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CO probe and preparation method and application thereof

A technology of probes and p-nitrobenzene, applied in chemical instruments and methods, analysis by making materials undergo chemical reactions, instruments, etc., can solve the problems of expensive instruments, complicated pre-treatment, inconvenient carrying, etc. Simple processing, easy to obtain products, and high sensitivity

Active Publication Date: 2016-06-01
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Traditional CO monitoring methods include non-dispersive infrared method, dynamic coulometric method, penetrating infrared filter method and gas chromatography, etc. These methods generally have some defects, such as: expensive instruments, complicated pre-treatment, inconvenient to carry, etc.

Method used

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  • CO probe and preparation method and application thereof
  • CO probe and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032] (1) Add 200 mg of chlorop-nitrobenzofuroxan (1.0 mmol) to an acetonitrile solution (15 mL) containing 246L n-propylamine (3.0 mmol), add 300 mg of anhydrous potassium carbonate solid, and stir at room temperature for 1 hour. , Suction filtration, concentration of the filtrate, and column chromatography to obtain 4-propylamino-7-nitro-2,1,3-benzoxoxadiazole (Intermediate 1) with a yield of 64%;

[0033] (2) Dissolve 111mg of Intermediate 1 (0.5mmol) in 10mL of anhydrous acetonitrile, add 412μL of diisopropylethylamine (2.5mmol) under nitrogen protection, stir at room temperature for 0.5 hours, and then add 211μL of allyl chloroformate (2.0mmol) was slowly added dropwise to the above solution, after the dropwise addition was completed, reacted at room temperature for 12 hours, suction filtered, the filtrate was concentrated, and column chromatography was used to obtain 134mg of CO probe (I). The yield was 88%. The synthetic route of the product is as follows figure 1 Shown....

Embodiment 2

[0038] (1) Add 200 mg of chloro-p-nitrobenzofuran (1.0 mmol) to a tetrahydrofuran solution (15 mL) containing 247L of n-propylamine, add 280 mg of anhydrous potassium carbonate, stir at room temperature for 1 hour, and filter with suction. The filtrate Concentrate and column chromatography to obtain 4-propylamino-7-nitro-2,1,3-benzoxoxadiazole (Intermediate 1) with a yield of 60%;

[0039] (2) Dissolve 112mg of Intermediate 1 (0.5mmol) in 10mL of tetrahydrofuran, add 330μL of diisopropylethylamine (2mmol) under nitrogen protection and stir at room temperature, then slowly add 317μL of allyl chloroformate (3.0mmol) Add dropwise to the above solution, after the dropwise addition, react overnight at room temperature, filter with suction, concentrate the filtrate, and column chromatography to obtain CO probe (I). The yield was 82%. product 1 HNMR spectrum and 13 CNMR spectrum and figure 2 with image 3 Consistent; the high-resolution mass spectrum of the product is consistent with ...

Embodiment 3

[0041] (1) Add 2.0g of chlorop-nitrobenzofurazan to a methanol solution (120mL) containing 2.5mL of n-propylamine, add 2.5g of anhydrous potassium carbonate solid, stir at room temperature for 2 hours, filter with suction, and concentrate the filtrate , Column chromatography to obtain 4-propylamino-7-nitro-2,1,3-benzoxoxadiazole (Intermediate 1) with a yield of 47%;

[0042] (2) Dissolve 1.2g of Intermediate 1 in 100mL of acetonitrile, add 3.2mL of diisopropylethylamine under the protection of nitrogen and stir at room temperature, then slowly drop 2.9mL of allyl chloroformate into the above solution, dropwise After the addition is complete, react overnight at room temperature, filter with suction, concentrate the filtrate, and column chromatography to obtain CO probe (I). The yield was 73%. product 1 HNMR spectrum and 13 CNMR spectrum and figure 2 with image 3 Consistent; the high-resolution mass spectrum of the product is consistent with Figure 4 Consistent.

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Abstract

The invention belongs to the technical field of detection materials and discloses a CO probe and a preparation method and application thereof. The CO probe has a structural formula shown as the formula (I). According to the preparation method, chloro-paranitrobenzo furazan is added into an n-propylamine organic solution, then anhydrous potassium carbonate is added, the mixture is stirred at room temperature for a reaction, and the reaction product is subjected to separation and purification to obtain 4-propylamino-7-nitro-2,1,3-benzooxadiazole; 4-propylamino-7-nitro-2,1,3-benzo oxadiazole is dissolved in an anhydrous organic solvent, diisopropylethylamine is added under protection of an inert atmosphere, the mixture is stirred and mixed to be uniform, then allyl chloroformate is added dropwise for a reaction at room temperature, and the reaction product is subjected to separation and purification to obtain the CO probe. Through the preparation method, the process is simple, and operation is easy; the obtained CO probe responds to both ultraviolet and fluorescent light and can be applied to the field of CO detection. (Please see the description for the formula (I).).

Description

Technical field [0001] The invention belongs to the technical field of detection materials, and specifically relates to a CO probe and a preparation method and application thereof. Background technique [0002] CO is considered to be a colorless and odorless killer. When any animal or human inhales a high concentration of CO, it will be killed in a short time, and this gas is odorless and difficult to detect in the natural environment. The water gas or liquefied gas used in modern society may cause the leakage of CO and cause harm to people's lives and property. However, as people continue to study CO, it has been found that CO also has an important regulatory effect on human body functions. It can control liver blood circulation, regulate cardiovascular smooth muscle and its own metabolism. In order to better control the concentration of CO in the gas and detect the concentration of CO in the environment, it is of great significance to study a method with high sensitivity and h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D271/12C09K11/06G01N21/33G01N21/64G01N21/78
CPCC07D271/12C09K11/06C09K2211/1048G01N21/33G01N21/643G01N21/783
Inventor 张雷徐忠勇李晶颜金武
Owner SOUTH CHINA UNIV OF TECH
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