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Product Details
Uses |
2-Bromo-9,9-dimethylfluorene is a fluorene derivative which shows π-electron conjugation. It has a high fluorescent and high electron delocalization. It can be used as a non-linear optical (NLO) material. 2-bromo-9, 9-diphenylfluorene can be synthesized by using 2-bromofluorene and iodomethane as the major reactants. It can be majorly used in organic electronic based applications. |
Description |
2-bromo-9, 9-diphenylfluorene appears as an off-white solid. It belongs to the fluorene group compound. It is a kind of OLED (organic light-emitting diodes) intermediate. It can be used for the production of 9, 9-diphenylfluorene-capped oligothiophenes which can be used as active materials such as filed-effect transistors and light-emitting diodes. |
Chemical Properties |
off-white powder |
Synthesis |
10 g (30 mmol) of 2-bromo-9-phenyl-9H-fluoren-9-ol was dissolved in 60 ml of benzene, and 2.4 ml (45 mmol) of concentrated sulfuric acid diluted with a small amount of benzene was added to the solution. The mixture was stirred for 5 hours at 80° C, and after evaporating the benzene, 1 N sodium hydroxide solution was added to the remaining solution to a pH of around 7. The mixture was extracted 3 times with ethyl acetate (40 ml). The collected organic layer was dried with magnesium sulfate, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography. 6 g of Intermediate N (yield: 50%). |
References |
(2015). Synthesis method of 2-bromo-9, 9-diphenylfluorene, Google Patents. Wong, Ken-Tsung, et al. "Synthesis and properties of novel thiophene-based conjugated homologues: 9, 9-diphenylfluorene-capped oligothiophenes."Organic letters 4.25 (2002): 4439-4442. |
InChI:InChI=1/C25H17Br/c26-20-15-16-22-21-13-7-8-14-23(21)25(24(22)17-20,18-9-3-1-4-10-18)19-11-5-2-6-12-19/h1-17H
The invention discloses a preparation me...
The invention discloses a synthetic meth...
The invention provides a synthesis metho...
The invention relates to a one-pot metho...
2-bromo-9-phenyl-9-hydroxyfluorene
benzene
2-bromo-9,9-diphenyl-9H-fluorene
Conditions | Yield |
---|---|
With aluminum (III) chloride; trifluoroacetic acid; at 45 - 75 ℃; for 5.5h; Temperature; Inert atmosphere;
|
98.6% |
2-bromo-9-phenyl-9-hydroxyfluorene; benzene; With hydrogen bromide; at 64 ℃; for 2h;
at 45 ℃; for 5h; Reagent/catalyst; Temperature; Catalytic behavior;
|
95.1% |
With trifluorormethanesulfonic acid; for 4h; Reflux; Inert atmosphere;
|
92% |
With sulfuric acid; for 3h;
|
|
With trifluorormethanesulfonic acid; Reflux;
|
2 g |
With trifluorormethanesulfonic acid; Heating;
|
2-bromofluoren-9-one
2-bromo-9,9-diphenyl-9H-fluorene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps
1: diethyl ether / 3 h / Heating
2: conc. H2SO4 / 3 h
With sulfuric acid; In diethyl ether; 1: Grignard reaction / 2: Friedel-Crafts reaction;
|
|
Multi-step reaction with 2 steps
1.1: magnesium / diethyl ether / 4 h / Reflux
1.2: Reflux
2.1: trifluorormethanesulfonic acid / Heating
With trifluorormethanesulfonic acid; magnesium; In diethyl ether;
|
|
Multi-step reaction with 2 steps
1: tetrahydrofuran / 5.5 h / -78 - 40 °C
2: trifluorormethanesulfonic acid / 4 h / Reflux; Inert atmosphere
With trifluorormethanesulfonic acid; In tetrahydrofuran;
|
2-bromo-9-phenyl-9-hydroxyfluorene
benzene
2-bromofluoren-9-one
bromobenzene
2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-diphenyl-9H-fluorene
C62H44Si
C54H46OSi2
C31H22
CAS:28320-31-2
Molecular Formula:C<sub>15</sub>H<sub>13</sub>Br
Molecular Weight:273.17
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