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4-Bromo-9H-fluoren-9-one, also known as 4-bromo-9-fluorenone, is an organic compound characterized by the molecular formula C13H7BrO. It presents as a pale yellow solid and is recognized for its utility as an intermediate in the synthesis of pharmaceuticals and agrochemicals. 4-Bromo-9H-fluoren-9-one is also employed as a building block in the creation of advanced materials. Its chemical properties, including the capacity to participate in halogenation, oxidation, and condensation reactions, render it a versatile entity in the realm of organic chemistry. Furthermore, 4-Bromo-9H-fluoren-9-one serves as a significant research tool, facilitating the exploration of structure-activity relationships in organic compounds and the advancement of novel synthetic methodologies.

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  • 4269-17-4 Structure
  • Basic information

    1. Product Name: 4-Bromo-9H-fluoren-9-one
    2. Synonyms: NSC81339;4-broMo-9H-fluoren-9-one;4-Bromofluorenone;4-BroMo-9-fluorenone;4-Bromo-fluoren-9-one;9H-Fluoren-9-one, 4-bromo-;4-Bromo-9H-fluoren-9-one
    3. CAS NO:4269-17-4
    4. Molecular Formula: C13H7BrO
    5. Molecular Weight: 259.09808
    6. EINECS: N/A
    7. Product Categories: OLED
    8. Mol File: 4269-17-4.mol
  • Chemical Properties

    1. Melting Point: 127.0 to 131.0 °C
    2. Boiling Point: 392.8°Cat760mmHg
    3. Flash Point: 131.3°C
    4. Appearance: /
    5. Density: 1.609
    6. Vapor Pressure: 2.23E-06mmHg at 25°C
    7. Refractive Index: 1.691
    8. Storage Temp.: Sealed in dry,Room Temperature
    9. Solubility: N/A
    10. CAS DataBase Reference: 4-Bromo-9H-fluoren-9-one(CAS DataBase Reference)
    11. NIST Chemistry Reference: 4-Bromo-9H-fluoren-9-one(4269-17-4)
    12. EPA Substance Registry System: 4-Bromo-9H-fluoren-9-one(4269-17-4)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 4269-17-4(Hazardous Substances Data)

4269-17-4 Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
4-Bromo-9H-fluoren-9-one is utilized as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides. Its role in these industries is pivotal for the creation of effective and novel compounds with potential therapeutic and agricultural applications.
Used in Advanced Material Production:
As a building block, 4-Bromo-9H-fluoren-9-one is employed in the production of advanced materials, where its chemical properties allow for the engineering of materials with specific characteristics required for high-performance applications.
Used in Organic Chemistry Research:
4-Bromo-9H-fluoren-9-one serves as a valuable research tool in organic chemistry, enabling scientists to study structure-activity relationships in organic compounds. This understanding is crucial for the design and development of new synthetic methodologies and the optimization of existing chemical processes.
Used in the Development of New Synthetic Methodologies:
4-Bromo-9H-fluoren-9-one is instrumental in the advancement of new synthetic methodologies, providing a platform for chemists to explore innovative approaches to organic synthesis, potentially leading to more efficient and environmentally friendly chemical processes.

Check Digit Verification of cas no

The CAS Registry Mumber 4269-17-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,2,6 and 9 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 4269-17:
(6*4)+(5*2)+(4*6)+(3*9)+(2*1)+(1*7)=94
94 % 10 = 4
So 4269-17-4 is a valid CAS Registry Number.
InChI:InChI=1/C13H7BrO/c14-11-7-3-6-10-12(11)8-4-1-2-5-9(8)13(10)15/h1-7H

4269-17-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-bromofluoren-9-one

1.2 Other means of identification

Product number -
Other names 4-bromofluorenone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4269-17-4 SDS

4269-17-4Synthetic route

bromobenzene
108-86-1

bromobenzene

3-Bromopropionyl chloride
15486-96-1

3-Bromopropionyl chloride

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

Conditions
ConditionsYield
Stage #1: bromobenzene In dichloromethane at 5℃; for 0.5h;
Stage #2: 3-Bromopropionyl chloride In dichloromethane at 5 - 20℃; for 16h;
Stage #3: With trifluorormethanesulfonic acid In dichloromethane at 90℃; for 4h; Temperature; Reagent/catalyst;
88.5%
2'-bromo-[1,1'-biphenyl]-2-carbonitrile
54245-41-9

2'-bromo-[1,1'-biphenyl]-2-carbonitrile

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

Conditions
ConditionsYield
With sulfuric acid; acetic acid for 12h; Reflux;80%
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;57%
With sulfuric acid
ethyl 2’-bromo-[1,1’-biphenyl]-2-carboxylate
690260-87-8

ethyl 2’-bromo-[1,1’-biphenyl]-2-carboxylate

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

Conditions
ConditionsYield
With methanesulfonic acid at 100℃; for 14h;61%
9-fluorenone
486-25-9

9-fluorenone

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

Conditions
ConditionsYield
With N-Bromosuccinimide; sulfuric acid In dichloromethane at 20℃; for 12h;47.9%
1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

(S)-2-(3-bromo-2-iodophenyl)-4-isopropyl-4,5-dihydrooxazole

(S)-2-(3-bromo-2-iodophenyl)-4-isopropyl-4,5-dihydrooxazole

A

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

B

(4S)-2-(6-bromo-2'-iodo-(1,1'-biphenyl)-2-yl)-4-isopropyl-4,5-dihydrooxazole

(4S)-2-(6-bromo-2'-iodo-(1,1'-biphenyl)-2-yl)-4-isopropyl-4,5-dihydrooxazole

Conditions
ConditionsYield
Stage #1: (S)-2-(3-bromo-2-iodophenyl)-4-isopropyl-4,5-dihydrooxazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Inert atmosphere;
Stage #2: 1-Bromo-2-iodobenzene In tetrahydrofuran; hexane at -78℃; Inert atmosphere;
Stage #3: With n-butyllithium In tetrahydrofuran; hexane at -78 - 25℃; for 12h; Inert atmosphere; diastereoselective reaction;
A 20%
B 46%
Stage #1: (S)-2-(3-bromo-2-iodophenyl)-4-isopropyl-4,5-dihydrooxazole With n-butyllithium In tetrahydrofuran; hexane at -78℃;
Stage #2: 1-Bromo-2-iodobenzene In tetrahydrofuran; hexane at -78℃; for 12h; Overall yield = 46 %; Overall yield = 234 mg; diastereoselective reaction;
A n/a
B n/a
furfural
98-01-1

furfural

2-bromo-2’-iodo-1,1’-biphenyl
39655-12-4

2-bromo-2’-iodo-1,1’-biphenyl

A

9-fluorenone
486-25-9

9-fluorenone

B

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 1,3-bis-(diphenylphosphino)propane; sodium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; for 48h; Inert atmosphere;A 18%
B 31%
4-bromo-9H-fluorene
19459-33-7

4-bromo-9H-fluorene

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

4-aminofluorenone
4269-15-2

4-aminofluorenone

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

Conditions
ConditionsYield
With hydrogen bromide Diazotization.Erhitzen mit CuBr und wss. HBr;
(2-amino-3-bromophenyl)(phenyl)methanone

(2-amino-3-bromophenyl)(phenyl)methanone

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

4-Brom-1-amino-fluorenon-(9)
16149-47-6

4-Brom-1-amino-fluorenon-(9)

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

Conditions
ConditionsYield
(i) NaNO2, aq. HCl, (ii) H3PO2; Multistep reaction;
2'-bromo-biphenyl-carboxylic acid-(2)

2'-bromo-biphenyl-carboxylic acid-(2)

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

Conditions
ConditionsYield
With sulfuric acid at 45 - 50℃;
4-bromo-fluoren-9-ol
99514-93-9

4-bromo-fluoren-9-ol

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid; aqueous HI
2: acetic acid; Na2Cr2O7
View Scheme
1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Cu
2: Py / dimethylformamide
3: aq. H2SO4
View Scheme
2,2'-dibromobiphenyl
13029-09-9

2,2'-dibromobiphenyl

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Py / dimethylformamide
2: aq. H2SO4
View Scheme
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C / Inert atmosphere
1.2: Inert atmosphere
2.1: sulfuric acid / water / 2 h / 50 °C
View Scheme
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: 18 h / -78 - 20 °C
2.1: sulfuric acid / 2 h / 0 - 50 °C
View Scheme
1-amino-9H-fluoren-9-one
6344-62-3

1-amino-9H-fluoren-9-one

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Br2, AcOH
2: (i) NaNO2, aq. HCl, (ii) H3PO2
View Scheme
2'-bromo-[1,1'-biphenyl]-2-carboxylic acid
69200-16-4

2'-bromo-[1,1'-biphenyl]-2-carboxylic acid

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

Conditions
ConditionsYield
With sulfuric acid In water at 50℃; for 2h;
With sulfuric acid at 0 - 50℃; for 2h;36 g
1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

o-cyanophenylboronic acid-1,3-propylene glycol ester
172732-52-4

o-cyanophenylboronic acid-1,3-propylene glycol ester

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Pd(PPh3)2Cl2; tripotassium phosphate "n" hydrate / toluene / 12 h / 100 °C / Schlenk technique; Inert atmosphere
2: water; silver trifluoroacetate; dichloro bis(acetonitrile) palladium(II) / trifluoroacetic acid; N,N-dimethyl acetamide / 72 h / 140 °C / Glovebox; Inert atmosphere
View Scheme
2-Cyanophenylboronic acid
138642-62-3

2-Cyanophenylboronic acid

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: toluene / 2 h / 110 °C
2: Pd(PPh3)2Cl2; tripotassium phosphate "n" hydrate / toluene / 12 h / 100 °C / Schlenk technique; Inert atmosphere
3: water; silver trifluoroacetate; dichloro bis(acetonitrile) palladium(II) / trifluoroacetic acid; N,N-dimethyl acetamide / 72 h / 140 °C / Glovebox; Inert atmosphere
View Scheme
methyl 2-iodo-3-bromobenzoate
121772-84-7

methyl 2-iodo-3-bromobenzoate

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / Inert atmosphere
1.2: 0.33 h / Reflux
2.1: sodium hydroxide; ethanol / 6 h
3.1: methanesulfonic acid / 24 h / 30 °C
View Scheme
Multi-step reaction with 3 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / Inert atmosphere
1.2: Reflux
2.1: sodium hydroxide / ethanol / 6 h / Reflux
3.1: methanesulfonic acid / 24 h / 30 °C
View Scheme
phenylboronic acid
98-80-6

phenylboronic acid

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / Inert atmosphere
1.2: 0.33 h / Reflux
2.1: sodium hydroxide; ethanol / 6 h
3.1: methanesulfonic acid / 24 h / 30 °C
View Scheme
Multi-step reaction with 3 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / Inert atmosphere
1.2: Reflux
2.1: sodium hydroxide / ethanol / 6 h / Reflux
3.1: methanesulfonic acid / 24 h / 30 °C
View Scheme
C14H11BrO2

C14H11BrO2

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide; ethanol / 6 h
2: methanesulfonic acid / 24 h / 30 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium hydroxide / ethanol / 6 h / Reflux
2: methanesulfonic acid / 24 h / 30 °C
View Scheme
6-bromo-biphenyl-2-carboxylic acid

6-bromo-biphenyl-2-carboxylic acid

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

Conditions
ConditionsYield
With methanesulfonic acid at 30℃; for 24h;
With methanesulfonic acid at 30℃; for 24h;
4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

2-bromo-9-phenyl-9H-fluoren-9-ol
736928-22-6

2-bromo-9-phenyl-9H-fluoren-9-ol

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 0.333333h;100%
9-(2-bromophenyl)-9H-carbazole
902518-11-0

9-(2-bromophenyl)-9H-carbazole

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

C31H18BrN

C31H18BrN

Conditions
ConditionsYield
Stage #1: 9-(2-bromophenyl)-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran; hexane at -78℃; for 3.67h;
Stage #3: With sulfuric acid; acetic acid for 4h; Reflux;
97%
Stage #1: 9-(2-bromophenyl)-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran; hexane at -78 - 20℃; for 3.66667h;
97%
Stage #1: 9-(2-bromophenyl)-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran; hexane at -78 - 20℃; for 3.67h;
Stage #3: With sulfuric acid; acetic acid for 4h; Reflux;
97%
Stage #1: 9-(2-bromophenyl)-9H-carbazole With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;
Stage #3: With hydrogenchloride; acetic acid for 12h; Reflux;
65%
4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

2,4,7-tribromo-9H-fluoren-9-one

2,4,7-tribromo-9H-fluoren-9-one

Conditions
ConditionsYield
With bromine In dichloromethane at 0 - 20℃; for 6h;92%
With bromine In dichloromethane at 20℃; for 6h;90%
With bromine In dichloromethane at 20℃; for 6h; Cooling with ice;90%
4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

2,3-di-(4-tert-butylphenyl)-1,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene

2,3-di-(4-tert-butylphenyl)-1,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene

4,4'-(4,4''-di-tert-butyl-[1,1':2',1''-terphenyl]-3',6'-diyl)bis(9H-fluoren-9-one)

4,4'-(4,4''-di-tert-butyl-[1,1':2',1''-terphenyl]-3',6'-diyl)bis(9H-fluoren-9-one)

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium carbonate; XPhos In 1,4-dioxane; water at 100℃; for 24h; Suzuki Coupling; Schlenk technique; Sealed tube; Inert atmosphere;91%
4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

phenol
108-95-2

phenol

4-bromospiro[fluorene-9,9′-xanthene]

4-bromospiro[fluorene-9,9′-xanthene]

Conditions
ConditionsYield
With trichlorophosphate at 120℃;87%
With trichlorophosphate
4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

1-(2-bromophenyl)naphthalene
18937-92-3

1-(2-bromophenyl)naphthalene

C29H19BrO

C29H19BrO

Conditions
ConditionsYield
Stage #1: 1-(2-bromophenyl)naphthalene With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere;
Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #3: With water In tetrahydrofuran Inert atmosphere;
85.7%
Stage #1: 1-(2-bromophenyl)naphthalene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran; hexane at -78 - 20℃;
84%
Stage #1: 1-(2-bromophenyl)naphthalene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;
Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran at -78 - 20℃; for 12h; Inert atmosphere;
Stage #3: With hydrogenchloride In tetrahydrofuran; water for 0.5h; Inert atmosphere;
4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

2-bromo-4,4’-dichloro-1,1’-biphenyl
179526-95-5

2-bromo-4,4’-dichloro-1,1’-biphenyl

C25H16BrClO

C25H16BrClO

Conditions
ConditionsYield
Stage #1: 2-bromo-4,4’-dichloro-1,1’-biphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran; hexane at 20℃; for 1h;
85%
4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

phenylboronic acid
98-80-6

phenylboronic acid

4-phenyl-9H-fluoren-9-one
4269-14-1

4-phenyl-9H-fluoren-9-one

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In N,N-dimethyl-formamide at 150℃; Suzuki-Miyaura Coupling; Inert atmosphere;84%
4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

2-nitrophenylboronic acid
5570-19-4

2-nitrophenylboronic acid

C19H11NO3

C19H11NO3

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); bis(tri-t-butylphosphine)palladium(0); potassium carbonate In tetrahydrofuran; water for 2h; Reflux;84%
9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole
785051-54-9

9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

4-(4-(9Hcarbazol-9-yl)phenyl)-9H-fluoren-9-one

4-(4-(9Hcarbazol-9-yl)phenyl)-9H-fluoren-9-one

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; Suzuki-Miyaura Coupling; Inert atmosphere;82%
2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1161009-89-7

2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

4-(9,9'-spirobifluorene-4-yl)-9H-fluoren-9-one
1257321-43-9

4-(9,9'-spirobifluorene-4-yl)-9H-fluoren-9-one

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water for 48h; Suzuki coupling; Reflux; Inert atmosphere;81%
4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

2-(2-bromophenyl)dibenzo[b,e][1,4]dioxine

2-(2-bromophenyl)dibenzo[b,e][1,4]dioxine

4-bromo-9-(2-(dibenzo[b,e][1,4]dioxin-2-yl)phenyl)-9H-fluoren-9-ol

4-bromo-9-(2-(dibenzo[b,e][1,4]dioxin-2-yl)phenyl)-9H-fluoren-9-ol

Conditions
ConditionsYield
Stage #1: 2-(2-bromophenyl)dibenzo[b,e][1,4]dioxine With n-butyllithium In tetrahydrofuran at -78℃; for 1h;
Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran at 20℃; for 3h;
80%
4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

2,5-di-(4-tert-butylphenyl)-1,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene

2,5-di-(4-tert-butylphenyl)-1,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene

4,4'-(4,4''-di-tert-butyl-[1,1':4',1''-terphenyl]-2',5'-diyl)bis(9H-fluoren-9-one)

4,4'-(4,4''-di-tert-butyl-[1,1':4',1''-terphenyl]-2',5'-diyl)bis(9H-fluoren-9-one)

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium carbonate; XPhos In 1,4-dioxane; water at 100℃; for 24h; Suzuki Coupling; Schlenk technique; Sealed tube; Inert atmosphere;79%
4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

C18H11Br

C18H11Br

C31H17Br

C31H17Br

Conditions
ConditionsYield
Stage #1: C18H11Br With n-butyllithium In tetrahydrofuran; hexane at -78 - 70℃; for 0.5h; Inert atmosphere;
Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran; hexane for 1.5h; Inert atmosphere;
Stage #3: With hydrogenchloride; acetic acid for 4h; Reflux;
78%
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
61676-62-8

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1161009-89-7

2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 1h; Inert atmosphere;77%
4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

1-(2-bromophenyl)naphthalene
18937-92-3

1-(2-bromophenyl)naphthalene

C29H17Br

C29H17Br

Conditions
ConditionsYield
Stage #1: 1-(2-bromophenyl)naphthalene With n-butyllithium In tetrahydrofuran at -78℃; for 1h;
Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran at 18 - 28℃; for 12h;
Stage #3: With hydrogenchloride; acetic acid at 120℃; for 5h;
75%
4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

N-(2-bromophenyl)-N-phenylbenzenamine
78600-31-4

N-(2-bromophenyl)-N-phenylbenzenamine

4'-bromo-10-phenyl-10H-spiro[acridine-9,9'-fluorene]

4'-bromo-10-phenyl-10H-spiro[acridine-9,9'-fluorene]

Conditions
ConditionsYield
Stage #1: N-(2-bromophenyl)-N-phenylbenzenamine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Schlenk technique; Glovebox;
Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran; hexane at -78 - 25℃; for 21h; Inert atmosphere; Schlenk technique; Glovebox;
73%
Stage #1: N-(2-bromophenyl)-N-phenylbenzenamine With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Schlenk technique;
Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran; hexane at -78 - 20℃; for 13h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique;
Stage #3: With hydrogenchloride; acetic acid In water for 2h; Reflux;
56%
Stage #1: 4-bromo-9H-fluorene-9-one; N-(2-bromophenyl)-N-phenylbenzenamine With n-butyllithium In tetrahydrofuran
Stage #2: With hydrogenchloride; acetic acid
4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

2-iodobiphenyl
2113-51-1

2-iodobiphenyl

C25H17BrO

C25H17BrO

Conditions
ConditionsYield
Stage #1: 2-iodobiphenyl With n-butyllithium In tetrahydrofuran at -78℃; for 1h;
Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran
73%
4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

C36H26N4

C36H26N4

C49H32N4O

C49H32N4O

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium t-butanolate In toluene for 14h; Inert atmosphere; Reflux;73%
4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

C18H11Br

C18H11Br

C31H17Br

C31H17Br

Conditions
ConditionsYield
Stage #1: C18H11Br With n-butyllithium In tetrahydrofuran; hexane at -78 - -70℃; for 0.5h; Inert atmosphere;
Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran; hexane at -70 - 20℃; for 1.5h; Inert atmosphere;
Stage #3: With hydrogenchloride; acetic acid In water for 4h; Reflux;
73%
9-(2-bromophenyl)-9H-carbazole
902518-11-0

9-(2-bromophenyl)-9H-carbazole

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

C31H20BrNO

C31H20BrNO

Conditions
ConditionsYield
Stage #1: 9-(2-bromophenyl)-9H-carbazole With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran at -78 - 20℃;
72%
With n-butyllithium In tetrahydrofuran at -78℃;
4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

10-(2-bromophenyl)-10H-phenoxazine
131013-62-2

10-(2-bromophenyl)-10H-phenoxazine

4-bromooxacyclospirofluorenetriphenylamine

4-bromooxacyclospirofluorenetriphenylamine

Conditions
ConditionsYield
Stage #1: 10-(2-bromophenyl)-10H-phenoxazine With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran at -78 - 20℃; for 13h; Inert atmosphere;
70%
Stage #1: 10-(2-bromophenyl)-10H-phenoxazine With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;
Stage #3: With hydrogenchloride; acetic acid for 12h; Reflux;
62%
4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

1-(2-bromophenoxy)naphthalene

1-(2-bromophenoxy)naphthalene

4-bromo-9-(2-(naphthalen-1-yloxy)phenyl)-9H-fluoren-9-ol

4-bromo-9-(2-(naphthalen-1-yloxy)phenyl)-9H-fluoren-9-ol

Conditions
ConditionsYield
Stage #1: 1-(2-bromophenoxy)naphthalene With n-butyllithium In tetrahydrofuran at -78℃; for 3.5h; Inert atmosphere;
Stage #2: 4-bromo-9H-fluorene-9-one With n-butyllithium In tetrahydrofuran for 12h; Inert atmosphere;
67%
4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

C18H13Br

C18H13Br

C31H19Br

C31H19Br

Conditions
ConditionsYield
Stage #1: C18H13Br With n-butyllithium In tetrahydrofuran; hexane at -78 - -70℃; for 0.5h; Inert atmosphere;
Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran; hexane at -70 - 20℃; for 1.5h; Inert atmosphere;
Stage #3: With hydrogenchloride; acetic acid In water for 4h; Reflux;
66%
4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

4-(2-bromophenyl)-dibenzothiophene
143546-42-3

4-(2-bromophenyl)-dibenzothiophene

C31H17BrS

C31H17BrS

Conditions
ConditionsYield
Stage #1: 4-(2-bromophenyl)-dibenzothiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran; hexane at 20℃;
Stage #3: With hydrogenchloride In ethanol at 75℃;
65%
4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

2-bromo-3-phenylfuran

2-bromo-3-phenylfuran

4-bromospiro[fluorene-9,8'-indeno[2,1-b]furan]

4-bromospiro[fluorene-9,8'-indeno[2,1-b]furan]

Conditions
ConditionsYield
Stage #1: 2-bromo-3-phenylfuran With magnesium In tetrahydrofuran at 40℃; for 1h; Inert atmosphere;
Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran for 5h; Reflux; Inert atmosphere;
55.1%
4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

4-N,N-diphenylamino-1-bromobenzene
36809-26-4

4-N,N-diphenylamino-1-bromobenzene

C31H22BrO2P

C31H22BrO2P

Conditions
ConditionsYield
Stage #1: 4-N,N-diphenylamino-1-bromobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
50%

4269-17-4Relevant articles and documents

Synthesis of Cyclopenta-HBCs and their Regioselective Chlorination During Oxidative Cyclodehydrogenation

Hall, Thomas B. J.,Hoggard, Bryce R.,Larsen, Christopher B.,Lucas, Nigel T.

, p. 1106 - 1110 (2019)

Hexa-peri-hexabenzocoronenes with a bay-fused five-membered ring are synthesized from fluorenyl precursors. The key oxidative cyclodehydrogenation step is accompanied by regioselective chlorination that is enhanced by methylation at the cyclopenta-ring or increased reaction concentration. The CpHBC products undergo mild electrophilic aromatic bromination, without catalyst, to afford adducts suitable for π-extension by cross-coupling.

Hole transport material and organic electroluminescent device containing same

-

Paragraph 0057; 0060-0061; 0094; 0097-0098; 0197; 0200-0201, (2021/02/24)

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.

Intermediate 5 - bromine yinyin alkone preparation method (by machine translation)

-

Paragraph 0008; 0010-0029, (2019/04/17)

The invention discloses an intermediate 5 - bromine yinyin alkone synthetic method, bromobenzene, dichloromethane, 3 - [...], concentrated hydrochloric acid, NaOH, 1 - tert-butyl 3 - methyl imidazole pressure concentrated water, double-(trifluoromethyl sulfonyl) imide as a main raw material, the process of the invention using the composite catalyst to avoid the corrosion of the equipment, the reaction conditions are easy to control, the yield is high, the product is easy to purification, and the reaction of the raw material 3 - chloropropionyl cheap and bromobenzene. To sum up, the preparation process have very good economic benefits can be the large-scale production. (by machine translation)

Aromatic amine compound containing 9,9'-spirobifluorene and dibenzothiophene and organic electroluminescent device thereof

-

Paragraph 0059; 0063; 0064, (2018/11/03)

The invention provides an aromatic amine compound containing 9,9'-spirobifluorene and dibenzothiophene and an organic electroluminescent device thereof, and relates to the technical field of organic photoelectric materials. The compound has a simple preparation method, easily available raw materials, good hole transport capability and stability, can realize charge balance in a light-emitting layer, has a suitable highest occupied molecular orbital energy level, a high T1 value and a high refractive index, can remarkably improve the light emitting efficiency, the heat resistance and the servicelife of the device when applied to an OLED device, and can also effectively reduce the driving voltage of the device, thereby being an OLED material with excellent performance.

A containing 9, 9' - fluorene and dibenzofuran aromatic amine compound and its organic electroluminescent device (by machine translation)

-

Paragraph 0060; 0064; 0065, (2018/11/04)

The present invention provides a containing 9, 9' - fluorene and dibenzofuran aromatic amine compound and its organic electroluminescent light emitting device, relates to organic photoelectric material technical field. The compound preparation method is simple, easily available raw materials, has suitable the highest occupied molecular orbital energy level, high T1 value and high refractive index, and have very good hole transporting capability, thermal stability and film-forming properties, is applied to the OLED devices, can significantly improve the luminous efficiency of the device, heat resistance and service life, also can effectively reduce the driving voltage of the device. (by machine translation)

COMPOUND, COMPOSITION AND ORGANIC LIGHT-EMITTING DEVICE

-

, (2017/09/15)

A compound of formula (I) or (III) (Formulae (I), (III)) wherein: one Y is a substituent R1 bound directly to the fluorene unit of formula (I) by an sp3-hybridised carbon atom; the other Y is an aryl or heteroaryl group Ar1 that may be unsubstituted or substituted with one or more substituents; Ar2 is an arylene or heteroarylene group; R2 is a substituent; b is 0, 1, 2, 3 or 4; c is 0, 1, 2 or 3; and X is a group of formula (II): (Formula (II)) wherein Z is O or S; R3 independently in each occurrence is a substituent; each x is independently 0, 1, 2 or 3; and * is a bond to the fluorene unit of formula (I).The compounds may be used as host materials for phosphorescent dopants in organic light-emitting devices.

Production method for 4-bromo fluorenone

-

Paragraph 0006; 0016, (2016/10/31)

The invention discloses a production method for 4-bromo fluorenone, belonging to the field of organic chemical synthesis. The production method is realized by comprising the following steps: reacting cyanobenzene as a raw material with o-dibromobenzene under the protection of argon gas and the actions of a palladium catalyst, a copper catalyst and an organic phosphine ligand so as to obtain 2-bromo-2'-carbonitrile biphenyl, and carrying out hydrolyzation and closed-loop synthesizing so as to obtain the 4-bromo fluorenone. The production method for the 4-bromo fluorenone is simple to operate in reaction process, has low production cost and is suitable for industrial production. The 4-bromo fluorenone can be applied in the fields of organic optoelectronic materials, medicines, pesticides, etc.

Atropo-diastereoselective coupling of aryllithiums and arynes — variations around the chiral auxiliary

Augros, David,Yalcouye, Boubacar,Berthelot-Bréhier, Ana?s,Chessé, Matthieu,Choppin, Sabine,Panossian, Armen,Leroux, Frédéric R.

, p. 5208 - 5220 (2016/08/02)

The atropo-selective coupling of in situ generated arynes and aryllithiums bearing various chiral auxiliaries ortho to lithium (tert-butylsulfoxide, para-tolylsulfoxide, tartrate-derived chiral diethers and oxazolines) is described. Chiral oxazolines showed the best results in terms of yields of coupling products. Different reaction parameters like the nature of the aryne precursor, the oxazoline, the alkyllithium base or the solvent revealed to be crucial for obtaining good yields and for diastereoselection.

Access to Atropisomerically En-riched Biaryls by the Coupling of Aryllithiums with Arynes under Control by Homochiral Oxazolines

Yalcouye, Boubacar,Berthelot-Bréhier, Ana?s,Augros, David,Panossian, Armen,Choppin, Sabine,Chessé, Matthieu,Colobert, Fran?oise,Leroux, Frédéric R.

supporting information, p. 725 - 732 (2017/01/18)

We report the preparation of axially stereoenriched biphenyls by the coupling of in situ generated aryllithiums and arynes using chiral oxazoline auxiliaries. The design of the aryne precursors, the choice of oxazoline and the reaction conditions were key to accessing the desired, highly substituted, atropisomerically enriched biarylic products. In one case, the two atropo-diastereomers could be obtained in isomerically pure form by column chromatographic separation and their absolute configurations established by X-ray crystallography. The stereoselectivity of the reaction seems to be governed by subtle parameters.

RhI-Catalyzed Intramolecular Carbonylative C?H/C?I Coupling of 2-Iodobiphenyls Using Furfural as a Carbonyl Source

Furusawa, Takuma,Morimoto, Tsumoru,Nishiyama, Yasuhiro,Tanimoto, Hiroki,Kakiuchi, Kiyomi

supporting information, p. 2312 - 2315 (2016/08/30)

Synthesis of fluoren-9-ones by a Rh-catalyzed intramolecular C?H/C?I carbonylative coupling of 2-iodobiphenyls using furfural as a carbonyl source is presented. The findings indicate that the rate-determining step is not a C?H bond cleavage but, rather, the oxidative addition of the C?I bond to a RhI center.

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