Pyridine is a basic heterocyclic organic compound with the chemical formula C5H5N. It is structurally related to benzene, with one methine group (=CH?) replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with a distinctive, unpleasant fish-like smell. Pyridine is colorless, but older or impure samples can appear yellow. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Historically, pyridine was produced from coal tar. Today it is synthesized on the scale of about 20,000 tons per year worldwide.
3-Hydroxypyridine is a pyridine derivative with a hydroxyl group in position 3. It is a light brown to beige powder. The substance is irritating to the eyes, the respiratory system and the skin. 3-Hydroxypyridine is harmful if inhaled, swallowed or absorbed through the skin. Effects of acute 3-hydroxypyridine intoxication include dizziness, headache, lack of coordination, nausea, salivation, and loss of appetite. They may progress into abdominal pain, pulmonary congestion and unconsciousness.
The compound can be prepared by the hydrolysis of pyridine-3-sulfonic acid or the potassium and sodium salts of this sulfonic acid in aqueous solution. The main use of 3-hydroxypyridine is as a precursor to the herbicides paraquat and diquat. The first synthesis step of insecticide chlorpyrifos consists of the chlorination of pyridine. Pyridine is also the starting compound for the preparation of pyrithione-based fungicides. Cetylpyridinium and laurylpyridinium, which can be produced from pyridine with a Zincke reaction, are used as antiseptic in oral and dental care products. Pyridine is easily attacked by alkylating agents to give N-alkylpyridinium salts.
3-Hydroxypyridine is an intermediate in the synthesis of various biologically active substances, such as drugs or herbicides , including 2-chloro-3-hydroxypyridine by reaction of 3-hydroxypyridine with sodium hypochlorite . It is an intermediate compound in the synthesis of herbicides. 2-amino-3-hydroxypyridine , by the Chichibabin reaction of 3-hydroxypyridine with sodium amide. 2-Amino-3-hydroxypyridine is an intermediate in the synthesis of various drugs and also certain azo dyes.
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