9-Borabicyclo[3.3.1]nonane solution

Name: 9-Borabicyclo[3.3.1]nonane solution
Brand: ALDRICH

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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Properties

form

liquid

Quality Segment

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

Description

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