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Bromoacetonitrile was used in the synthesis of 1-cyanomethyl-1,1-dimethylhydrazinium bromide. It is used as an alkalyting agent for the nitrogen phosphorus detector.
Carles Miró Sabaté; Henri Delalu; Erwann Jeanneau. Synthesis, characterization, and energetic properties of salts of the 1-cyanomethyl-1,1-dimethylhydrazinium cation. Chemistry An Asian Journal. 2012, 7 (5), 1085-1095 .
Ho-Sang. Shin; Seungki. Kim; Seung-Woon. Myung; Jong-Sei. Park. Iodoacetonitrile and Bromoacetonitrile as Alkylating Reagents for the Nitrogen-Phosphorus Detector. Anal. Chem. 1995, 67 (11), 1853-1859.
Phenols can be protected (K2CO3, acetone) as their cyanomethyl ethers which can be cleaved by hydrogenation of the nitrile: Tetrahedron Lett., 34, 7567 (1993).
The Reformatsky-type reaction with cyclohexanone is more successful in the presence of a Zn/Ag couple than with the conventional Zn-Cu couple: Synth. Commun., 19, 2355 (1989). Good yields of ß-hydroxy nitriles have also been achieved from aldehydes and ketones using Zn and TMS chloride: Tetrahedron Lett., 31, 2205 (1990). The condensation with aldehydes can also be mediated by active Ni: Tetrahedron Lett., 26, 155 (1985). The reaction with aldehydes in the presence of Zn and tri-n-butylphosphine gives ɑß-unsaturated nitriles directly: Synth. Commun., 20, 3277 (1990).
Hazard Statements: H301-H311-H314-H331
Toxic if swallowed. Toxic in contact with skin. Causes severe skin burns and eye damage. Toxic if inhaled.
Precautionary Statements: P260-P264b-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P501c
Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. 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 INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant