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Arylboronic acid derivatives and preparation method thereof

A technology of aryl boronic acid and derivatives, applied in the field of aryl boronic acid derivatives and their preparation, can solve problems such as insufficient environmental protection of organic flame retardants, and achieve the effect of solving high toxicity

Active Publication Date: 2013-10-30
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to solve the defects of insufficient environmental protection of existing organic flame retardants, and expand the types and application fields of boric acid derivatives, the present invention provides two kinds of aryl boric acid derivatives and their preparation methods

Method used

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  • Arylboronic acid derivatives and preparation method thereof
  • Arylboronic acid derivatives and preparation method thereof
  • Arylboronic acid derivatives and preparation method thereof

Examples

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Effect test

Embodiment 1 3

[0022] Example 1 Preparation of Tris(4,4',4"-triboronic acid-phenyl)amine (3BzN-3B)

[0023] In the first step, under the protection of nitrogen, add n-butyllithium dropwise to the tetrahydrofuran solution of tris(4,4',4"-tribromo-phenyl)amine, control the reaction temperature at -78°C, stir for 1 hour, and then rise to Stir at room temperature for 45 minutes;

[0024] In the second step, the temperature of the reaction liquid obtained in the first step is lowered to -78 ° C, and trimethyl borate is added dropwise therein, stirred for 45 minutes, then warmed up to room temperature and stirred for about 10 hours;

[0025] In the third step, a rotary evaporator is used to remove tetrahydrofuran and unreacted trimethyl borate in the reaction liquid of the second step to obtain a solid product. Dissolve the solid product with dichloromethane, then add saturated aqueous ammonium chloride for extraction, collect the organic phase, dry with anhydrous sodium sulfate and filter, and r...

Embodiment 2 3

[0031] Example 2 Preparation of Tris(4,4',4"-triboronic acid-phenyl)amine (3BzN-3B)

[0032] In the first step, under the protection of nitrogen, add n-butyllithium dropwise to the tetrahydrofuran solution of tris(4,4',4"-tribromo-phenyl)amine, control the reaction temperature at -78°C, stir for 2 hours, and then rise to Stir at room temperature for 36 minutes;

[0033] In the second step, the temperature of the reaction liquid obtained in the first step is lowered to -78°C, and trimethyl borate is added dropwise thereto, stirred for 55 minutes, then warmed up to room temperature and stirred for about 10 hours;

[0034] In the third step, a rotary evaporator is used to remove tetrahydrofuran and unreacted trimethyl borate in the reaction liquid of the second step to obtain a solid product. Dissolve the solid product with dichloromethane, then add saturated aqueous ammonium chloride for extraction, collect the organic phase, dry with anhydrous sodium sulfate and filter, and re...

Embodiment 3 3

[0036] Example 3 Preparation of Tris(4,4',4"-triboronic acid-phenyl)amine (3BzN-3B)

[0037] In the first step, under the protection of nitrogen, add n-butyllithium dropwise to the tetrahydrofuran solution of tris(4,4',4"-tribromo-phenyl)amine, control the reaction temperature at -78°C, stir for 3 hours, and then rise to Stir at room temperature for 30 minutes;

[0038] In the second step, the temperature of the reaction liquid obtained in the first step is lowered to -78 ° C, and trimethyl borate is added dropwise therein, stirred for 80 minutes, then warmed up to room temperature and stirred for about 10 hours;

[0039] In the third step, a rotary evaporator is used to remove tetrahydrofuran and unreacted trimethyl borate in the reaction liquid of the second step to obtain a solid product. Dissolve the solid product with dichloromethane, then add saturated aqueous ammonium chloride for extraction, collect the organic phase, dry with anhydrous sodium sulfate and filter, and ...

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Abstract

The invention provides arylboronic acid derivatives and a preparation method thereof. The two arylboronic acid derivatives are tri(4,4',4'-triboric acid-phenyl)amino(3BzN-3B) and tri(4,4',4'-triboric acid-phenyl)boron(3BzB-3B), and the molecular structures are as shown in the specification. 3BzN-3B and 3BzB-3B are prepared by firstly, respectively reacting tri(4,4',4'-triboric acid-phenyl)amino and tri(4,4',4'-triboric acid-phenyl)boron with n-butyllithium, secondly, respectively carrying out nucleophilic substitution reaction with boric acid ester, and finally carrying out acidolysis by using diluted hydrochloric acid. The products of the arylboronic acid derivatives, namely, the 3BzN-3B and the 3BzB-3B are expected to be excellent environment-friendly organic fire retardants.

Description

technical field [0001] The invention relates to the technical field of flame retardancy of organic polymer materials, in particular to arylboronic acid derivatives and a preparation method thereof. Background technique [0002] With the development of modern science and technology, polymer materials have played a huge role in the national economy and people's lives. Due to the flammability of polymer materials, fire accidents have increasingly become a social issue of concern to people, so flame retardants continue to develop with the development of polymer materials. As the most active field of flame retardants, organic flame retardants have a wide variety, including halogenated flame retardants, organophosphorus flame retardants, etc., but because of their shortcomings such as large smoke generation, high toxicity, and poor thermal stability , so it is imperative to seek new flame retardants. [0003] In view of the fact that boronic acid derivatives are a class of excel...

Claims

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Application Information

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IPC IPC(8): C07F5/02
Inventor 刘平王美晓彭朝阳
Owner SOUTH CHINA UNIV OF TECH
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