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28320-32-3

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28320-32-3 Usage

Chemical Properties

White solid

Uses

This material is a precursor to a number of organic semiconducting polymers for OPV as well as a variety of hole transport for OLED devices.

Check Digit Verification of cas no

The CAS Registry Mumber 28320-32-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,8,3,2 and 0 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 28320-32:
(7*2)+(6*8)+(5*3)+(4*2)+(3*0)+(2*3)+(1*2)=93
93 % 10 = 3
So 28320-32-3 is a valid CAS Registry Number.
InChI:InChI=1/C15H12Br2/c1-15(2)13-7-9(16)3-5-11(13)12-6-4-10(17)8-14(12)15/h3-8H,1-2H3

28320-32-3 Well-known Company Product Price

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  • TCI America

  • (D3859)  2,7-Dibromo-9,9-dimethylfluorene  >98.0%(HPLC)

  • 28320-32-3

  • 5g

  • 990.00CNY

  • Detail
  • TCI America

  • (D3859)  2,7-Dibromo-9,9-dimethylfluorene  >98.0%(HPLC)

  • 28320-32-3

  • 25g

  • 3,850.00CNY

  • Detail
  • Aldrich

  • (757187)  2,7-Dibromo-9,9-dimethyl-9H-fluorene  99%

  • 28320-32-3

  • 757187-5G

  • 1,891.89CNY

  • Detail

28320-32-3SDS

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 2,7-Dibromo-9,9-dimethylfluorene

1.2 Other means of identification

Product number -
Other names 2,7-dibromo-9,9-dimethyl-9H-fluorene

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

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More Details:28320-32-3 SDS

28320-32-3Synthetic route

2,7-dibromo-9H-fluorene
16433-88-8

2,7-dibromo-9H-fluorene

methyl iodide
74-88-4

methyl iodide

2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium hydroxide In dimethyl sulfoxide for 5h; Sonication;99%
With tetrabutylammomium bromide; sodium hydroxide In dimethyl sulfoxide at 20℃; for 5h; Sonication;99%
With tetrabutylammomium bromide; sodium hydroxide In dimethyl sulfoxide for 5h; Sonication;99%
2,7-dibromo-9H-fluorene
16433-88-8

2,7-dibromo-9H-fluorene

2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium hydroxide In dimethyl sulfoxide at 20℃; for 5h;99%
9,9-dimethyl-9H-fluorene
4569-45-3

9,9-dimethyl-9H-fluorene

2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

Conditions
ConditionsYield
With bromine In chloroform for 4h; Cooling with ice;76%
With bromine
methyl iodide
74-88-4

methyl iodide

2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

Conditions
ConditionsYield
Stage #1: 2,7-dibromo-9H-fluorene With potassium tert-butylate In dimethyl sulfoxide at 5℃;
Stage #2: methyl iodide In dimethyl sulfoxide at 5℃;
2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

3,5-bis-trifluromethylphenylboronic acid
73852-19-4

3,5-bis-trifluromethylphenylboronic acid

C31H18F12

C31H18F12

Conditions
ConditionsYield
With potassium carbonate In ethanol; water at 80℃; for 1.5h; Suzuki Coupling;98%
2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

2,7-bis(trimethylstannyl)-9,9-dimethylfluorene
1228237-11-3

2,7-bis(trimethylstannyl)-9,9-dimethylfluorene

Conditions
ConditionsYield
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 1.25h;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at -78 - 20℃; for 6.08333h;
97%
2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

dimesitylfluoroborane
436-59-9

dimesitylfluoroborane

(7-bromo-9,9-dimethyl-9H-fluoren-2-yl)dimesitylborane
1254106-26-7

(7-bromo-9,9-dimethyl-9H-fluoren-2-yl)dimesitylborane

Conditions
ConditionsYield
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;
Stage #2: dimesitylfluoroborane In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
94%
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h;
Stage #2: dimesitylfluoroborane In tetrahydrofuran; hexane at 20℃; for 6h;
80%
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -78℃;
Stage #2: dimesitylfluoroborane In tetrahydrofuran; hexane for 12h;
63%
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran
Stage #2: dimesitylfluoroborane
4-trifluoromethylphenylamine
455-14-1

4-trifluoromethylphenylamine

2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

C22H17BrF3N
676625-76-6

C22H17BrF3N

Conditions
ConditionsYield
With sodium t-butanolate; C30H48FeP2; palladium dichloride In 1,4-dioxane for 3h; Heating / reflux;92%
With sodium t-butanolate; C30H48FeP2; palladium dichloride In 1,4-dioxane for 3h; Heating / reflux;92 %Chromat.
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

2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

4,4,5,5-tetramethyl-2-[7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9,9-dimethyl-9H-fluoren-2-yl]-[1,3,2]dioxaborolane
325129-69-9

4,4,5,5-tetramethyl-2-[7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9,9-dimethyl-9H-fluoren-2-yl]-[1,3,2]dioxaborolane

Conditions
ConditionsYield
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane at 20℃; for 2h;
90%
With n-butyllithium In diethyl ether at -78 - 20℃; for 14h; Inert atmosphere;60.5%
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran at -78 - 0℃;
Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 20℃;
33%
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;
Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran for 25h;
2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

7-bromo-9,9-dimethyl-9H-fluorene-2-carbaldehyde
944940-90-3

7-bromo-9,9-dimethyl-9H-fluorene-2-carbaldehyde

Conditions
ConditionsYield
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran at -78℃; for 1h;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 20℃; for 2h;
90%
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran at -78℃; for 1h;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78 - 20℃;
90%
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Schlenk technique;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78 - 25℃; for 10h; Inert atmosphere; Schlenk technique;
90%
2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

7-bromo-9,9-dimethyl-9H-fluorene-2-carbaldehyde
944940-90-3

7-bromo-9,9-dimethyl-9H-fluorene-2-carbaldehyde

Conditions
ConditionsYield
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Schlenk technique;
Stage #2: With N,N-dimethyl-formamide In tetrahydrofuran at -78 - 25℃; for 10h; Inert atmosphere; Schlenk technique;
90%
2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

C15H6(2)H6Br2

C15H6(2)H6Br2

Conditions
ConditionsYield
With water-d2; potassium carbonate; silver carbonate; cyclohexyldiphenylphosphine In toluene at 120℃; for 12h;90%
2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

1-pyrenylboronic acid
164461-18-1

1-pyrenylboronic acid

1,1'-(9,9-dimethyl-9H-fluorene-2,7-diyl)bis-pyrene

1,1'-(9,9-dimethyl-9H-fluorene-2,7-diyl)bis-pyrene

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 20 - 77℃; for 5.5h; Suzuki Coupling;89%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 4h; Suzuki Coupling; Reflux;73%
2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

N-methylaniline
100-61-8

N-methylaniline

N2,N7,9,9-tetramethyl-N2,N7-diphenyl-9H-fluorene-2,7-diamine

N2,N7,9,9-tetramethyl-N2,N7-diphenyl-9H-fluorene-2,7-diamine

Conditions
ConditionsYield
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With palladium diacetate; johnphos; sodium t-butanolate In toluene at 20℃; for 0.75h; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique;
Stage #2: N-methylaniline In toluene at 180℃; for 1h; Reagent/catalyst; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique; Microwave irradiation;
89%
((10-(naphthalen-1-yl)anthracen-9-yl)boronic acid)
400607-46-7

((10-(naphthalen-1-yl)anthracen-9-yl)boronic acid)

2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

10-(9,9-dimethyl-2-(10-(naphthalen-1-yl)anthracen-9-yl)-9H-fluoren-7-yl)-9-(naphthalen-1-yl)anthracene

10-(9,9-dimethyl-2-(10-(naphthalen-1-yl)anthracen-9-yl)-9H-fluoren-7-yl)-9-(naphthalen-1-yl)anthracene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 4h; Suzuki Coupling; Reflux;86%
2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

N-methylaniline
100-61-8

N-methylaniline

7-bromo-N,9,9-trimethyl-N-phenyl-9H-fluoren-2-amine

7-bromo-N,9,9-trimethyl-N-phenyl-9H-fluoren-2-amine

Conditions
ConditionsYield
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With palladium diacetate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); sodium t-butanolate In toluene at 20℃; for 0.5h; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique;
Stage #2: N-methylaniline In toluene at 180℃; for 0.75h; Reagent/catalyst; Solvent; Buchwald-Hartwig Coupling; Microwave irradiation; Schlenk technique; Inert atmosphere;
86%
2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

aniline
62-53-3

aniline

C27H24N2

C27H24N2

Conditions
ConditionsYield
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene; aniline In benzene at 50℃; for 0.333333h; Inert atmosphere;
Stage #2: With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In benzene Reflux; Inert atmosphere;
85.63%
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene for 12h; Inert atmosphere;
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene for 12h; Inert atmosphere;
2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrene
349666-24-6

1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrene

1-(7-bromo-9,9-dimethyl-9H-fluoren-2-yl)pyrene
872705-65-2

1-(7-bromo-9,9-dimethyl-9H-fluoren-2-yl)pyrene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 12h; Inert atmosphere; Reflux;85%
2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

C24H13NO2

C24H13NO2

C63H36N2O4

C63H36N2O4

Conditions
ConditionsYield
With tri-tert-butyl phosphine; potassium tert-butylate; palladium diacetate In toluene at 82℃; for 11h;85%
2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

C19H14N2O

C19H14N2O

C53H38N4O2

C53H38N4O2

Conditions
ConditionsYield
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene for 2h; Inert atmosphere; Reflux;85%
2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

9,9-dimethyl-9H-fluoren-2-yl-2-boronic acid
333432-28-3

9,9-dimethyl-9H-fluoren-2-yl-2-boronic acid

9,9-dimethylfluorene trimer

9,9-dimethylfluorene trimer

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water for 14h; Reflux; Inert atmosphere; Schlenk technique;84%
2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

4,4,5,5-tetramethyl-2-[7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9,9-dimethyl-9H-fluoren-2-yl]-[1,3,2]dioxaborolane
325129-69-9

4,4,5,5-tetramethyl-2-[7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9,9-dimethyl-9H-fluoren-2-yl]-[1,3,2]dioxaborolane

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane for 4h; Inert atmosphere; Heating;83%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate at 90℃; for 48h; Inert atmosphere;78%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate at 90℃; for 48h;78%
2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

diphenylamine
122-39-4

diphenylamine

2-bromo-7-N,N’-diphenylamino-9,9’-dimethyl-9H-fluorene
302579-16-4

2-bromo-7-N,N’-diphenylamino-9,9’-dimethyl-9H-fluorene

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 80℃; for 2h; Schlenk technique;83%
With 18-crown-6 ether; copper; potassium carbonate; potassium iodide In 1,2-dichloro-benzene at 200℃; for 24h; Inert atmosphere;79%
With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene at 20 - 200℃; for 24h; Inert atmosphere;79%
pyrrolidine
123-75-1

pyrrolidine

2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

1-(7-bromo-9,9-dimethyl-9H-fluoren-2-yl)pyrrolidine

1-(7-bromo-9,9-dimethyl-9H-fluoren-2-yl)pyrrolidine

Conditions
ConditionsYield
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With palladium diacetate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); sodium t-butanolate In toluene at 20℃; for 0.5h; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique;
Stage #2: pyrrolidine In toluene at 180℃; for 0.75h; Buchwald-Hartwig Coupling; Microwave irradiation; Schlenk technique; Inert atmosphere;
83%
2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

phenylboronic acid
98-80-6

phenylboronic acid

9,9-dimethyl-2,7-diphenyl-9H-fluorene
1009629-20-2

9,9-dimethyl-2,7-diphenyl-9H-fluorene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate In water; toluene at 90℃; Inert atmosphere; Schlenk technique;82.6%
With potassium carbonate In ethanol; water; toluene at 120℃; for 3h; Inert atmosphere;
With potassium carbonate; tetrabutylammomium bromide; palladium diacetate In water at 70℃; for 24h;
Suzuki Coupling;
styrene
292638-84-7

styrene

2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

9,9-dimethyl-2,7-di((E)-styryl)-9H-fluorene

9,9-dimethyl-2,7-di((E)-styryl)-9H-fluorene

Conditions
ConditionsYield
With bis(tri-t-butylphosphine)palladium(0); N-Methyldicyclohexylamine; tetrabutylammomium bromide In toluene at 80℃; Inert atmosphere; Schlenk technique;82.5%
2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

9,9-dimethyl-9H-fluorene-2,7-dicarbaldehyde
1313886-42-8

9,9-dimethyl-9H-fluorene-2,7-dicarbaldehyde

Conditions
ConditionsYield
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Schlenk technique;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; N,N-dimethyl-formamide at -78 - 25℃; for 10h; Inert atmosphere; Schlenk technique;
82%
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With magnesium In tetrahydrofuran for 16h; Grignard reaction; Reflux;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 20℃; for 5h; Cooling with ice;
66%
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran at -78℃; for 1h;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 20℃; for 3h;
62%
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran at -78℃; for 1h;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran for 12h;
60%
2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

aniline
62-53-3

aniline

7-bromo-9,9-dimethyl-N-phenyl-9H-fluoren-2-amine

7-bromo-9,9-dimethyl-N-phenyl-9H-fluoren-2-amine

Conditions
ConditionsYield
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With palladium diacetate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); sodium t-butanolate In toluene at 20℃; for 0.5h; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique;
Stage #2: aniline In toluene at 180℃; for 0.75h; Buchwald-Hartwig Coupling; Microwave irradiation; Schlenk technique; Inert atmosphere;
82%
2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

9,9-dimethyl-9H-fluorene-2,7-dicarbaldehyde
1313886-42-8

9,9-dimethyl-9H-fluorene-2,7-dicarbaldehyde

Conditions
ConditionsYield
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Schlenk technique;
Stage #2: With N,N-dimethyl-formamide In tetrahydrofuran at -78 - 25℃; for 10h; Inert atmosphere; Schlenk technique;
82%
indium tri(4-methylbenzenethiolate)

indium tri(4-methylbenzenethiolate)

2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

2,7-di(p-tolylthio)-9,9-dimethyl-9H-fluorene
1263672-65-6

2,7-di(p-tolylthio)-9,9-dimethyl-9H-fluorene

Conditions
ConditionsYield
With palladium diacetate; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere;81%
1H-imidazole
288-32-4

1H-imidazole

2,7-dibromo-9,9-dimethyl-9H-fluorene
28320-32-3

2,7-dibromo-9,9-dimethyl-9H-fluorene

2,7-bis(1H-imidazol-1-yl)-9,9-dimethyl-9H-fluorene
1588929-66-1

2,7-bis(1H-imidazol-1-yl)-9,9-dimethyl-9H-fluorene

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 120℃; for 8h; Inert atmosphere;81%
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 119.84℃; for 36h; Inert atmosphere;76.1%
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 120℃; for 8h;76%

28320-32-3Relevant articles and documents

Tricolor Luminescence Switching by Thermal and Mechanical Stimuli in the Crystal Polymorphs of Pyridyl-substituted Fluorene

Guan, Jianping,Xu, Fan,Tian, Chang,Pu, Liang,Yuan, Mao-Sen,Wang, Jinyi

, p. 216 - 222 (2019)

Stimuli-responsive organic luminescence-switching materials have attracted much attention for a decade. Most of the reported examples display a reversible two-color luminescence switching, and multicolor-switching materials remain extremely rare. Herein, we report a simple organic molecule, 4,4′-(9,9-dimethyl-9H-fluorene-2,7-diyl)dipyridine (MFDP), which exhibits three different crystal polymorphs (V-MFDP, B-MFDP and G-MFDP) with different luminescent colors. Furthermore, the three crystal polymorphs show a reversible tricolor fluorescent switching from violet to blue and to green upon physical stimuli. The single-crystal structures of the three polymorphs were obtained, and the results indicate that the stimuli-responsive properties of the three polymorphs come from the different stacking modes induced by intermolecular interactions. The competition between weak π–π stacking and weak hydrogen bonding is the main reason for the the phase transformations among the three crystal polymorphs.

Bifunctional fluorescent quenching detection of 2,4,6-trinitrophenol (TNP) and acetate ions via 4,4′-(9,9-dimethyl-9H-fluorene-2,7-diyl)dibenzoic acid

Ni, Jue Chen,Yan, Jie,Zhang, Li Jing,Shang, Di,Du, Ning,Li, Shuang,Zhao, Jin Xin,Wang, Yang,Xing, Yong Heng

, p. 4978 - 4982 (2016)

The 4,4′-(9,9-dimethylfluorene-2,7-diyl)dibenzoic acid (5) was synthesized using commercial fluorene as the starting material followed by processes of bromination, methylation, Suzuki coupling and hydrolysis. We reported it as an exclusive fluorescence sensor for 2,4,6-trinitrophenol (TNP) and acetate ions for the first time. The experimental results suggested a high efficiency for TNP detection with KSVvalues of 21,215?M?1, which has achieved to micromolar level (10?μM) of this material. Moreover, the detection limit (1.39?×?10?6?M) was measured according to the fluorescence intensity changes of Ac?in CH3CN.

Self-repairing platinum metal gel material as well as preparation method and application thereof

-

Paragraph 0126-0127, (2021/11/21)

The invention discloses a self-repairing platinum metal gel and a preparation method and application thereof, and belongs to the field of self-repair metal gel materials. A self-healing platinum metal gel Pt-4 CHO, having the structure of Formula I, by performing a series of substitution reactions to the feedstock 2, 7 - dibromo - 9H - fluorene. With sonogashira-and CHO aldehyde group conversion into imine-based synthetic model molecule Pt 4 Pt 4 Pt-4 imine through Schiff base reaction, the prepared platinum metal gel has good self-repairing property, optical transparency, mechanical property and light-limiting property, and laser protection performance is further improved due to nonlinear scattering of laser in the gel.

Clickable azide-functionalized bromoarylaldehydes – synthesis and photophysical characterization

Friedrich, Marius,G?bel, Dominik,Lork, Enno,Nachtsheim, Boris J.

supporting information, p. 1683 - 1692 (2021/06/25)

Herein, we present a facile synthesis of three azide-functionalized fluorophores and their covalent attachment as triazoles in Huisgen-type cycloadditions with model alkynes. Besides two ortho- and para-bromo-substituted benzaldehydes, the azide functionalization of a fluorene-based structure will be presented. The copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) of the so-synthesized azide-functionalized bromocarbaldehydes with terminal alkynes, exhibiting different degrees of steric demand, was performed in high efficiency. Finally, we investigated the photophysical properties of the azide-functionalized arenes and their covalently linked triazole derivatives to gain deeper insight towards the effect of these covalent linkers on the emission behavior.

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