9-BBN

[9-Borabicyclo[3.3.1]nonane]

General Information:

Structure:

CAS Number: 280-64-8

Molecular Weight: 122.02 g/mol

Appearance: Colorless solid

Melting Point: 153-155

Similar to other dialkylboranes, 9-BBN exists as a dimer. What separates 9-BBN from other dialkylboranes is that it does not need to be freshly prepared prior to use, but rather exists as a stable commercially available crystalline solid.

9-BBN is typically used in organic chemistry for hydroboration-oxidation reactions. 9-BBN is a very useful reagent due to its ability to achieve high regioselectivity in reactions based on steric and electronic factors.

Common Uses:

Reagent in the conversion of alkenes to alcohols via hydroboration-oxidation reactions

Procedure excerpt:

To a solution of the SM (500 mg, 1.82 mmol) in THF (5 mL) was added 9-BBN (0.5 M in THF, 7.30 mL, 3.65 mmol) at RT. The mixture was stirred at RT . . .

[full procedure]

References:

1) Patent Reference: WO2016011930, page 141, (15.7 MB)

2) Wikipedia: 9-Borabicyclo[3.3.1]nonane (link)

3) www.sigmaaldrich.com: 9-Borabicyclo[3.3.1]nonane solution (link)

4) Coates, R. M.; Denmark, S. E.; Handbook of Reagents for Organic Synthesis, Reagents, Auxiliaries, and Catalysts for C-C Bond Formation

5) www.alfa.com: H52287 9-BBN monomer, 97%, 0.5M in THF (link)