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:
Molecular Weight:
122.02
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
605509
form
liquid
Quality Segment
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:
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.
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
Storage Class
4.3 - Hazardous materials which set free flammable gases upon contact with water
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 Dam. 1 - Flam. Liq. 2 - STOT SE 3 - Water-react. 1
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