9-Borabicyclo[3.3.1]nonane, CAS No. 280-64-8

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280-64-8

Catalog No. EBD54900

CAS 280-64-8

Name 9-Borabicyclo[3.3.1]nonane

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Basic Information

Synonyms: 9-Borabicyclo[3.3.1]nonane 9-borabicyclo[3.3.1]nonane,9-bbn,inhexanes 9-borabicyclo[3.3.1]nonane,9-bbn,intetrahydrofuran 9-borabicyclo[3.3.1]nonanesolution 9-borabicyclo(3.3.1)nonane,inhexanes 9-borabicyclo(3.3.1)nonane,intetrahydrofuran 9-bbn,0.5msolutionintetrahydrofuran(9-borabicyclo(3.3.1)nonane) 9-borabicyclo(3.3.1)nonane 9-borabicyclo[3.3.1]non-9-yl

Molecular Formula: C8H14B

Molecular Weight: 121.01

MDL Number: MFCD00074742

Categories: Synthetic Chemistry > Organometallic Reagents > Other Organometallic Reagents Synthetic Chemistry > Catalysts and Ligands > Metal-Ligand Complexes

Product Description:

9-Borabicyclo[3.3.1]nonane (9-BBN) is an organoborane compound with the formula C8H15B. It is typically encountered as a dimer, (C8H15B)2, or as a stable complex with tetrahydrofuran (THF) or dimethyl sulfide (DMS). This colorless, air-sensitive liquid is a highly versatile and selective reagent in synthetic organic chemistry. Its primary and most renowned application is in hydroboration reactions. 9-BBN is a sterically hindered borane that exhibits exceptional regioselectivity for the anti-Markovnikov addition of boron and hydrogen across carbon-carbon double bonds, particularly favoring terminal alkenes. The resulting organoborane intermediates are pivotal precursors for a wide range of functional group transformations, including oxidation to primary alcohols, amination, and palladium-catalyzed cross-coupling reactions (e.g., Suzuki-Miyaura coupling). Its selectivity makes it invaluable for the synthesis of complex natural products, pharmaceuticals, and fine chemicals. Beyond its role as a stoichiometric hydroboration reagent, 9-BBN and its derivatives also serve as catalysts or catalyst precursors in various organic transformations, such as hydrosilylation and hydrogenation. Due to its pyrophoric nature and sensitivity to moisture and air, it must be handled under an inert atmosphere (e.g., nitrogen or argon) using standard Schlenk or glovebox techniques.

Physical Properties

Boiling Point: 68-70 °C

Flash Point: 1 °F

Density: 0.691 g/mL at 25 °C

Solubility: reacts

Storage: Flammables area

Safety Information

Packing Level: I

Hazard Category: 4.3(3)

Transport Codes: 3399A

Analytical Data

Appearance: white crystalline powder