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Usage

Uses

Used in Pharmaceutical Industry:
4,5-dibromobenzene-1,2-dicarbonitrile is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to form carbon-carbon bonds and contribute to the creation of complex molecular structures that are vital for drug development.
Used in Agrochemical Industry:
In the agrochemical sector, 4,5-dibromobenzene-1,2-dicarbonitrile is utilized as a precursor in the production of pesticides and other agrochemicals, leveraging its reactivity to form necessary chemical linkages for effective pest control agents.
Used in Organic Synthesis:
4,5-dibromobenzene-1,2-dicarbonitrile is employed as a reactive building block in organic synthesis, particularly for the formation of carbon-carbon bonds, which is crucial in constructing the frameworks of diverse organic molecules for various applications.

Upstream product

• 91-15-6 phthalonitrile 
• 557-21-1 zinc(II) cyanide 
• 529502-50-9 1,2-dibromo-4,5-diiodobenzene 

Downstream Products

• 304019-13-4 1,2-di(2-thienyl)-4,5-dicyanobenzene 
• 532435-82-8 5,6-dibromo-1,3-diiminoisoindoline 
• 247045-08-5 4,5-bis(tert-butyldimethylsilylethynyl)phthalonitrile 
• 712-74-3 1,2,4,5-tetracyanobenzene 

Relevant academic research and scientific papers

Novel octabromo-substituted lanthanide(III) phthalocyanines – Prospective compounds for nonlinear optics

Novel octabromo-substituted lanthanide(III) phthalocyanines were obtained via template method starting from corresponding 4,5-dibromophthalonitrile and identified by high-resolution mass-spectrometry, 1H nuclear magnetic resonanse and infra red spectroscopy. To achieve an initial 4,5-dibromophthalonitrile the reaction conditions of Pd(0) catalyzed cyanation were optimized. The peripheral bromine atoms impact on the optical properties of phthalocyanine complexes. The bathochromic shift of the main absorption band (Q band) was observed going from unsubstituted to octachloro- and then to octabromo-substituted phthalocyanines. All complexes demonstrated nonlinear optical responses in the DMF solution. Increasing the intensity of laser radiation leads to a nonlinear decrease in transmittance and further restoration of optical properties when switching back to linear mode. Nonlinear optical responses depend on the central ion nature. Europium phthalocyanine showed the enhanced nonlinear absorption coefficient compared to lutetium and terbium complexes. This was caused by an enhanced population of excited state and faster excitement for complexes with large central ions. The impact of peripheral bromine groups into nonlinear optical properties was determined through the comparison with unsubstituted analogues.

A novel modular approach to triazole-functionalized phthalocyanines using click chemistry

(Chemical Equation Presented) A novel, elegant, and significantly improved protocol for the synthesis of a protected octaacetylene phthalocyanine is described. Inexpensive, mild, and environmentally benign iodination of 1,2-dibromobenzene and subsequent optimized chemoselective palladium-catalyzed cyanation are employed to effectively build up the key intermediate 4,5-dibromophthalonitrile in two steps. Introduction of the tert- butyldimethylsilyl-protected acetylene moieties via a Sonogashira cross-coupling provides the desired phthalonitrile precursor that, after cyclization, yielded the protected octaacetylene phthalocyanine. Subsequently, in situ deprotection and "clicking" are employed as a highly efficient and quantitative route to a novel class of octatriazole-functionalized phthalocyanines. The ability of such triazole-derived phthalocyanines to form well-defined supramolecular structures upon doping with zinc(II) triflate is demonstrated.

Vibrational spectra of halophthalonitriles

The fundamental vibrational modes of a series of six halophthalonitriles have been studied using Raman and infrared spectroscopy. The vibrational assignment of experimental wave numbers obtained from solid samples was aided using quantum chemical computations. Semi-empirical methods and the local SVWN functional were used to obtain vibrational wave numbers and atomic displacement representations of the fundamental molecular vibrations. The study of a series of molecules with similar structure permits the identification of characteristic wave numbers and the effect of the halosubstitution in the molecular structure.