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2,7-Dibromofluorene

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2,7-Dibromofluorene Basic information
Product Name:2,7-Dibromofluorene
Synonyms:2,7-DIBROMOFLUORENE;Aluminum oxide, fused, #325 mesh, 99+%;Dibromofluorene;TIMTEC-BB SBB007691;2,7-Dibromofluorene, 98+%;2,7-Dibromo-9H-fluorene;Fluorene, 2,7-dibromo-;2,7-Dibromofluorene,99%
CAS:16433-88-8
MF:C13H8Br2
MW:324.01
EINECS:629-430-2
Product Categories:Thiadiazoles ,Benzothiazoles;OLED materials,pharm chemical,electronic;Fluorene Series;Halogenated Hydrocarbons;blocks;Bromides;Fluorenes, Flurenones;Fluorene Derivatives;Fluorenes;Fluorenes & Fluorenones;Aryl;C13 to C37+;16433-88-8
Mol File:16433-88-8.mol
2,7-Dibromofluorene Structure
2,7-Dibromofluorene Chemical Properties
Melting point 164-166 °C (lit.)
Boiling point 329.77°C (rough estimate)
density 1.7203 (estimate)
refractive index 1.6000 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility Chloroform (Slightly)
form Crystalline Powder
color White to off-white
BRN 2049205
InChIInChI=1S/C13H8Br2/c14-10-1-3-12-8(6-10)5-9-7-11(15)2-4-13(9)12/h1-4,6-7H,5H2
InChIKeyAVXFJPFSWLMKSG-UHFFFAOYSA-N
SMILESC1C2=C(C=CC(Br)=C2)C2=C1C=C(Br)C=C2
CAS DataBase Reference16433-88-8(CAS DataBase Reference)
NIST Chemistry Reference9H-fluorene, 2,7-dibromo-(16433-88-8)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-37/39
WGK Germany 3
TSCA T
HazardClass IRRITANT
HS Code 29420000
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
2,7-Dibromofluorene Usage And Synthesis
Description2,7-Dibromofluorene is a halogenated polycyclic aromatic compound and its vapour pressure has been measured using the Knudsen effusion method.
Chemical Propertieswhite to off-white crystalline powder
Uses2,7-Dibromofluorene was used as a template for the N-carbazole capped oligofluorenes which show potential as hole-transporting materials for organic light emitting devices (OLEDs). It may be used in the synthesis of conjugated polymer, poly[9,9′-bis(6′′-N,N,N-trimethylammonium)hexyl)fluorene-co-alt-4,7-(2,1,3-benzothiadiazole) dibromide] (PFBT), used in label-free DNA microarrays. It was used in the preparartion of blue photoluminescent unsymmetrically substituted polyfluorene. It was also used in the preparation of 2,7-dibromofluorene monomers containing benzyl ether dendrons (generations 1, 2 and 3) in the 9,9′-position of the fluorene ring, such as:
9,9-bis[(3,5-bis(benzyloxy)benzyloxy)methyl]-2,7-dibromofluorene
9,9-bis[(3,5-bis(3,5-bis(benzyloxy)benzyloxy)benzyloxy)-methyl] 2,7-dibromo-fluorene
9,9-bis[(3,5-bis(3,5-bis(3,5-bis(benzyloxy)benzyloxy)benzyloxy) benzyloxy)-methyl]-2,7-dibromofluorene
Uses2,7-Dibromofluorene is used as a template for the N-carbazole capped oligofluorenes which show potential as hole-transporting materials for organic light emitting devices (OLEDs). It is also used in the synthesis of conjugated polymer, poly[9,9?-bis(6??-N,N,N-trimethylammonium)hexyl)fluorene-co-alt-4,7-(2,1,3-benzothiadiazole) dibromide] (PFBT), used in label-free DNA microarrays, in the preparation of blue photoluminescent unsymmetrically substituted polyfluorene and in the preparation of 2,7-dibromofluorene monomers containing benzyl ether dendrons (generations 1, 2 and 3) in the 9,9?-position of the fluorene ring, such as: 9,9-bis[(3,5-bis(benzyloxy)benzyloxy)methyl]-2,7-dibromofluorene, 9,9-bis[(3,5-bis(3,5-bis(benzyloxy)benzyloxy)benzyloxy)-methyl] 2,7-dibromo-fluorene, 9,9-bis[(3,5-bis(3,5-bis(3,5-bis(benzyloxy)benzyloxy)benzyloxy) benzyloxy)-methyl]-2,7-dibromofluorene.
Uses2,7-Dibromofluorene was used as a template for the N-carbazole capped oligofluorenes which show potential as hole-transporting materials for organic light emitting devices (OLEDs). It may be used in the synthesis of conjugated polymer, poly[9,9′-bis(6′′-N,N,N-trimethylammonium)hexyl)fluorene-co-alt-4,7-(2,1,3-benzothiadiazole) dibromide] (PFBT), used in label-free DNA microarrays. It was used in the preparartion of blue photoluminescent unsymmetrically substituted polyfluorene. It was also used in the preparation of 2,7-dibromofluorene monomers containing benzyl ether dendrons (generations 1, 2 and 3) in the 9,9′-position of the fluorene ring, such as:
  • 9,9-bis[(3,5-bis(benzyloxy)benzyloxy)methyl]-2,7-dibromofluorene
  • 9,9-bis[(3,5-bis(3,5-bis(benzyloxy)benzyloxy)benzyloxy)-methyl] 2,7-dibromo-fluorene
  • 9,9-bis[(3,5-bis(3,5-bis(3,5-bis(benzyloxy)benzyloxy)benzyloxy) benzyloxy)-methyl]-2,7-dibromofluorene
Synthesis
Fluorene

86-73-7

2,7-Dibromofluorene

16433-88-8

General procedure for the synthesis of 2,7-dibromofluorene from fluorene: Fluorene (1.5 g, 9.0 mmol) was dissolved in carbon tetrachloride (80 mL), followed by the addition of 30 g of copper(II) bromide loaded on aluminum oxide. The reaction mixture was stirred under reflux conditions for 5 hours. Upon completion of the reaction, the solution was cooled to room temperature, filtered to remove solid impurities, and the filter cake was washed with carbon tetrachloride (50 mL). The combined organic phases were dried with anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure to give 2.87 g (98% yield) of 2,7-dibromofluorene as a yellow solid. Recrystallization by ethyl acetate/hexane (5:95, v/v) mixed solvent gave pure 2,7-dibromofluorene as light yellow crystals.

References[1] Tetrahedron, 2003, vol. 59, # 17, p. 3131 - 3156
[2] Dyes and Pigments, 2015, vol. 113, p. 682 - 691
[3] Organic and Biomolecular Chemistry, 2018, vol. 16, # 22, p. 4071 - 4075
[4] Chemistry Letters, 2013, vol. 42, # 11, p. 1355 - 1357
[5] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 2, p. 439 - 443
Tag:2,7-Dibromofluorene(16433-88-8) Related Product Information
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