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Preparation method of sulfonyl chloride compound taking carbazole as fluorogen

A technology of sulfonyl chlorides and compounds, which is applied in the field of synthesis of fluorescent molecular probes, can solve problems such as easy hydrolysis, insufficient detection sensitivity, and deviation of detection results, and achieve good material stability, reasonable process steps, and enhanced conjugation Effect

Inactive Publication Date: 2014-01-01
YANGZHOU UNIV
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Problems solved by technology

[0003] (1) Most labeling reagents are sensitive to moisture in the air, and are easily hydrolyzed during the derivatization reaction, and their hydrolyzed products will interfere with the derivative products to a certain extent
[0004] (2) Some labeling reagents have insufficient detection sensitivity due to their own structure, so that trace compounds cannot be detected
[0005] (3) The derivative products formed when certain labeling reagents undergo derivatization reactions with alcohols and amines have low stability, which affects subsequent detection and analysis, and even causes serious deviations in detection results
[0006] (4) Some labeling reagents are inherently toxic, or produce some toxic substances and corrosive gases after derivatization with the sample

Method used

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  • Preparation method of sulfonyl chloride compound taking carbazole as fluorogen
  • Preparation method of sulfonyl chloride compound taking carbazole as fluorogen
  • Preparation method of sulfonyl chloride compound taking carbazole as fluorogen

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Embodiment Construction

[0032] One, the synthetic steps of 3,6-dimethoxy-9-phenylcarbazole-1-sulfonyl chloride:

[0033] 1. Add 1.00 g carbazole, 16 g silica gel, 2.14 g N-bromosuccinimide and 50 mL dichloromethane into a 100 mL round bottom flask with magnetic stirring, and stir at room temperature for 10 hours. Then suction filter, purify, then add appropriate amount of distilled water and extract with ethyl acetate several times, and spin evaporate the solvent under reduced pressure, then recrystallize the solid with absolute ethanol, filter and dry to obtain 3,6-dibromocarbazole.

[0034] 2. Put a 100 mL round-bottomed flask with magnetic stirring in an ice-water bath, add 0.85 g of sodium to it after argon protection, and slowly drop 10 mL of anhydrous methanol into it. When the metal sodium is completely dissolved to form sodium methoxide, Then add 0.6 g of 3,6-dibromocarbazole, 1.48 g of cuprous iodide, 20 mL of anhydrous N,N-dimethylformamide, heat and reflux for 4 hours, stop the heating, co...

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Abstract

The invention discloses a sulfonyl chloride compound taking carbazole as a fluorogen and a preparation method and applications thereof, and relates to the technical field of alcohol and amine substance detection in the fields of environment, medicine, food and sanitation. Precursor compounds such as carbazole, N-bromo-succinimide, sodium methoxide, iodobenzene, chlorosulfonic acid and thionyl chloride are used as raw materials for preparing a new sulfonyl chloride compound taking the carbazole as a fluorescent matrix ring. The sulfonyl chloride compound disclosed by the invention can be used as a fluorescent molecular probe for detecting the alcohol and amine substances in the fields of environment, medicine, food and sanitation, and can also be used as a marking reagent for disease diagnosis and quality monitoring.

Description

technical field [0001] The invention relates to the technical field of detection of alcohols and amines in the fields of environment, medicine, food and sanitation, in particular to the synthesis technology of fluorescent molecular probes for detection. Background technique [0002] At present, there have been many reports on the analysis of alcohols and amines without chromophoric groups using pre-column derivatization reagents, and fluorescent derivatization reagents developed and designed for trace analysis have also been reported one after another. In the preparation of these labeling reagents, most of the products are improved on the existing preparation methods or prepared according to the existing methods and applied to the pre-column derivatization research of high performance liquid chromatography. In addition, most labeling reagents have certain limitations in application, specifically in: [0003] (1) Most labeling reagents are sensitive to moisture in the air, a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/88G01N21/64G01N30/06
Inventor 王赪胤张毅袁宇胡效亚
Owner YANGZHOU UNIV
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