SYNTHESIS AND STUDY OF THE PROPERTIES OF 3-NITRO-3'-AMINOCHALCONE AND ITS AZO DERIVATIVE

M. A. Kulikov

doi:10.55421/3034-4689_2026_29_6_38

SYNTHESIS AND STUDY OF THE PROPERTIES OF 3-NITRO-3'-AMINOCHALCONE AND ITS AZO DERIVATIVE

Published in Herald of Technological University · Pages 38–42 · Rubric: 1. Chemistry

DOI: https://doi.org/10.55421/3034-4689_2026_29_6_38 · EDN: WFYCBY

Received: 19.05.2026 Accepted: 04.06.2026 Published: 02.07.2026

Authors

M. A. Kulikov

Bereznikovskiy filial Permskogo nacional'nogo issledovatel'skogo politehnicheskogo universiteta Russian Federation

ABSTRACT

Chalcones, also known as benzylideneacetophenones and phenylstyryl ketones, belong to an important class of organic molecules whose structural basis is 1,3-diphenylprop-2-en-1-one. Chalcone structural elements are frequently found in various biologically active compounds of natural and synthetic origin. The chalcone molecule has two strong electrophilic centers, which has led to its use in organic synthesis. Chalcones are synthesized primarily using the Claisen-Schmidt reaction, as well as alternative methods. One way to modify the properties of chalcones is to synthesize azo compounds from them. This work is devoted to the study of the properties of 3-nitro-3'-aminochalcone and its azo derivative with 2-hydroxychalcone. Synthesis of 3-nitro-3'-aminochalcone was carried out by the Claisen-Schmidt reaction from 3-aminoacetophenone and 3-nitrobenzaldehyde. The synthesis product after recrystallization from a mixture of DMF and isopropyl alcohol is a yellow solid with a melting point of 148-150 °C. Its structure was determined using FTIR spectroscopy. The optical properties of the compound were studied in DMF and sulfuric acid. The thermal stability limits of the substance were determined using the DTA-TGA results. Its decomposition occurs at temperatures above 280 °C and is accompanied by an exothermic effect. In the next step, the azo compound was synthesized from 3-nitro-3'-aminochalcone and 2-hydroxychalcone. The diazotization and azo coupling reactions were carried out according to general methods for the preparation of azo dyes. After reprecipitation from DMF with water, an orange product was obtained that decomposed at 187-189°C. The structure of the azo compound was determined using Fourier transform IR spectroscopy. The UV-Vis spectra of the product exhibit several absorption bands. These are due to p®p* electronic transitions affecting individual chromophore sites in the molecule.

KEYWORDS

CHALCONE, 3-AMINOACETOPHENONE, 3-NITROBENZALDEHYDE, AZO COMPOUND, CLAISEN-SCHMIDT REACTION, AZO COUPLING REACTION, SPECTRAL RESEARCH METHODS, DTA-TGA

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GOST

Kulikov M. A. SYNTHESIS AND STUDY OF THE PROPERTIES OF 3-NITRO-3'-AMINOCHALCONE AND ITS AZO DERIVATIVE // . 2026. pp. 38-42. DOI: https://doi.org/10.55421/3034-4689_2026_29_6_38. EDN: WFYCBY. (Date of access 20.08.2026).

MLA

M. A. Kulikov. "SYNTHESIS AND STUDY OF THE PROPERTIES OF 3-NITRO-3'-AMINOCHALCONE AND ITS AZO DERIVATIVE." (2026): 38-42. DOI: https://doi.org/10.55421/3034-4689_2026_29_6_38. EDN: WFYCBY.

APA

Kulikov M. A. (2026). SYNTHESIS AND STUDY OF THE PROPERTIES OF 3-NITRO-3'-AMINOCHALCONE AND ITS AZO DERIVATIVE. , 38-42. https://doi.org/10.55421/3034-4689_2026_29_6_38 EDN: WFYCBY.

Chicago

M. A. Kulikov. "SYNTHESIS AND STUDY OF THE PROPERTIES OF 3-NITRO-3'-AMINOCHALCONE AND ITS AZO DERIVATIVE." , no. (2026): 38-42. https://doi.org/10.55421/3034-4689_2026_29_6_38. EDN: WFYCBY.

WIKI

{{cite journal | author = Kulikov M. A. | title = SYNTHESIS AND STUDY OF THE PROPERTIES OF 3-NITRO-3'-AMINOCHALCONE AND ITS AZO DERIVATIVE | journal = | year = 2026 | pages = 38-42 | doi = 10.55421/3034-4689_2026_29_6_38 }} EDN: WFYCBY

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