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459496

Sigma-Aldrich

9-Borabicyclo[3.3.1]nonane solution

0.4 M in hexanes

Sinonimo/i:

9-BBN

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About This Item

Formula empirica (notazione di Hill):
C8H15B
Numero CAS:
280-64-8
Peso molecolare:
122.02
Beilstein:
605509
Numero MDL:
MFCD00074742
Codice UNSPSC:
12352005
ID PubChem:
24869563
NACRES:
NA.22

Impiego in reazioni chimiche

reagent type: reductant

Concentrazione

0.4 M in hexanes

P. eboll.

68-70 °C

Densità

0.691 g/mL at 25 °C

Stringa SMILE

B1C2CCCC1CCC2

InChI

1S/C8H15B/c1-3-7-5-2-6-8(4-1)9-7/h7-9H,1-6H2/t7-,8+
FEJUGLKDZJDVFY-OCAPTIKFSA-N

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Categorie correlate

Applicazioni

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

Avvertenze

Danger

Classi di pericolo

Aquatic Chronic 2 - Asp. Tox. 1 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 Inhalation - STOT SE 3 - Water-react 1

Organi bersaglio

Central nervous system, Nervous system

Codice della classe di stoccaggio

4.3 - Hazardous materials which set free flammable gases upon contact with water

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificati d'analisi (COA)

Lot/Batch Number
SHBH9641
SHBD9122V
SHBB2999V
SHBB2999
04509MH

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Sigma-Aldrich

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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
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
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
Rajesh Sardar et al.
Journal of the American Chemical Society, 133(21), 8179-8190 (2011-05-10)
We report a spectroscopic and microscopic investigation of the synthesis of gold nanoparticles (AuNPs) with average sizes of less than 5 nm. The slow reduction and AuNP formation processes that occur by using 9-borabicyclo[3.3.1]nonane (9-BBN) as a reducing agent enabled

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