Catalysis and Inorganic Chemistry
Acetonitrile is a common two-carbon building block in organic synthesisof many useful chemicals, including acetophene, thiamine, acetamidine, and α-napthaleneacetic acid. Its reaction with cyanogen chloride affords malononitrile.
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Acetonitrile is the chemical compound with the formula CH3CN. This colourless liquid is the simplest organic nitrile (hydrogen cyanide is a simpler nitrile, but the cyanide anion is not classed as organic). It is produced mainly as a byproduct of acrylonitrile manufacture. It is used as a polar aprotic solvent in organic synthesis and in the purification of butadiene.
In the laboratory, it is used as a medium-polarity solvent that is miscible with water and has a convenient liquid range. With a dipole moment of 3.92 D, acetonitrile dissolves a wide range of ionic and nonpolar compounds (e.g. Wohl-Ziegler reaction) and is useful as a mobile phase in HPLC and LCMS.
Acetonitrile was first prepared in 1847 by the French chemist Jean-Baptiste Dumas.
Cu-catalyzed cyanation of indoles with acetonitrile for the synthesis of 3-cyanoindoles has been developed. The Cu/TEMPO/(Me3Si)2 system has been identified to promote highly efficient and selective C–H cyanation of indoles by use of unactivated acetonitrile as a cyano source via a sequential iodination/cyanation process in one pot. This reaction furnishes 3-cyanoindoles in moderate to good yields and tolerates a series of functional groups. Moreover, low-cost copper catalysts and hazardless acetonitrile as a cyano source feature the practicability of this reaction.