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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-X
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: P210-P222-P223-P231+P232-P235+P410-P240-P241-P280-P335+P334-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not allow contact with air. Keep away from any possible contact with water, because of violent reaction and possible flash fire. Handle under inert gas. Protect from moisture. Keep cool. Protect from sunlight. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Wear protective gloves/protective clothing/eye protection/face protection. Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant