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151076 Aldrich

9-Borabicyclo[3.3.1]nonane solution

0.5 M in THF

Synonym: 9-BBN

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Properties

Related Categories 25mL Sure/Seal Reagents, Boranes, Chemical Synthesis, Organometallic Reagents, Reduction,
InChI Key   FEJUGLKDZJDVFY-OCAPTIKFSA-N
concentration   0.5 M in THF
density   0.894 g/mL at 25 °C

Description

Application

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

Selective hydroboration reduction reagent.

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

4×25, 100, 800 mL in Sure/Seal™

8, 18 L in Kilo-Lab™

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

Price and Availability

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Supplemental Hazard Statements 
May form explosive peroxides.
RIDADR 
UN 3399A 4.3(3) / PGI
WGK Germany 
3
Flash Point(F) 
1.4 °F
Flash Point(C) 
-17 °C
Protocols & Articles

Articles

Palladium-catalyzed inter- and intramolecular cross-coupling reactions of B-alkyl-9-borabicyclo[3.3.1]nonane derivatives with 1-halo-1-alkenes or haloarenes. Syntheses of functionalized alkenes, arenes, and cycloalkenes via a hydroboration-coupling sequence

The cross-coupling reaction of B-alkyl-9-borabicyclo[3.3.l]nonanes (B-R-9 BBN), readily obtainable from alkenes by hydroboration, with 1-halo-1-alkenes or haloarenes in the presence of a catalytic am...
Keywords: Catalysis, Chromatography, Column chromatography, Coupling reactions, Cross couplings, Oxidations

Reagents for C–C Bond Formation

Aldrich carries a large variety of electrophiles and nucleophiles that are widely used in C–C bond-forming reactions. This group of products contains many organometallic reagents as well as commonly-...
ChemFiles Volume 1 Article 3
Keywords: Acylations, Alkylations

Peer-Reviewed Papers
15

References

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