A method for preparing 5-fluorescein isothiocyanate
A technology of fluorescein isothiocyanate and fluorescein, which is applied in organic chemistry and other fields, can solve the problems of high thiophosgene price, strong odor, and high production risk, and achieve high process operation safety and simple synthesis process , the effect of mild reaction conditions
Active Publication Date: 2019-04-02
SUZHOU BAILINGWEI HYPERFINE MATERIAL
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Problems solved by technology
[0005] This method has two very obvious disadvantages: first, the thiophosgene used is very toxic and has a very strong smell, and the safety of the process operation is very poor; second, the price of thiophosgene is relatively high, and the price per kilogram is 3000 More than RMB 1,000, and it is inconvenient to purchase, resulting in high production cost of 5-fluorescein isothiocyanate
The synthesis process is dangerous to produce, and the production cost is high, so it is not suitable for the needs of industrial production
[0006] In view of the fact that the current technology for preparing 5-fluorescein isothiocyanate has the problems of high production risk and high production cost, it is very important to find a kind of industrial production method for green synthesis of 5-fluorescein isothiocyanate significance
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example 1
[0039] The method for preparing 5-fluorescein isothiocyanate described in this embodiment comprises the following steps:
[0040] Step 1: Preparation of triethylammonium salt of fluorescein-5-dithiocarbamate, the chemical reaction formula is:
[0041]
[0042] Under stirring at room temperature, 20 L of tetrahydrofuran and 6.95 Kg of 5-aminofluorescein were sequentially added into the 50 L reaction kettle. Then it was cooled to 0° C., and 6.07 Kg of triethylamine was added dropwise thereto, and the dropwise was completed in 1 hour. The reaction system was slightly exothermic during the dropwise addition. After the triethylamine was dropped, 1.53Kg of carbon disulfide was added dropwise therein, and the drop was completed in 30 minutes. During the dropwise addition, the reaction system exothermic was relatively obvious. After dropping, keep the reaction at 0°C for 2 hours, then raise the temperature to 30°C and continue the reaction for 2 hours, and the reaction ends.
[0...
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The invention provides a method for preparing 5-fluorescein isothiocyanate ester. The method comprises the following steps: (1) reacting an original material 5-amino fluorescein with carbon disulfide in the presence of a catalyst and a solvent, so as to obtain fluorescein-5-amine disulfide formate; and (2) reacting fluorescein-5-amine disulfide formate, obtained in the step (1), in the presence of the catalyst and the solvent, so as to obtain 5-fluorescein isothiocyanate ester. The method has the beneficial effects that the technical operational safety is relatively high, the production cost is low, a synthetic process is simple, and the reaction condition is mild; and 5-fluorescein isothiocyanate ester is high in yield and wide in application range and can adequately meet the requirements of industrial production of products.
Description
technical field [0001] The present invention relates to a method for preparing fluorescein 5-isothiocyanate. Background technique [0002] 5-fluorescein isothiocyanate (5-FITC) is one of the most widely used fluorescent labeling reagents. Its maximum absorption wavelength is 490-495nm, and its maximum emission wavelength is 525-530nm, showing bright yellow-green fluorescence that is very convenient for human eyes to observe. 5-fluorescein isothiocyanate can bind to various antibody proteins, and the bound antibody does not lose its specificity of binding to a certain antigen, and has strong yellow-green fluorescence in alkaline solution. The corresponding antigens can be detected qualitatively, localized or quantitatively by observing under a fluorescent microscope or analyzing by flow cytometry. 5-fluorescein isothiocyanate is also used in medicine, agronomy and animal husbandry, etc., for rapid diagnosis of diseases caused by bacteria, viruses and parasites. [0003] Th...
Claims
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IPC IPC(8): C07D493/10
CPCC07D493/10
Inventor 龙韬习文兵邹增龙
Owner SUZHOU BAILINGWEI HYPERFINE MATERIAL