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Employed in organic synthesis. Addition of catecholborane to vinylarenes in the presence of Wilkinson's catalyst, gives Markovnikov hydroboration products exclusively, whereas the corresponding reaction with a-substituted vinylarenesgivesgood yields of vinylboronate. Hydroboration with catecholborane, followed by treatment with easily available reagents such as alkenyl sulfones or alkynyl phenyl sulfones in the presence of a radical initiator, represents an effective and simple one-pot procedure for direct vinylation, formylation, and cyanation. Catecholborane may be used as a stereoselective reducing agent when converting β-hydroxy ketones to syn 1,3-diols.
Clinton F. Lane,; George W. Kabalka. Catecholborane: A new hydroboration reagent. Tetrahedron. 1976, 32 (9),981-990.
David A. Evans,; Gregory C. Fu. Conjugate reduction of .alpha.,.beta.-unsaturated carbonyl compounds by catecholborane. J. Org. Chem. 1990, 55 (22),5678-5680.
Hazard Statements: H225-H304-H314-H335-H336-H361d-H373
Highly flammable liquid and vapour. May be fatal if swallowed and enters airways. Causes severe skin burns and eye damage. May cause respiratory irritation. May cause drowsiness or dizziness. Suspected of damaging the unborn child. May cause damage to organs through prolonged or repeated exposure.
Precautionary Statements: P201-P202-P210-P233-P235-P240-P241-P242-P243-P260-P264b-P271-P281-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P370+P378q-P501c
Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. 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. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Use personal protective equipment as required. 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. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant