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3-Bromopyridine undergoes lithiation with LDA at low temperatures in the 4-position: Heterocycles, involved in formation of the Grignard by Mg exchange with i-PrMgCl and in transmetallation of the lithiated derivative with zinc chloride followed by treatment with an electrophile as a route to 4-substituted 3-bromopyridines.
Jennifer A. Love Dr.; John P. Morgan.;Tina M. Trnka.;Robert H. Grubbs Prof. A Practical and Highly Active Ruthenium-Based Catalyst that Effects the Cross Metathesis of Acrylonitrile. Angewandte Chemie International Edition. 2002, 41 (21), 4035-4037.
Wenjie Li.; Dorian P. Nelson.; Mark S. Jensen.; R. Scott Hoerrner.; Dongwei Cai.; Robert D. Larsen.; Paul J. Reider. An Improved Protocol for the Preparation of 3-Pyridyl- and Some Arylboronic Acids. J. Org. Chem. 2002, 57 (16), 5394-5397.
Undergoes lithiation with LDA at low temperatures in the 4-position: Heterocycles, 35, 151 (1993). Formation of the Grignard by Mg exchange with i-PrMgCl: Tetrahdron Lett., 40, 4339 (1999). Transmetallation of the lithiated derivative with ZnCl2 followed by treatment with an electrophile has been described, as a route to 4-substituted 3-bromopyridines: Org. Lett., 3, 835 (2001).
Hazard Statements: H226-H301-H311-H315-H319-H331-H335
Flammable liquid and vapour. Toxic if swallowed. Toxic in contact with skin. Causes skin irritation. Causes serious eye irritation. Toxic if inhaled. May cause respiratory irritation.
Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P261-P264b-P270-P271-P280-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P311-P312-P330-P332+P313-P337+P313-P363-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Avoid breathing 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 SWALLOWED: Immediately call a POISON CENTER or doctor/physician. 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. Call a POISON CENTER or doctor/physician. Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant