CAS 100-48-1: 4-Cyanopyridine

4-Cyanopyridine

4-Cyanopyridine is used as an intermediate in organic synthesis and pharmaceutical substances like isonicotinylhydrazide, which is used in the treatment of tuberculosis. It is used as a precursor for the preparation of isonicotinic acid and 4-diemthylaminopyridine (DMAP). It is involved in the synthesis of 6-methyl-2-pyridin-4-yl-pyrimidin-4-ylamine by reacting with acetonitrile. This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

This Thermo Scientific Chemicals brand product was originally part of the Acros Organics product portfolio. Some documentation and label information may refer to the legacy brand. The original Acros Organics product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

4-Cyanopyridine is an organic compound with the chemical formula (CN)N. It is a white solid that is soluble in water and polar solvents. When exposed to hydrochloric acid, 4-cyanopyridine undergoes a reaction that converts it to picolinic acid. This reaction proceeds through a mechanism in which the nucleophilic hydroxyl group of 4-cyanopyridine attacks the protonated nitrogen atom of hydrochloric acid. The resulting intermediate then loses a proton and becomes picolinic acid. Kinetic data on this reaction has been obtained from UV-vis spectroscopy, X-ray diffraction, and mass spectrometry experiments. The crystal structures of the bound form of 4-cyanopyridine and its quinoline derivatives have also been determined by x-ray crystallography.

Applications 4-Cyanopyridine is a reagent for the synthesis of 1-tolyl-5-benzylthiotetrazole and 2-hexylthio-4-pyridinecarbonitrile, an antituberculotics. Preparation of the antihypertensive agent Pinacidil using the chemoselective and green oxidative rearrangement of an amidine and addition of an amine to a guanidine as the key step. Structure-based discovery of human L-xylulose reductase inhibitors from database screening and molecular docking. Human L-xylulose reductase (XR) is an enzyme of the glucuronic acid/uronate cycle of glucose metabolism with the possible target for treatment of the long-term complications of diabetes. References Waisser, K., et al.: Folia Pharmaceutica Universitatis Carolinae, 18, 31 (1995); Carbone, V., et al.: Bioorg. Med. Chem., 13, 301 (2004); Baeten, M., et al.: Adv. Synth. Catal., 358, 826 (2016)