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Gem-difluoromethylene-containing azo compound and preparation method thereof

A technology of difluoromethylene azo and sodium difluoromethane sulfinate, applied in directions such as organic chemistry, can solve the problems such as the synthetic method of geminal difluoromethylene has not yet been reported, and achieves good tolerance, The effect of mild reaction conditions and easy operation

Active Publication Date: 2019-10-11
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, azo compounds containing gem-difluoromethylene groups and their synthetic methods have not been reported

Method used

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  • Gem-difluoromethylene-containing azo compound and preparation method thereof
  • Gem-difluoromethylene-containing azo compound and preparation method thereof
  • Gem-difluoromethylene-containing azo compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0277] Example 1: Under nitrogen protection, copper sulfate (0.05mmol), TsOH (0.35mmol), tetrafluoroborate-4-methoxyphenyldiazonium salt (0.6mmol) were added successively in a 10ml reaction tube equipped with magnetons ), 1,3-benzoxazole-2-difluoromethanesulfinate sodium (2.0mmol), DCM 2.5ml, TBHP (4.0mmol) was added dropwise at 50°C with stirring. The reaction was stopped after 10 h, and the solid in the reaction solution was filtered through a short column of silica gel and concentrated. The crude product was separated and purified by column chromatography to obtain the target product 3p with a yield of 88%.

Embodiment 2

[0278] Example 2: Under nitrogen protection, add cuprous iodide (0.07mmol), trifluoroacetic acid (0.25mmol), and tetrafluoroborate-4-ethanonephenyldiazonium salt in sequence in a 10ml reaction tube equipped with magnetons (0.5mmol), sodium 1,3-benzoxazole-2-difluoromethanesulfinate (2.0mmol), Dioxane 4ml, TBHP (3.5mmol) was added dropwise at 20°C with stirring. The reaction was stopped after 8 h, and the solid in the reaction solution was filtered through a short column of silica gel and concentrated. The crude product was separated and purified by column chromatography to obtain the target product 3b with a yield of 86%.

Embodiment 3

[0279] Embodiment three: under nitrogen protection, silver acetate (0.5mmol), hydrochloric acid (2.5mmol), tetrafluoroboric acid-4-benzophenone phenyl diazonium salt (1.0mmol) were added successively in a 20ml reaction tube equipped with magnetons ), 1,3-benzoxazole-2-sodium difluoromethanesulfinate (3.5mmol), dimethylformamide 6.0ml, reaction stirring at room temperature and adding TBHP (6mmol) dropwise. The reaction was stopped after 10 h, and the solid in the reaction solution was filtered through a short column of silica gel and concentrated. The crude product was separated and purified by column chromatography to obtain the target product 3c with a yield of 23%.

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Abstract

The invention relates to azo compounds containing gem-difluoro methylene and a preparation method of the azo compounds. The structural formula of the azo compounds is shown in the specification, wherein X is O, S and N-Bu; and Ar is shown in the specification, wherein R is an aldehyde group, halogen, ethyl carbonyl, a cyano group, nitro, trifluoromethyl or methyl. According to the azo compounds containing the gem-difluoro methylene and the preparation method of the azo compounds, coupled reaction is conducted between 1,3-benzoxadiazole-2-difluromethyl sulfinic acid sodium and tetrafluoride boronaromatic diazonium salt under promoting of transition metal salt, and the series of azo compounds containing the gem-difluoro methylene are generated; the raw materials are easy to get; operation is easy and convenient; the reaction condition is mild; and the azo compounds have good tolerance on active groups.

Description

technical field [0001] The invention relates to a series of azo compounds containing gem-difluoromethylene groups and a preparation method thereof. Background technique [0002] The azo compound refers to an organic compound containing an azo group (-N=N-) in the molecular structure. Aromatic azo compounds usually have strong absorption in the ultraviolet and visible light regions and have special optical properties. They can be used as dyes or pigments in textiles, food additives, color liquid crystal displays and color photographic films. Aliphatic azo compounds are relatively sensitive to light, heat, etc., and are usually used as photoresists or photoinitiators. Because azo compounds -N=N- have the properties of cis-trans isomerization and have photochromic properties, so that azo compounds have specific optical and electrical properties, and can be used as optical information storage materials, so azo compounds have been used Become one of the indispensable materials ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/12C07D417/12C07D263/56C07D277/64
Inventor 蒋海珍王得晶陈波许辉万文郝建
Owner SHANGHAI UNIV