2,2'-bis(2-hydroxy-4-sulfonic-1-naphthylamine azoxyl)-5,5'-dimethyl-4,4'-bithiazole and preparation method thereof

A naphthylaminoazo and dimethyl technology, which is applied in the field of diheterocyclic triazene compounds, can solve the problems of fluorescence detection of few metal ions, and the selectivity and sensitivity need to be improved, and achieves a simple preparation method and high sensitivity. , the effect of high sensitivity

Inactive Publication Date: 2013-10-30
SHANXI DATONG UNIV
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Problems solved by technology

However, the selectivity and sensitivity need to be improved, and it is often only used as a chromogenic reagent for photometric analysis, and is rarely used as a fluorescent reagent for the fluorescence detection of metal ions.

Method used

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  • 2,2'-bis(2-hydroxy-4-sulfonic-1-naphthylamine azoxyl)-5,5'-dimethyl-4,4'-bithiazole and preparation method thereof
  • 2,2'-bis(2-hydroxy-4-sulfonic-1-naphthylamine azoxyl)-5,5'-dimethyl-4,4'-bithiazole and preparation method thereof
  • 2,2'-bis(2-hydroxy-4-sulfonic-1-naphthylamine azoxyl)-5,5'-dimethyl-4,4'-bithiazole and preparation method thereof

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Embodiment 1

[0038] 2, 2'-bis(2-hydroxy-4-sulfonic acid-1-naphthylaminoazo)-5, 5' - Dimethyl-4, 4' - Bithiazole, its molecular structural formula:

[0039]

[0040] 2, 2'-bis(2-hydroxy-4-sulfonic acid-1-naphthylaminoazo)-5, 5' - Dimethyl-4, 4' - The preparation method of bithiazole comprises the following steps:

[0041] (1) Preparation of 2,5-dibromohexanedione

[0042] Add 28.5g (0.25mol) 3,4-hexanedione, 45mL chloroform and 10mL glacial acetic acid into a 250mL three-neck flask equipped with a magnetic stirrer dropping funnel and a reflux device, stir and heat to about 80°C on an oil bath , Slowly drop the mixture of 80g liquid bromine and 30mL chloroform from the separatory funnel, and the reaction starts immediately. After the bromine is added dropwise, continue heating until the solution turns from brown-red to orange-yellow, then quickly cool it to 0°C in an ice bath, and yellow needle-like precipitates appear, filter with suction, and recrystallize with chloroform to o...

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Abstract

The invention relates to a bis-heterocyclic triazene compound, and specifically relates to a 2,2'-bis(2-hydroxy-4-sulfonic-1-naphthylamine azoxyl)-5,5'-dimethyl-4,4'-bithiazole and a preparation method thereof. The preparation method comprises the following steps of: (1) preparation of 2,5-dibromohexanedione; (2) preparation of 2,2'-diamino-5,5'-dimethyl-4,4'-bithiazole; (3) preparation of 5,5'-dimethyl-4,4'-bithiazole-2,2'- bis-diazonium salt; (4) preparation of an objective product BHSNAADMBT. The technical scheme of the invention connects bithiazole heterocycle and naphthalene ring derivative with fluorescence property together to synthesize a reagent with double functional-analytical groups and large steric hindrance; and the compound of the invention not only has high reaction sensitivity with metal ions, but also has good selectivity. The reagent is a good photometric analysis developer and a novel fluorescence analytical reagent with high sensitivity and good selectivity as well.

Description

technical field [0001] The present invention relates to a bis-heterocyclic triazene compound, specifically 2, 2'-bis(2-hydroxyl-4-sulfonic acid group-1-naphthylaminoazo)-5,5' - Dimethyl - 4, 4' - Bithiazole and its preparation method. Background technique [0002] Triazene reagent is an excellent color developer for photometric analysis of silver, cadmium, mercury, nickel, copper and other metal ions (Teng Enjiang, Jiang Wanquan, Zhu Yurui, etc., Chemical Reagents, 1992, 14 (2): 109). Because of its -N=N-NH- functional group, -NH- has strong acidity due to p-π conjugation. Under alkaline conditions, it is easy to coordinate with transition metal ions after deprotonation, and it is a good coordination group. This kind of reagent has the advantages of high sensitivity and easy synthesis, and has attracted people's attention. However, the selectivity and sensitivity need to be improved, and it is often only used as a chromogenic reagent for photometric analysis, and is ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/50C09K11/06C09B26/06G01N21/78G01N21/64
Inventor 王君玲张殿龙樊月琴王科伟贾治芳
Owner SHANXI DATONG UNIV
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