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4-(Bromomethyl)benzonitrile is used in the synthesis of ligands containing a chelating pyrazolyl-pyridine group with a pendant aromatic nitrile. It is also useful in the preparation of 4-[(2H-tetra-zol-2-yl)methyl]benzonitrile by reaction with 2H-tetrazole in the presence of potassium hydroxide.
Alcohols can be protected as their 4-cyanobenzyl ethers, e.g. in the presence of NaH. They can be selectively cleaved by electrolytic reduction: Tetrahrdon Lett., 2643 (1979); Chem. Ber., 114, 946 (1981).
Snelling, R.; Saavedra, J. Z.; Bayrasy, P.; Abdollahian, Y.; Singaram, B. Binary reducing agents containing dichloroindium hydride for the selective, partial, or tandem reductions of bifunctional compounds consisting of halo-nitriles, halo-esters and halo-carboxylic acids. Org. Chem. Front. 2015, 2 (2), 133-140.
Bagala, D. B.; Bhanagea, B. M. Recent Advances in Transition Metal-Catalyzed Hydrogenation of Nitriles. Adv. Synth. Catal. 2015, 357 (5), 883-900.
Hazard Statements: H301-H311-H331-H314-H318-H317
Toxic if swallowed. Toxic in contact with skin. Toxic if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage. May cause an allergic skin reaction.
Precautionary Statements: P260u-P301+P310a-P303+P361+P353-P305+P351+P338-P405-P501a
IF SWALLOWED: 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.