151076

9-Borabicyclo[3.3.1]nonane solution

0.5 M in THF

• Synonym(s): 9-BBN
• 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

Properties

• 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

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

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.

View returnable container options.

Legal Information

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

Safety Information

• Pictograms: GHS02,GHS08,GHS07
• Signal Word: Danger
• Hazard Statements: H225,H260,H302,H319,H335,H336,H351
• Precautionary Statements: P202 - P210 - P231 + P232 - P301 + P312 - P305 + P351 + P338 - P308 + P313
• 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