459496
9-Borabicyclo[3.3.1]nonane solution
0.4 M in hexanes
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
Quality Level
reaction suitability
reagent type: reductant
concentration
0.4 M in hexanes
bp
68-70 °C
density
0.691 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
Application
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
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signalword
Danger
target_organs
Central nervous system, Nervous system
Storage Class
4.3 - Hazardous materials which set free flammable gases upon contact with water
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Classifications
Aquatic Chronic 2 - Asp. Tox. 1 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 Inhalation - STOT SE 3 - Water-react. 1
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Jefferson D Revell et al.
Organic letters, 7(5), 831-833 (2005-02-25)
1,5-Cyclooctadiene was deprotonated under LICKOR conditions and reacted with Merrifield resin to afford an immobilized cyclooctadiene in high yield. This polymer is effective as a halogen scavenger, while hydroboration leads to a supported 9-BBN analogue. The latter exhibits similar regioselectivity
A Ganesan
Mini reviews in medicinal chemistry, 6(1), 3-10 (2006-02-07)
Solid-phase synthesis is a powerful tool for achieving high-throughput chemistry. This review discusses recent diverse examples from my group: the solid-phase synthesis of unsymmetrical guanidines, polymer-supported versions of cyclooctadiene and 9-BBN, a triflate-like linker, the synthesis of tetrahydro-beta-carbolines by the
Yi Luan et al.
Organic letters, 13(9), 2510-2513 (2011-04-09)
Diazo esters, arylboranes, and carbamoyl imines undergo a 3-component Mannich condensation reaction. Catalyzed by Cu(II) salts, the reaction affords the corresponding isocyanate Mannich product: one that can be easily trapped in situ by other nucleophiles. The Mannich condensation corresponds to