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Acetonitrile is utilized as a polar aprotic solvent in organic synthesis, and in the purification of butadiene. It is used in all the analytical laboratories as a major component of mobile phase in High Performance Liquid Chromatography (HPLC) and in Liquid Chromatography - Mass Spectrometry (LC-MS). It is used for the extraction of fatty acids, spinning fibers and casting and molding of plastic materials. Aqueous two-phase systems based on acetonitrile and carbohydrates play an important character in the extraction and purification of biomolecules called vanillins. It acts as a stabilizer for the chlorinated solvents, and finds use in the production of DNA oligonucleotides.
Polar aprotic solvent for a wide variety of reactions, including nucleophilic substitutions, oxidations, reductions and organometallic reactions. Widely used with crown ethers for the generation of 'naked' anions from their salts; see, e.g. 18-Crown-6, A11249 . Preferred solvent for RuO4 oxidations, due to its coordinating ability; see Ruthenium(III) chloride hydrate, 11043 .
Undergoes the Ritter reaction with alcohols or olefins in the presence of acid to give N-substituted acetamides. For benzylic alcohols, modified conditions employing boron trifluoride etherate give high yields: Synth. Commun., 24, 601 (1994). For an example, see 4-Methylbenzyl alcohol, A15315 .
For use in the mild conversion of amides to nitriles, see Benzamide, A10501 .
Cardoso, G. B.; Mourao, T.; Pereira, F. M.; Freire, M. G.; Fricks, A. T.; Soares, C. M. F.; Lima, A. S. Aqueous two-phase systems based on acetonitrile and carbohydrates and their application to the extraction of vanillin. J. Electroanal. Chem. 2007, 608 (2), 141-147.
Lam, T. W.; Zhang, H.; Siu, S. K. Reductions of Oxygen, Carbon Dioxide, and Acetonitrile by the Magnesium(II)/Magnesium(I) Couple in Aqueous Media: Theoretical Insights from a Nano-Sized Water Droplet. J. Phys. Chem. A 2015, 119 (12), 2780-2792.
Hazard Statements: H225-H302-H312-H332-H319
Highly flammable liquid and vapour. Harmful if swallowed. Harmful in contact with skin. Harmful if inhaled. Causes serious eye irritation.
Precautionary Statements: P210-P261-P280-P303+P361+P353-P305+P351+P338-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Dispose of contents/container in accordance with local/regional/national/international regulations.