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O-nitrophenyl azo salicylaldehyde phenoxy acetyl hydrazone, and synthesis and application thereof in CN<-> colorimetric detection

A kind of technology of nitrophenyl azo salicylaldehyde phenoxyacetyl hydrazone, nitrophenyl azo salicylaldehyde, applied in the field of organic chemical synthesis, can solve problems such as expensive, laborious, time-consuming and the like

Inactive Publication Date: 2013-05-22
LANZHOU JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, other methods require expensive instruments and equipment, time-consuming, laborious, and professional operations.

Method used

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  • O-nitrophenyl azo salicylaldehyde phenoxy acetyl hydrazone, and synthesis and application thereof in CN&lt;-&gt; colorimetric detection
  • O-nitrophenyl azo salicylaldehyde phenoxy acetyl hydrazone, and synthesis and application thereof in CN&lt;-&gt; colorimetric detection
  • O-nitrophenyl azo salicylaldehyde phenoxy acetyl hydrazone, and synthesis and application thereof in CN&lt;-&gt; colorimetric detection

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 1. Synthesis of receptor compound: Weigh 270 mg (1 mmol) of o-nitrophenyl azosalicylaldehyde and 166 mg (1 mmol) of phenoxyacetylhydrazine, and mix them in a 50 mL reaction flask; Add 20 mL of absolute ethanol as a solvent, 0.2 mL of glacial acetic acid as a catalyst, heat and reflux in an oil bath at 80°C for 8 h, a precipitate is formed, stand still, filter with suction, and use DMF-C 2 h 5 OH (DMF:C 2 h 5 OH=1:1) recrystallization to obtain the purple target product. Yield: 78%.

[0043] m.p.: 203-205°C. 1 H NMR (DMSO- d 6 , 400 MHz ppm) δ: 12.937 (s. 1H. OH), 10.14 (s. 1H. NH), 8.96 (s. 1H. N=CH), 6.944-6.987 (m. 4H. Ar–CH); IR (KBr, cm -1 ) ν: 1602(C=N); 1186(C=S); 2980(N=C–H); 3445(N–H). MS / (EI): m / z 420.2(M+H) + . Anal. Calc. for C 21 h 17 N 5 o 5 : C, 59.97; H, 4.05; N, 16.66. Found: C, 59.88; H, 4.12; N, 16.45.

[0044] 2. Production of test paper

[0045] Soak the filter paper in dilute hydrochloric acid with a mass concentration of 9.5-10% for ...

Embodiment 2

[0049] 1. Synthesis of acceptor compound: Weigh 270 mg (1 mmol) of o-nitrophenylazosalicylaldehyde and 332 mg (2 mmol) of phenoxyacetylhydrazine, and mix them in a 100 mL reaction flask; Add 50 mL of absolute ethanol as a solvent, 0.5 mL of glacial acetic acid as a catalyst, heat and reflux in an oil bath at 75°C for 8 h, a precipitate is formed, stand still, filter with suction, and use DMF-C 2 h 5 OH (DMF:C 2 h 5 OH=1:2) recrystallization to obtain the purple target product. Yield: 79%.

[0050] 2, the making of detection test paper: with embodiment 1.

[0051] 3. Test paper test CN － : with embodiment 1.

Embodiment 3

[0053] 1. Synthesis of acceptor compound: Weigh 270 mg (1 mmol) of o-nitrophenylazosalicylaldehyde and 249 mg (1.5 mmol) of phenoxyacetylhydrazine, and mix them in a 100 mL reaction flask; Add 50 mL of absolute ethanol as a solvent, 0.3 mL of glacial acetic acid as a catalyst, heat and reflux in an oil bath at 80°C for 7 h, a precipitate forms, stand still, filter with suction, and use DMF-C 2 h 5 OH (DMF:C 2 h 5 OH=1:1.5) recrystallization to obtain the purple target product. Yield: 76%.

[0054] 2, the making of detection test paper: with embodiment 1.

[0055] 3. Test paper test CN － : with embodiment 1.

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Abstract

The invention discloses an o-nitrophenyl azo salicylaldehyde phenoxy acetyl hydrazone compound. According to the o-nitrophenyl azo salicylaldehyde phenoxy acetyl hydrazone compound, the compound is prepared through taking anhydrous ethanol as a solvent, glacial acetic acid as a catalyst and o-nitrophenyl azo salicylaldehyde and phenoxy acethydrazide as reaction substrates, carrying out reflux reaction until precipitates are produced, standing, and carrying out suction filtration and recrystallization; the role of the compound in recognition on negative ions, such as F<->, Cl<->, Br<->, I<->, CH3COO<->, H2PO4<->, HSO4<->, ClO4<-> and CN<->, is inspected through ultraviolet-visible absorption spectrum, colorimetric recognition and <1>HNMR titration; and shown by results, the compound can carry out high-selectivity colorimetric recognition on CN<-> in a DMSO (Dimethyl Sulfoxide) water-bearing system. CN<-> detection test paper manufactured based on a receptor, namely the compound, can be used for detecting cyanogens ions conveniently and fast. Thus, receptors of the type have a certain potential application value in the colorimetric detection on CN<-> in water-bearing systems.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and relates to an acylhydrazone compound and a synthesis method thereof, in particular to an o-nitrophenylazosalicylaldehyde phenoxyacetylhydrazone compound and a synthesis method thereof; Hydrazone Compounds as Acceptor Molecules in Colorimetric Detection for Recognition of CN － in the application. Background technique [0002] The research on cyanide chemical sensors is one of the most active research fields in supramolecular chemistry. Cyanide is an important raw material for synthetic resins, medicines, pesticides, insecticides, fertilizers, etc. It is also an important reagent for gold plating and metallurgy, and is highly toxic. The lethal dose to human is very small. In addition to direct ingestion, its vapor and dust can also enter the human body through the respiratory tract or digestive tract, and even penetrate into the skin and Fe in cytochrome oxidase in the body. 3+ Combi...

Claims

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Application Information

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IPC IPC(8): C07C251/86C07C249/16G01N21/31G01N21/33G01N21/79
Inventor 胡京汉颜农平陈娟娟李建斌
Owner LANZHOU JIAOTONG UNIV
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