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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
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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

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

Selective hydroboration reduction reagent.
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

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

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Danger

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

Hazard Classifications

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

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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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

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)
Chemistry Letters (Jpn), 33, 396-397 (2004)
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Global Trade Item Number

SKUGTIN
151076-18L-KL04061838125095
151076-100ML04061838739001
151076-4X25ML04061838739018
151076-PZ04061823818278
151076-800ML04061838739025
151076-8L04061838125101