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9-BBN dimer acts as a hydroboration reagent in organic chemistry. It is used in Suzuki reactions and involved in the anti-Markovnikov hydration of alkenes and alkynes. It is employed as a reactant for Diels-Alder reaction. In addition to this, it is used as a precursor to boracycles and also selectively reduce conjugated enones to allylic alcohol.
Selective hydroborating agent. For use in hydroboration of terminal alkynes in the synthesis of long-chain alcohols, see: Tetrahedron, 48, 9187 (1992).
For a review of the chemistry of 9-BBN, see: Pure Appl. Chem., 63, 387 (1991); brief reviews of its uses in organic synthesis: J. Prakt. Chem./ Chem. Ztg., 338, 386 (1996); Synlett, 159 (2000).
Braunschweig, H.; Horl, C. Unexpected cluster formation upon hydroboration of a neutral diborene with 9-BBN. Chem. Commun. 2014, 50 (75), 10983-10985.
Farrell, J. M.; Posaratnanathan, R. T.; Stephan, D. W. A family of N-heterocyclic carbene-stabilized borenium ions for metal-free imine hydrogenation catalysis. Chem. Sci. 2015, 6, 2010-2015.
Hazard Statements: H228-H250-H252-H260
Flammable solid. Catches fire spontaneously if exposed to air. Self-heating in large quantities; may catch fire. In contact with water releases flammable gases which may ignite spontaneously.
Precautionary Statements: P223-P210-P222-P231+P232-P422a-P501a
Keep away from any possible contact with water, because of violent reaction and possible flash fire. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not allow contact with air. Handle under inert gas. Protect from moisture. Store contents under inert gas. Dispose of contents/container in accordance with local/regional/national/international regulations.