CN103102245A - Preparation method for 1-dibromopyrene - Google Patents
Preparation method for 1-dibromopyrene Download PDFInfo
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- CN103102245A CN103102245A CN2011103528010A CN201110352801A CN103102245A CN 103102245 A CN103102245 A CN 103102245A CN 2011103528010 A CN2011103528010 A CN 2011103528010A CN 201110352801 A CN201110352801 A CN 201110352801A CN 103102245 A CN103102245 A CN 103102245A
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- bromine
- pyrene
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- dibromopyrene
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- HYGLETVERPVXOS-UHFFFAOYSA-N Brc1c(ccc2c3c(cc4)ccc2)c3c4cc1 Chemical compound Brc1c(ccc2c3c(cc4)ccc2)c3c4cc1 HYGLETVERPVXOS-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention discloses a preparation method for 1-dibromopyrene. The preparation method is characterized by comprising the following steps: dissolving pyrene in an organic solvent; adding dibromohydantoin for a reaction; carrying out filtering; and subjecting an obtained solid to recrystallization so as to obtain 1-dibromopyrene. The preparation method provided by the invention has the advantages of easiness, mild reaction conditions, high yield and convenience in industrial production. In a bromination reaction in the method, dibromohydantoin is employed, and bromination of liquid bromine is avoided, wherein liquid bromine has strong toxicity and corrosivity, and at a normal temperature, liquid bromine can volatilize strongly irritant smog to irritate mucosas of eyes and respiratory tracts, which incurs tearing and coughing of people, and can burn the skin and cause a sharp pain, which is hard to heal. Bromine has active properties, is a strong oxidizing agent, violently reacts and is difficult to control. When hydrobromic acid and hydrogen peroxide are used as brominating agents, considerable strong acid waste water is produced after a reaction is finished, which causes severe pollution.
Description
Technical field
The present invention relates to a kind of preparation method of 1-bromine pyrene.
Background technology
Pyrene is a kind of important chemical intermediate, it can be used for further modifying, and then synthetic organic photoelectrical material, making has the device of organic blue light-emitting in high emission efficiency and long continuous drive life-span, and the aspects such as organic photoelectrical material has been widely used in organic/polymer electroluminescence diode (OLED/PLED), photodetector, organic solar batteries (OSC), device for non-linear optical, organic field effect tube (OFET).Wherein introduce various substituted radicals on the condensed ring of pyrene, as halo, hydroxyl etc., in order to further modify, connect, make organic photoelectrical material.
The synthetic following methods that mainly contains of 1-bromine pyrene: one, adopt the method for the direct bromination of bromine, pyrene in organic solvent, is directly done the bromizating agent bromination with bromine, obtain the bromo pyrene, then obtain 1-bromine pyrene through recrystallization.Two, make bromizating agent with Hydrogen bromide and hydrogen peroxide, directly the bromination pyrene obtains 1-bromine pyrene.
Summary of the invention
It is simple that technical problem to be solved by this invention is to provide a kind of preparation method, and reaction conditions is gentle, the preparation method of the 1-bromine pyrene that productive rate is high.
The structural formula of 1-bromine pyrene is:
The synthetic route of 1-bromine pyrene is:
The preparation process of 1-bromine pyrene comprises the following steps:
Pyrene is dissolved in organic solvent, adds C5H6Br2N2O2 to react, the weight ratio of pyrene and C5H6Br2N2O2 is 1: 0.5-1, filter, and gained solid recrystallization obtains 1-bromine pyrene.
Described organic solvent is preferably methyl alcohol, ethanol, Virahol, tetrahydrofuran (THF), dioxane, DMF or methyl-sulphoxide.
Described reaction is preferably at room temperature carried out, and the reaction times is 10-15h.
Preparation method of the present invention is simple, and reaction conditions is gentle, and productive rate is high, is convenient to suitability for industrialized production.Bromination reaction wherein, adopt C5H6Br2N2O2, avoided employing bromine bromination, and bromine there are extremely strong strong toxic and corrodibility, when normal temperature, can volatilize the smog of intense stimulus, stimulate the mucous membrane of eyes and respiratory tract, draw tears from sb and cough, the energy skin ambustion, produce violent shouting pain, be difficult for curing.The character of bromine is very active, is strong oxidizer, and reaction is violent, and is wayward.Make bromizating agent with Hydrogen bromide and hydrogen peroxide, reaction can produce a large amount of strong acid waste water after finishing, and is seriously polluted.
Embodiment
Synthesizing of embodiment 1:1-bromine pyrene:
Under lucifuge, add pyrene 40g in the 2L four-hole bottle, Virahol 400g, stir half an hour, add C5H6Br2N2O2 30g under room temperature, approximately 2h drips off, after insulation reaction 12h, sampling HPLC detects, and filters gained solid toluene recrystallization, dry, obtain approximately 40g white solid, be 1-bromine pyrene, productive rate 71.9%.
Synthesizing of embodiment 2:1-bromine pyrene:
Under lucifuge, add pyrene 40g in the 2L four-hole bottle, Virahol 400g, stir half an hour, add C5H6Br2N2O2 20g under room temperature, approximately 2h drips off, after insulation reaction 10h, sampling HPLC detects, and filters gained solid toluene recrystallization, dry, obtain approximately 40g white solid, be 1-bromine pyrene, productive rate 71.9%.
Synthesizing of embodiment 3:1-bromine pyrene:
Under lucifuge, add pyrene 40g in the 2L four-hole bottle, Virahol 400g, stir half an hour, add C5H6Br2N2O2 40g under room temperature, approximately 2h drips off, after insulation reaction 15h, sampling HPLC detects, and filters gained solid toluene recrystallization, dry, obtain approximately 40g white solid, be 1-bromine pyrene, productive rate 71.9%.
Claims (3)
1. the preparation method of a 1-bromine pyrene, is characterized in that, comprising: pyrene is dissolved in organic solvent, adds C5H6Br2N2O2 to react, the weight ratio of pyrene and C5H6Br2N2O2 is 1: 0.5-1, filter, and gained solid recrystallization obtains 1-bromine pyrene.
2. the preparation method of 1-bromine pyrene according to claim 1, is characterized in that, described organic solvent is methyl alcohol, ethanol, Virahol, tetrahydrofuran (THF), dioxane, DMF or methyl-sulphoxide.
3. the preparation method of 1-bromine pyrene according to claim 1, is characterized in that, described reaction is at room temperature carried out, and the reaction times is 10-15h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011103528010A CN103102245A (en) | 2011-11-09 | 2011-11-09 | Preparation method for 1-dibromopyrene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011103528010A CN103102245A (en) | 2011-11-09 | 2011-11-09 | Preparation method for 1-dibromopyrene |
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| CN103102245A true CN103102245A (en) | 2013-05-15 |
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| CN2011103528010A Pending CN103102245A (en) | 2011-11-09 | 2011-11-09 | Preparation method for 1-dibromopyrene |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105973863A (en) * | 2016-07-29 | 2016-09-28 | 齐齐哈尔大学 | Method for detecting benzoic acid through phosphorescence at room temperature |
| CN107434758A (en) * | 2017-05-23 | 2017-12-05 | 浙江工业大学 | Method for synthesizing monobromo condensed ring aromatic hydrocarbon compound |
| CN108299149A (en) * | 2018-03-06 | 2018-07-20 | 棓诺(苏州)新材料有限公司 | The synthetic method of high-purity O LED intermediate 1- bromine pyrenes |
| CN114409517A (en) * | 2021-12-31 | 2022-04-29 | 许昌圣壹新材料科技有限公司 | 2-bromofluorenone and preparation method thereof |
-
2011
- 2011-11-09 CN CN2011103528010A patent/CN103102245A/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| JUAN F.SALELLAS, ET AL.: ""Halogenacion nuclear con dibromodimetilhidantoina parte Ⅲ:hidrocarburos aromaticos policiclicos"", 《ANALES DE LA ASOCIACION QUIMICA ARGENTINA》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105973863A (en) * | 2016-07-29 | 2016-09-28 | 齐齐哈尔大学 | Method for detecting benzoic acid through phosphorescence at room temperature |
| CN105973863B (en) * | 2016-07-29 | 2018-08-14 | 齐齐哈尔大学 | A kind of method of room temperature phosphorimetry detection benzoic acid |
| CN107434758A (en) * | 2017-05-23 | 2017-12-05 | 浙江工业大学 | Method for synthesizing monobromo condensed ring aromatic hydrocarbon compound |
| CN108299149A (en) * | 2018-03-06 | 2018-07-20 | 棓诺(苏州)新材料有限公司 | The synthetic method of high-purity O LED intermediate 1- bromine pyrenes |
| CN108299149B (en) * | 2018-03-06 | 2021-03-02 | 棓诺(苏州)新材料有限公司 | Synthesis method of high-purity OLED intermediate 1-bromopyrene |
| CN114409517A (en) * | 2021-12-31 | 2022-04-29 | 许昌圣壹新材料科技有限公司 | 2-bromofluorenone and preparation method thereof |
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Application publication date: 20130515 |