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151076

Sigma-Aldrich

9-Borabicyclo[3.3.1]nonane solution

0.5 M in THF

Synonym(s):

9-BBN

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About This Item

Empirical Formula (Hill Notation):
C8H15B
CAS Number:
280-64-8
Molecular Weight:
122.02
Beilstein:
605509
MDL number:
MFCD00074742
UNSPSC Code:
12352005
PubChem Substance ID:
24849089
NACRES:
NA.22

form

liquid

Quality Level

100

reaction suitability

reagent type: reductant

concentration

0.5 M in THF

density

0.894 g/mL at 25 °C

SMILES string

B1C2CCCC1CCC2

InChI

1S/C8H15B/c1-3-7-5-2-6-8(4-1)9-7/h7-9H,1-6H2/t7-,8+

InChI key

FEJUGLKDZJDVFY-OCAPTIKFSA-N

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General description

9-Borabicyclo[3.3.1]nonane is an organic compound, which is generally used as a hydroborating agent. It is thermally stable, less sensitive to oxygen and water when compared to other dialkyl boranes. It is commonly used to prepare aldehydes from alkynes.

Application

Protecting group for alkenes†

Reactant for:
  • Linear SPPS synthesis of ubiquitin derivatives
  • Copper-catalyzed cross-coupling reactions of organoboron compounds with primary alkyl halides and pseudohalides
  • Intramolecular insertion of alkenes into palladium-nitrogen bonds
  • Preparation of (phosphonoacetyl)ornithine to study effect on arginine biosynthetic genes in yeast
  • Hetero-Diels-Alder reaction for synthesis of spirocyclic alkaloids
Differentiation of symmetrical diols by reduction of the corresponding cyclic acetals with 9-BBN.
Selective hydroboration reduction reagent.

Packaging

The 25 mL Sure/Seal™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.
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Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3 - Water-react 1

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

4.3 - Hazardous materials which set free flammable gases upon contact with water

WGK

WGK 3

Flash Point(F)

1.0 °F - closed cup

Flash Point(C)

-17.2 °C - closed cup

Certificates of Analysis (COA)

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Preparation and properties
Hydroboration and Organic Synthesis: 9-Borabicyclo [3.3.1] nonane (9-BBN) (2007)
Zhishan Bo et al.
Organic letters, 6(5), 667-669 (2004-02-28)
Several useful aryl/alkyl building blocks for dendrimer and hyperbranched polymer synthesis were prepared by Suzuki-Miyaura cross-coupling reactions and iododesilylation reactions. The iododesilylations were carried out with iodine monochloride (ICl) in methylene chloride and diethyl ether (10:1). This solvent combination lowered
9-Borabicyclo [3.3. 1] nonane as a convenient selective hydroborating agent
Knights EF and Brown HC
Journal of the American Chemical Society, 90(19), 5281-5283 (1968)
Chemistry Letters (Jpn), 33, 396-397 (2004)
Jefferson D Revell et al.
Organic letters, 7(5), 831-833 (2005-02-25)
1,5-Cyclooctadiene was deprotonated under LICKOR conditions and reacted with Merrifield resin to afford an immobilized cyclooctadiene in high yield. This polymer is effective as a halogen scavenger, while hydroboration leads to a supported 9-BBN analogue. The latter exhibits similar regioselectivity
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Articles

Syntheses of Functionalized Alkenes, Arenes, and Cycloalkenes via a Hydroboration-Coupling Sequence

Tandem hydroboration Suzuki Coupling both intermolecular and intramolecular gave diverse alkyl substituted products dppf

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