates the bromine fluid ), is filtered, the filter cake washing water And dried to obtain yellow solid of 2-Bromo-9-fluorenone, the yield is 99.2%.

Solubility in organics

2-Bromo-9-fluorenone was 0.0526 (mole fraction) in 1,4-dioxane at 323.15 K and 0.0002 (mole fraction) in methanol at 278.15 K, respectively, and the solubility increased with the increase in temperature in all solvents.

InChI:InChI=1/C13H7BrO/c14-8-5-6-10-9-3-1-2-4-11(9)13(15)12(10)7-8/h1-7H

Synthetic route

9-fluorenone (486-25-9) → 2-bromofluoren-9-one (3096-56-8)

Conditions	Yield
With potassium bromate; tetrabutyl-ammonium chloride; ammonium bromide In water at 75℃; for 6h; Temperature;	99.2%
With bromine In water at 80℃; for 4h; regioselective reaction;	94%
With bromine In water at 80 - 85℃; for 4.5h;	90.4%

2-bromo-9H-fluorene (1133-80-8) → 2-bromofluoren-9-one (3096-56-8)

Conditions	Yield
With air; caesium carbonate In dimethyl sulfoxide at 20℃; for 3h;	98%
With oxygen; potassium hydroxide In tetrahydrofuran at 20℃; for 14h;	98%
With air; graphene-supported KOH composite In N,N-dimethyl-formamide at 20℃; for 8h;	98%

2-bromo-9H-fluoren-9-ol (33417-29-7) → 2-bromofluoren-9-one (3096-56-8)

Conditions	Yield
With tert.-butylhydroperoxide In water at 100℃; for 24h;	98%
With N-Bromosuccinimide; potassium acetate In dichloromethane; water at 20℃; for 10h; Green chemistry;	98%
With picoline; tert.-butylhydroperoxide; chlorophyllin coppered trisodium salt In water; acetone at 80℃; for 10h; chemoselective reaction;	98%
With tert.-butylhydroperoxide; copper(II) acetate monohydrate In water at 80℃; for 8h;	92%
With 4-nitro-1-chlorobenzotriazole In water; acetic acid at 29.85℃; Kinetics;

4-bromo-[1,1′-biphenyl]-2-carboxylic acid (69200-18-6) → 2-bromofluoren-9-one (3096-56-8)

Conditions	Yield
Stage #1: 4-bromo-[1,1′-biphenyl]-2-carboxylic acid With thionyl chloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 8h; Stage #2: With aluminum (III) chloride at 20℃; for 6h;	91%
bei der Destillation;

m-bromobenzoic acid (585-76-2) + benzene (71-43-2) → 2-bromofluoren-9-one (3096-56-8)

Conditions	Yield
With sodium persulfate; (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid; trifluorormethanesulfonic acid; palladium diacetate In dimethyl sulfoxide at 80℃; for 24h; Schlenk technique;	79%

4'-bromo-[1,1'-biphenyl]-2-carbaldehyde (400747-91-3) → 2-bromofluoren-9-one (3096-56-8)

Conditions	Yield
With tert.-butylhydroperoxide; ferrocene In decane; acetonitrile at 20 - 90℃; for 24h;	76%
With carbon tetrabromide; oxygen In neat (no solvent) at 140℃;	51%

(3-bromophenyl)boronic acid (89598-96-9) + benzoyl chloride (98-88-4) → 2-bromofluoren-9-one (3096-56-8)

Conditions	Yield
With C31H25N2O3PPdS; potassium hydroxide In methanol; water at 50℃; for 6h; Catalytic behavior; Green chemistry; regioselective reaction;	71%

2,9-dibromo-9H-fluorene (6633-25-6) → 2-bromofluoren-9-one (3096-56-8) + 2,2'-dibromo-[9,9']bifluorenyl (95952-50-4)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; iron(II) oxalate dihydrate at 155 - 160℃; for 0.166667h;	A n/a B 70%

2-bromo-9H-fluorene (1133-80-8) + 2,4,6-triphenylpyrylium tetrafluoroborate (448-61-3) → 2-bromofluoren-9-one (3096-56-8)

Conditions	Yield
With oxygen In dichloromethane for 2h; Thermodynamic data; Irradiation;	65%
With oxygen In dichloromethane for 2h; Irradiation; Yield given;

4'-bromo-[1,1'-biphenyl]-2-carbonitrile (168072-17-1) → 2-bromofluoren-9-one (3096-56-8)

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); water; silver trifluoroacetate In N,N-dimethyl acetamide; trifluoroacetic acid at 140℃; for 72h; Heck Reaction; Glovebox; Inert atmosphere;	65%

5-bromo-2-iodobenzaldehyde (689291-89-2) + 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) → 2-bromofluoren-9-one (3096-56-8)

Conditions	Yield
With cesium fluoride; tris-(o-tolyl)phosphine; bis(dibenzylideneacetone)-palladium(0) In toluene; acetonitrile at 110℃; for 12h;	61%

9-fluorenone (486-25-9) → 2,7-dibromofluorene-9-one (14348-75-5) + 2-bromofluoren-9-one (3096-56-8)

Conditions	Yield
With bromine In water at 80℃; for 4h;	A n/a B 41%
With N-Bromosuccinimide; methanesulfonic acid In chloroform

2,7-dibromo-9H-fluorene (16433-88-8) → 2,7-dibromofluorene-9-one (14348-75-5) + 2-bromofluoren-9-one (3096-56-8)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide	A 31% B 23%

4'-bromo-[1,1'-biphenyl]-2-carboxylic acid (37174-65-5) → 2-bromofluoren-9-one (3096-56-8)

Conditions	Yield
With potassium carbonate; triphenylphosphine In 1,2-dichloro-ethane at 20℃; for 24h; Irradiation; Schlenk technique; Green chemistry;	30%

2-bromo-phenanthrene-9,10-dione (53622-33-6) → 2-bromofluoren-9-one (3096-56-8)

Conditions	Yield
With potassium hydroxide

2-bromo-phenanthrene-9,10-dione (53622-33-6) → 2-bromofluoren-9-one (3096-56-8) + 2-bromo-9-hydroxy-fluorene-9-carboxylic acid

Conditions	Yield
With potassium hydroxide at 80 - 90℃;

2,2'-dibromo-9,9'-dinitro-[9,9']bifluorenyl (857789-06-1) → 2-bromofluoren-9-one (3096-56-8)

2-bromo-9H-fluoren-9-ol (33417-29-7) + bromamine T (41085-71-6) → 2-bromofluoren-9-one (3096-56-8) + toluene-4-sulfonamide (70-55-3)

Conditions	Yield
With acetic acid for 24h;
With acetic acid at 30℃; Kinetics; Mechanism; Thermodynamic data; E(activ.), ΔH(activ.), ΔS(activ.), Γ(activ.);

2-Amino-3-brom-fluorenon (875488-46-3) → 2-bromofluoren-9-one (3096-56-8)

Conditions	Yield
(i) NaNO2, H2SO4, (ii) aq. H3PO2; Multistep reaction;

1-amino-7-bromo-9H-fluoren-9-one (16304-65-7) → 2-bromofluoren-9-one (3096-56-8)

Conditions	Yield
(i) NaNO2, aq. HCl, (ii) H3PO2; Multistep reaction;

7-Brom-fluorenon-(9)-carbonsaeure-(4) (16304-59-9) → 2-bromofluoren-9-one (3096-56-8)

Conditions	Yield
With quinoline; copper

9-fluorenone (486-25-9) + water (7732-18-5) + bromine (7726-95-6) → 2-bromofluoren-9-one (3096-56-8)

Conditions	Yield
at 100℃;

4'-bromo-diphenyl-carboxylic acid-(2)-chloride → 2-bromofluoren-9-one (3096-56-8)

Conditions	Yield
With aluminium trichloride

4-bromo-biphenyl-carboxylic acid-(2) → 2-bromofluoren-9-one (3096-56-8)

Conditions	Yield
With sulfuric acid at 50℃;

4-bromo-diphenyl-carboxylic acid-(2) → 2-bromofluoren-9-one (3096-56-8)

Conditions	Yield
bei der Destillation;

potassium-salt of (+-)-2-bromo-9-nitro-fluorene → 2-bromofluoren-9-one (3096-56-8)

Conditions	Yield
With air

2-bromo-9H-fluorene (1133-80-8) + acetic acid (64-19-7) + sodium dichromate → 2-bromofluoren-9-one (3096-56-8)

2-bromo-phenanthrene-9,10-dione (53622-33-6) + KOH-solution → 2-bromofluoren-9-one (3096-56-8) + 2-bromo-9-hydroxy-fluorene-9-carboxylic acid

Conditions	Yield
at 80 - 90℃;

2-bromo-9-aci-nitro-fluorene (857823-09-7) → 2-bromofluoren-9-one (3096-56-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol View Scheme

2-bromofluoren-9-one (3096-56-8) + phenylacetylene (536-74-3) → 2-phenylethynylfluorenone

Conditions	Yield
With copper(l) iodide; triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In N,N-dimethyl-formamide at 50℃; for 17h; Sonogashira reaction;	100%

2-bromofluoren-9-one (3096-56-8) + phenylmagnesium bromide (100-58-3) → 2-bromo-9-phenyl-9H-fluoren-9-ol (736928-22-6)

Conditions	Yield
In tetrahydrofuran at 0℃; for 0.333333h;	100%
In diethyl ether at 0℃; for 12h; Inert atmosphere;	95%
In tetrahydrofuran at 0 - 20℃; for 12h;	89%

2-bromofluoren-9-one (3096-56-8) + 2-(1-([1,1’-biphenyl]-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2-yl)-4,6-di-tert-butylphenol → C46H40N2O2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 6h; Reflux;	100%

2-bromofluoren-9-one (3096-56-8) → 2-hydroxyfluoren-9-one (6949-73-1)

Conditions	Yield
With lithium hydroxide monohydrate; N1-(4-hydroxy-2,6-dimethylphenyl)-N2-(4-hydroxy-3,5-dimethylphenyl)oxalamide; copper dichloride In water; dimethyl sulfoxide at 100℃; for 4h; Reagent/catalyst;	99.9%
With water; sodium hydroxide In ethanol at 90℃; for 6h; Temperature; Solvent;	83%
With tris(6,6'-diamino-2,2'-bipyridine); 4,4-diphenyl-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene; Br2Ni*3H2O; water; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile at 20℃; for 24h; Glovebox; Irradiation; Inert atmosphere;	71%

(1R,5S)-tert-butyl 3,6-diaza-bicyclo[3.2.0]heptane-6-carboxylate (799279-81-5) + 2-bromofluoren-9-one (3096-56-8) → 3-(9-oxo-9H-fluoren-2-yl)-(1S,5S)-3,6-diazabicyclo[3.2.0]heptane-6-carboxylic acid tert-butyl ester

Conditions	Yield
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); racemic-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl In toluene at 90℃; for 16h;	98%

2-bromofluoren-9-one (3096-56-8) + phenylboronic acid (98-80-6) → 2’-phenyl-9H-fluoren-9-one (3096-49-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 140℃; for 6h; Suzuki Coupling;	98%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 100℃; for 4h; Schlenk technique; Inert atmosphere; Sealed tube;	94%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 60℃; Reflux;	92%

2-bromofluoren-9-one (3096-56-8) + 2-bromo-3,3'-bipyridine (101002-03-3) → C23H15BrN2O

Conditions	Yield
Stage #1: 2-bromo-3,3'-bipyridine With n-butyllithium In tetrahydrofuran at -78℃; for 0.25h; Inert atmosphere; Stage #2: 2-bromofluoren-9-one In tetrahydrofuran at -78 - 20℃; for 4h;	98%

3-(2-bromophenyl)pyridine + 2-bromofluoren-9-one (3096-56-8) → C24H16BrNO

Conditions	Yield
Stage #1: 3-(2-bromophenyl)pyridine With n-butyllithium In tetrahydrofuran at -78℃; for 0.25h; Inert atmosphere; Stage #2: 2-bromofluoren-9-one In tetrahydrofuran at -78 - 20℃; for 4h;	98%

2-bromofluoren-9-one (3096-56-8) + 1-bromo-4-(2′-ethylhexyloxy)benzene (164352-24-3) → 2-bromo-9-(4-(2-ethylhexyloxy)phenyl)-fluoren-9-ol (916649-94-0)

Conditions	Yield
Stage #1: 1-bromo-4-(2′-ethylhexyloxy)benzene With iodine; magnesium In tetrahydrofuran Stage #2: 2-bromofluoren-9-one In tetrahydrofuran for 5h; Heating;	95%

2-bromofluoren-9-one (3096-56-8) → (2-bromo-9H-fluoren-9-ylidene)hydrazine (91805-38-8)

Conditions	Yield
With hydrazine hydrate In methanol for 3h; Heating;	95%
With hydrazine hydrate In methanol for 3h; Reflux; Inert atmosphere;	91%
With hydrazine hydrate In ethanol for 6h; Inert atmosphere; Reflux;

2-bromofluoren-9-one (3096-56-8) + 3,4,5-trimethoxyphenylboronic Acid (182163-96-8) → C22H18O4 (1050503-22-4)

Conditions	Yield
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In diethyl ether; ethanol at 110℃; for 0.166667h; Suzuki-Miyaura cross-coupling; microwave irradiation;	95%

2-bromofluoren-9-one (3096-56-8) + 2-(2-Bromophenyl)[1]benzofuran (129503-26-0) → C27H17BrO2

Conditions	Yield
Stage #1: 2-(2-Bromophenyl)[1]benzofuran With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 2-bromofluoren-9-one In tetrahydrofuran at 20℃; for 1h;	95%

2-bromofluoren-9-one (3096-56-8) + phenol (108-95-2) → 4,4'-(2-bromo-9H-fluorene-9,9-diyl)diphenol

Conditions	Yield
With methanesulfonic acid at 50℃; for 12h;	95%

2-bromofluoren-9-one (3096-56-8) → 2-bromo-7-nitro-9H-fluoren-9-one (58557-62-3)

Conditions	Yield
With sulfuric acid; nitric acid In water for 4h; Reflux; regioselective reaction;	93%
With sulfuric acid; nitric acid In water at 80 - 120℃; for 4.5h;	76.4%
With sulfuric acid; nitric acid In water at 80 - 85℃; for 4h;	76.4%

2-bromofluoren-9-one (3096-56-8) + 9H-carbazole (86-74-8) → C25H15NO

Conditions	Yield
With palladium diacetate; sodium t-butanolate; XPhos for 12h; Reflux; Inert atmosphere;	93%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 50 - 100℃; Inert atmosphere;	74%

2-bromofluoren-9-one (3096-56-8) → 2-bromo-9H-fluorene (1133-80-8)

Conditions	Yield
With palladium on activated charcoal; hydrogen; acetic acid at 60℃; for 7h;	93%

2-bromofluoren-9-one (3096-56-8) → 2-bromo-9H-fluoren-9-ol (33417-29-7)

Conditions	Yield
With sodium tetrahydroborate In methanol at 0 - 20℃;	91%
With sodium tetrahydroborate In methanol at 0 - 20℃;	91%
With sodium tetrahydroborate In isopropyl alcohol at 25 - 45℃; Kinetics;

2-Bromobiphenyl (2052-07-5) + 2-bromofluoren-9-one (3096-56-8) → 9-(biphenyl-2-yl)-2-bromo-9-fluorenol (236389-20-1)

Conditions	Yield
Stage #1: 2-Bromobiphenyl With magnesium; ethylene dibromide In diethyl ether at 50℃; for 3h; Grignard Reaction; Stage #2: 2-bromofluoren-9-one In diethyl ether at 20 - 50℃; for 27h; Stage #3: With water In diethyl ether at 20℃;	91%
Stage #1: 2-Bromobiphenyl With magnesium; ethylene dibromide In diethyl ether for 3h; Heating / reflux; Stage #2: 2-bromofluoren-9-one In diethyl ether for 2h; Heating / reflux; Stage #3: With water; ammonium chloride	90%
Stage #1: 2-Bromobiphenyl With magnesium In diethyl ether; ethylene dibromide for 3h; Inert atmosphere; Reflux; Stage #2: 2-bromofluoren-9-one In diethyl ether; ethylene dibromide for 14h; Inert atmosphere; Reflux;	90%

2-bromofluoren-9-one (3096-56-8) + C24H14BrNS → C37H22BrNOS

Conditions	Yield
Stage #1: C24H14BrNS With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Stage #2: 2-bromofluoren-9-one In tetrahydrofuran for 18h;	91%

2-bromofluoren-9-one (3096-56-8) → 2-bromo-9,9-dichlorofluorene (99515-75-0)

Conditions	Yield
With phosphorus pentachloride; trichlorophosphate at 80 - 90℃; for 24h; Reagent/catalyst; Solvent; Temperature; Green chemistry;	90.7%
With phosphorus pentachloride at 180℃;

2-bromofluoren-9-one (3096-56-8) + phenol (108-95-2) → 2-bromo-spiro[fluorene-9,9′-xanthene]

Conditions	Yield
In methanesulfonic acid at 152℃; for 24h; Inert atmosphere;	90%
With trichlorophosphate at 120℃;	87%
With trichlorophosphate at 120℃;	87%

2-bromofluoren-9-one (3096-56-8) → 9-(biphenyl-2-yl)-2-bromo-9-fluorenol (236389-20-1)

Conditions	Yield
Stage #1: 2-Bromobiphenyl With 1,1-Dibromoethane; magnesium In diethyl ether at 20℃; for 3.5h; Heating / reflux; Stage #2: 2-bromofluoren-9-one In diethyl ether at 20℃; Heating / reflux;	90%
Stage #1: 2-Bromobiphenyl With magnesium; ethylene dibromide In diethyl ether for 3h; Heating / reflux; Stage #2: 2-bromofluoren-9-one In diethyl ether at 20℃; for 14h; Heating / reflux; Stage #3: With water; ammonium chloride In diethyl ether	90%
Stage #1: 2-Bromobiphenyl With magnesium In tetrahydrofuran Stage #2: 2-bromofluoren-9-one In tetrahydrofuran at 20℃; for 14h; Heating / reflux; Stage #3: With water; ammonium chloride In tetrahydrofuran

2-bromofluoren-9-one (3096-56-8) → 2-bromo-7-iodo-9H-fluoren-9-one

Conditions	Yield
Stage #1: 2-bromofluoren-9-one With sulfuric acid; acetic acid In water at 60℃; for 1h; Stage #2: With iodine; periodic acid In water at 85℃; for 16h;	90%
Stage #1: 2-bromofluoren-9-one With sulfuric acid In water; acetic acid at 60℃; for 1h; Inert atmosphere; Stage #2: With iodine; periodic acid In water; acetic acid at 85℃; for 18h; Inert atmosphere; regioselective reaction;	89%

1,4-diethynylbenzene (935-14-8) + 2-bromofluoren-9-one (3096-56-8) → 1,4-bis((2-bromo-9-hydroxy-9H-fluorene-9-yl)ethynyl)benzene

Conditions	Yield
Stage #1: 1,4-diethynylbenzene With n-butyllithium In hexane at -10℃; for 1.5h; Inert atmosphere; Stage #2: 2-bromofluoren-9-one In hexane at -10 - 20℃; Inert atmosphere;	90%

2-bromofluoren-9-one (3096-56-8) + N-(2-bromophenyl)-N-phenylbenzenamine (78600-31-4) → (2'-bromo-10-phenyl-10H-spiro[acridine-9,9'-fluorene]) (1241891-64-4)

Conditions	Yield
Stage #1: N-(2-bromophenyl)-N-phenylbenzenamine With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 2-bromofluoren-9-one In tetrahydrofuran at -78 - 20℃;	90%
Stage #1: N-(2-bromophenyl)-N-phenylbenzenamine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: 2-bromofluoren-9-one In tetrahydrofuran; hexane for 3h; Stage #3: With hydrogenchloride In water; acetic acid for 6h; Reflux;	74.5%
Stage #1: 2-bromofluoren-9-one; N-(2-bromophenyl)-N-phenylbenzenamine With n-butyllithium In tetrahydrofuran at -78℃; for 4h; Inert atmosphere; Stage #2: With hydrogenchloride; acetic acid for 1h; Reflux; Inert atmosphere;	63%

2-bromofluoren-9-one (3096-56-8) → 2-bromo-9,9-difluorofluorene

Conditions	Yield
With (bis-(2-methoxyethyl)amino)sulfur trufluoride In ethanol for 48h;	90%
Multi-step reaction with 2 steps 1: trichlorophosphate; phosphorus pentachloride / 24 h / 80 - 90 °C / Green chemistry 2: iron(III) chloride; hydrogen fluoride / toluene / 24 h / 10 - 30 °C / Inert atmosphere View Scheme

Upstream product

• 1133-80-8 2-bromo-9H-fluorene 
• 448-61-3 2,4,6-triphenylpyrylium tetrafluoroborate 
• 486-25-9 9-fluorenone 
• 7732-18-5 water 
• 7726-95-6 bromine 
• 53622-33-6 2-bromo-phenanthrene-9,10-dione 
• 33417-29-7 2-bromo-9H-fluoren-9-ol 
• 689291-89-2 5-bromo-2-iodobenzaldehyde 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 400747-91-3 4'-bromo-[1,1'-biphenyl]-2-carbaldehyde 
• 589-87-7 1,4-bromoiodobenzene 
• 40138-16-7 2-formylbenzene boronic acid 
• 37174-65-5 4'-bromo-[1,1'-biphenyl]-2-carboxylic acid 
• 5794-88-7 5-Bromo-2-aminobenzoic acid 

Downstream Products

• 343233-87-4 2-bromo-9-(N-phenyl)-iminofluorene 
• 171408-76-7 2-bromo-9,9'-spirobifluorene 
• 736928-22-6 2-bromo-9-phenyl-9-hydroxyfluorene 
• 899422-06-1 2-bromo-spiro[fluorene-9,9′-xanthene] 
• 916649-94-0 2-bromo-9-(4-(2-ethylhexyloxy)phenyl)-fluoren-9-ol 
• 849222-39-5 C₁₃H₇OBrC₆H₆C₄H₈ 
• 75784-05-3 (2-Bromo-9-phenylamino-9H-fluoren-9-yl)-phosphonic acid 
• 75783-91-4 (2-Bromo-9-phenylamino-9H-fluoren-9-yl)-phosphonic acid diethyl ester 
• 1034472-28-0 9-(5,3'-bis(methoxy)biphenyl-2-yl)-2-bromofluoren-9-ol 
• 1050503-23-5 C₂₃H₁₆O₃ 
• 1050503-22-4 C₂₂H₁₈O₄ 
• 1029554-04-8 9,9-bis(4-diphenylaminophenyl)-2-bromofluorene 
• 23842-57-1 2-Brom-fluoren-9-on-oxim 
• 1356058-94-0 9-but-3-en-1-yl-2-(4-hydroxyphenyl)-9H-fluoren-9-ol 

Relevant articles and documents

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Molecular transmission: Controlling the twist sense of a helical polymer with a single light-driven molecular motor

Twisted sisters: Transmission of chirality from a light-driven rotary molecular motor to the macromolecular level of a polyisocyanate allows fully reversible control of the preferred helical sense of the polymer backbone (see picture). (Figure Presented).

Direct deoxygenative intramolecular acylation of biarylcarboxylic acids

A photocatalyzed intramolecular cyclization is developed for the synthesis of fluorenones. In this photoredox reaction, triphenylphosphine is used as an inexpensive and effective deoxygenative reagent for biarylcarboxylic acids to give acyl radicals, which quickly undergo intramolecular radical cyclization. Reactions in the presence of air and continuous flow photoredox technology demonstrate the generality and practicality of this process.

A solution processable fluorene-fluorenone oligomer with aggregation induced emission enhancement

Herein, we report a novel solution processable fluorenone based small molecule with an Aggregation Induced Emission Enhancement (AIEE) property. In contrast to previous reports, the presence of the fluorenone moiety in FF triggers the AIEE property.

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New highly fluorescent phthalocyanines dendrimers with fluorenyl-based connectors vs phenyl-based connectors

The design of dendrimers featuring conjugated fluorenyl dendrons via new connectors allows evaluating the importance of the role of these junctions and the nature of the core, on the optical properties of interest. In the continuation of our sustained interest for dendrimers and their use as luminescent labels for bioimaging, we wondered about the effect of changing the central porphyrin core for a phthalocyanine one in these macromolecular structures. Thus, a related phthalocyanine-based dendrimer possessing up to eight conjugated 9,9-dibutyl-2-fluorenyl endgroups was designed, and for the first time, these endgroups are linked to the central phthalocyanine core by new fluorenyl-based connectors C2 instead of the more classic 1,3,5-phenylene one C1. This original dendrimer was characterized and studied and as for porphyrin analogues, it was found that an efficient energy transfer occurs from the peripheral fluorenyl units to the central phthalocyanine core, leading to an intense red light emission. The luminescence is improved compared to that of their porphyrin-cored analogues for bioimaging, evidencing the key role played by the central core in this respect and the nature of the connector Cn. The impact of the structural changes of the core in relation with the impact resulting from the changes in dendron connectors is discussed.

Preparation method 2 -amino -9-9 - diphenyl fluorene

The invention discloses a preparation method of 2 - amino -9 and 9 - diphenyl fluorene, which comprises the following steps: taking 9 - fluorenone as a raw material, and carrying out bromination reaction to obtain 2 - bromo -9 - fluorenone. 2 - Bromo -9 - fluorenone and bromobenzene formative reagent are reacted to obtain 2 - bromo -9 - phenyl -9 - hydroxyl - fluorene. 2 - Bromo -9 - phenyl -9 - hydroxy - fluorene was subjected to an alkylation reaction with benzene to give 2 - bromo -9, 9 - diphenylfluorene. 2 - Bromo -9, 9 - diphenylfluorene and cuprous oxide, palladium acetate (II) and N - methylpyrrolidinone were reacted in liquid ammonia to give 2 - amino -9, 9 - diphenylfluorene. The preparation method is used for preparing 2 - amino -9 and 9 - diphenylfluorene, the used preparation is easy to obtain, the technological process is simple, the product yield is high, the production cost is reduced, 2 - amino -9 and 9 - diphenyl fluorene are produced.

Hole transport material and organic electroluminescent device containing same

The invention discloses a hole transport material and an organic electroluminescent device containing the same, and relates to the field of organic electroluminescent materials, wherein the structuralformula is shown in the specification. According to the invention, compared with a control example, the organic electroluminescent device prepared from the hole transport material has the advantagesthat the voltage is greatly reduced, and the light-emitting efficiency is remarkably improved, so that the compound provided by the invention can greatly reduce the driving voltage of the device, greatly reduces the consumption of electric energy, and remarkably improves the luminous efficiency; and by reducing the driving voltage, the service life of the organic electroluminescent device is remarkably prolonged.