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A kind of reagent for distinguishing and detecting thiophenol and its synthesis method and application

A synthesis method and detection reagent technology, which are applied in the synthesis method of benzothiazole derivatives and its application in distinguishing and detecting thiophenols, can solve the problems of central nervous system damage, hindlimb paralysis, coma, etc., and achieve response time Short, strong specificity, obvious effect of detection signal

Active Publication Date: 2022-05-20
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, long-term activities in water, soil, air and other environments containing thiophenol can lead to a series of serious health problems, including damage to the central nervous system, shortness of breath, muscle weakness, paralysis of hind limbs, coma, and even death

Method used

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  • A kind of reagent for distinguishing and detecting thiophenol and its synthesis method and application
  • A kind of reagent for distinguishing and detecting thiophenol and its synthesis method and application
  • A kind of reagent for distinguishing and detecting thiophenol and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Preparation and characterization of SYN

[0033] In a 50 mL round bottom flask, 2-aminothiophenol (5 mmol, 0.625 g) and 5-methylsalicylaldehyde (5 mmol, 0.681 g) were added to 15 mL of DMSO, and silver nitrate (0.05 mmol, 0.009 g ) with stirring, the mixture was reacted at room temperature in the dark for 2 hours. After the reaction was completed, it was diluted 3 times with dichloromethane (50 mL), washed with brine, the organic phases were combined, dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (ethyl acetate / petroleum ether=1:6 ) to obtain the compound as a pale yellow solid (0.893 g, 74.07%), which is 2-benzothiazol-2-yl-4-methylphenol. 1 H NMR (600MHz, Chloroform-d) δ8.01(d, J=8.1Hz, 1H), 7.93(d, J=7.9Hz, 1H), 7.56-7.48(m, 2H), 7.43(t, J= 7.5Hz, 1H), 7.21(d, J=8.3Hz, 1H), 7.04(d, J=8.4Hz, 1H), 2.37(s, 3H). 13 C NMR (150MHz, Chloroform-d) δ 169.41, 155.79, 151.84, 133.79, 132.60, 128.72, 128.34, 126.67, 125.47, 122.12, 12...

Embodiment 2

[0038] Prepare CH 3 OH / CH 3 CN / Hepes (10mM) (1:1:1, v / v / v, pH=7.4) solution, prepare 2mMSYN DMSO solution, prepare 0.2mM p-methylthiophenol acetonitrile solution; take 2mL CH 3 OH / CH 3 CN / Hepes (1:1:1, v / v / v, pH=7.4) solution and 10 μL SYN DMSO solution were added to a fluorescent cuvette, and the aqueous solution of p-methylthiophenol was gradually added with a small amount of Add the sample device into the cuvette, and detect it on the fluorescence spectrophotometer while adding the sample. With the addition of p-methylthiophenol, the fluorescence intensity at 686nm gradually increases. Fluorescence emission map see Figure 4 .

Embodiment 3

[0040] Prepare CH 3 OH / CH 3 CN / Hepes (10mM) (1:1:1, v / v / v, pH=7.4) solution, prepare 2mMSYN DMSO solution, prepare 2mM p-methylthiophenol acetonitrile solution; in the fluorescence cuvette, each Add 2 mL of CH 3 OH / CH 3 CN / Hepes (1:1:1, v / v / v, pH=7.4) solution and 10 μL SYN DMSO solution, and then add 10 times the equivalent of other analytes (1) Cys, (2) Hcy, (3) GSH,(4)SO 3 2- , (5)S 2- , (6)F - , (7)Cl - , (8)OAc - , (9)I - , (10) aniline, (11) aqueous solution of phenol, and acetonitrile solution of 2 times equivalent thiophenol homologue (12) 4-aminothiophenol (20 μ M), (13) thiophenol (20 μ M) and (14 ) 4-methylthiophenol (20 μM). Detect on a fluorescence spectrophotometer, and draw a histogram of fluorescence intensity at 686nm corresponding to different analytes (see Figure 5 ). p-cresol, p-amino-thiophenol, and thiophenol can significantly increase the fluorescence intensity of the detection system at 686nm, and other analytes basically do not cause chan...

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Abstract

The invention provides a reagent for distinguishing and detecting thiophenol and its synthesis method and application. The reagent is a benzothiazole derivative: the Chinese name of the derivative is (E)‑2‑(benzo Thiazol-2-yl)-6-(2-(3-(dicyanomethylene)-5,5-dimethylcyclohex-1-en-1-yl)vinyl)-4-methyl Phenyl 2,4-dinitrobenzenesulfonate, the English name is (E)-2-(benzothiazol-2-yl)-6-(2-(3-(dicyanomethylene)-5,5-dimethylcyclohex-1 ‑en‑1‑yl)vinyl)‑4‑me thylphenyl 2,4‑dinitrobenzenesulfonate, named SYN. The detection method is Hepes‑CH at pH 7.4 3 OH‑CH 3 In the buffer solution of CN (1:1:1, v / v / v), the content of thiophenol was quantitatively detected by fluorescence spectrophotometer. The detection process is simple, sensitive and fast, and the detection result is accurate.

Description

technical field [0001] The invention relates to the detection of thiophenol, in particular to a synthesis method of benzothiazole derivatives and its application in distinguishing and detecting thiophenol. Background technique [0002] Thiophenol plays an important role in organic synthesis and is widely used in the preparation of agrochemicals, pharmaceuticals and various industrial products. However, thiophenols are more toxic than aliphatic thiols. The average lethal dose (LC50) of thiophenols in fish is 0.01-0.4mM. In addition, long-term activities in water, soil, air and other environments containing thiophenol can lead to a series of serious health problems, including damage to the central nervous system, shortness of breath, muscle weakness, paralysis of hind limbs, coma, and even death. In view of the above existing problems, it is very meaningful to design fluorescent probes with good selectivity, high sensitivity, and low cytotoxicity for the differential detecti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/66C09K11/06G01N21/64
CPCC07D277/66C09K11/06G01N21/643C09K2211/1037C09K2211/1007
Inventor 任海仙阴彩霞霍方俊
Owner SHANXI UNIV
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