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.
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.
Applications
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.
Solubility
Soluble in chloroform and methanol. Insoluble in water.
Notes
Moisture and light sensitive. Store in a cool place. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with oxidizing agents, strong acids and bases.
RUO – Research Use Only
General References:
- 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.