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Water-soluble triazine derivatives as well as preparation method and uses thereof

A s-triazine and water-soluble technology, which is applied in the field of water-soluble s-triazine derivatives and its preparation and application, to improve the separation effect, increase the separation ability, and achieve the effect of size separation

Inactive Publication Date: 2008-08-27
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the halogenated-s-triazine derivatives used as labeling reagents generally have no water-soluble groups, and the derivatization reaction should be used in the organic phase

Method used

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  • Water-soluble triazine derivatives as well as preparation method and uses thereof
  • Water-soluble triazine derivatives as well as preparation method and uses thereof
  • Water-soluble triazine derivatives as well as preparation method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1, the preparation of water-soluble halogenated s-triazine derivative (5)

[0028]

[0029] The reaction process is represented by the following reaction scheme:

[0030]

[0031] 2,5-Disulfonateaniline monosodium salt (16.5 g) was dissolved in 100 mL of NaOH (2.4 g) solution, and 40 g of crushed ice was added. Added hot acetone (10mL) solution of cyanuric chloride (5.5g) under the condition of vigorous stirring, reacted in ice-water bath for 1h, the temperature rose to 50°C, continued to react for 12h, added 20% NaOH solution during the reaction to make the reaction solution Keep it close to neutral. After the reaction, NaCl was added to precipitate the product 2-chloro-4,6-bis-(2,5-disulfonic acid aniline)-1,3,5-triazine (3), filtered and washed with 25% NaCl solution Cake 3 times, dry.

[0032] An aqueous solution (100 mL) of 2-chloro-4,6-bis-(2,5-disulfonateaniline)-1,3,5-triazine (3) (14.1 g) was added to phenylenediamine hydrochloride Salt (5....

Embodiment 2

[0033] Embodiment 2, the preparation of water-soluble chlorotriazine derivative (11)

[0034]

[0035] The reaction process is represented by the following reaction scheme:

[0036]

[0037] 2-Amino-5-hydroxy-1,7-naphthalenedisulfonic acid (16.0 g) was dissolved in 100 mL of NaOH (4 g) solution, and 100 g of crushed ice was added. In an ice-water bath, slowly add a solution of cyanuric chloride (4.58g) in hot acetone (10mL) under vigorous stirring. During the addition, use 20% NaOH solution to adjust the pH to 3, and react at this pH for 1h. The temperature was raised to 55° C., and the reaction was continued for 5 h. During the reaction, 20% NaOH solution was added to make the pH value of the reaction solution about 5. After the reaction, add NaCl to precipitate the product, filter, wash the filter cake with 25% NaCl solution, and dry.

[0038] Under stirring, 40 ml of a mixed solution of sodium nitrite (2.07 g) and sodium aniline-2,5-disulfonate (7 g) was added dropwis...

Embodiment 3

[0040] Embodiment 3, preparation of water-soluble chlorinated-s-triazine derivative (15)

[0041]

[0042] The reaction process is represented by the following reaction scheme

[0043]

[0044] The synthesis of 2-chloro-4,6-bis-(2,5-disulfonic acid aniline)-1,3,5-triazine (3) is as in Example 1.

[0045] An aqueous solution (60 mL) of 2-chloro-4,6-bis-(2,5-disulfonateaniline)-1,3,5-triazine (3) (14.1 g) was added to ethylenediamine hydrochloride In the salt (0.03mol) water (30mL) solution, 85 ° C water bath for 5h, during the reaction, add 20% NaOH solution to keep the reaction solution nearly neutral. The product (13) was precipitated by adding NaCl, filtered, washed and dried.

[0046] In an ice-water bath, add a hot acetone (5 mL) solution of cyanuric chloride (1.83 g) to an ice-cold (13) (7.5 g) aqueous solution under vigorous stirring, react in an ice bath, and adjust the pH with 20% NaOH The value is equal to 4, and the temperature rises to 55° C. after 2 hours....

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Abstract

The invention discloses a soluble triazine derivative, a relative preparation method and an application, wherein the soluble triazine derivative is represented as formula I, X is chromogenic group with ultraviolet adsorption, fluorescence chromogenic or chemilumienscence activity Y is provided with soluble group and Z is provided with reaction active group. The soluble triazine derivative leads in different active groups, thereby marking and analyzing different compounds, and leads in many water dissociation groups, thereby applying for the mark and analysis which uses water as medium and particularly applying for the mark and analysis of life related material as protein, glucose and glycoconjugate or the like.

Description

technical field [0001] The invention relates to a water-soluble s-triazine derivative, a preparation method and application thereof. Background technique [0002] Halogenated-s-triazines are very important synthetic intermediates, widely used in the synthesis and preparation of pesticides, dyes, fluorescent whitening agents, etc. In analytical chemistry, halogenated-s-triazines are often used as bridging agents for the synthesis of optically labeled probes, photosensitive sensors, chromatographic stationary phases, and adsorbents. Most of them retain one or two halogen atoms as active atoms for labeling or fixing during the preparation process, which limits their application range to some extent. There are also researchers who replace three halogen atoms with different groups. For example, Kempter et al. made cyanuric chloride react with 1-methoxynaphthylamine and dimethylamine in turn, and then converted the third chlorine into a hydrazine group to prepare A fluorescent r...

Claims

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Application Information

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IPC IPC(8): C07D251/54G01N21/00
Inventor 陈义郭振朋齐莉
Owner INST OF CHEM CHINESE ACAD OF SCI
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