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Merck
CN

151076

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
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24849089
MDL number:
MFCD00074742
Beilstein/REAXYS Number:
605509

Key Documents

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Product Name

9-Borabicyclo[3.3.1]nonane solution, 0.5 M in THF

InChI

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

SMILES string

B1C2CCCC1CCC2

InChI key

FEJUGLKDZJDVFY-OCAPTIKFSA-N

form

liquid

reaction suitability

reagent type: reductant

concentration

0.5 M in THF

density

0.894 g/mL at 25 °C

Quality Level

100

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Packaging

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

Legal Information

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

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

Differentiation of symmetrical diols by reduction of the corresponding cyclic acetals with 9-BBN.
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
Selective hydroboration reduction reagent.

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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

supp_hazards

EUH019

Storage Class

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
SHBT2690
SDBB4977
SHBR9484
SHBQ4924
SHBR0230

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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
Preparation and properties
Hydroboration and Organic Synthesis: 9-Borabicyclo [3.3.1] nonane (9-BBN) (2007)
Organic Process Research & Development, 10, 1076-1076 (2006)
Chemistry Letters (Jpn), 33, 396-397 (2004)
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)
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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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