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459496

Sigma-Aldrich

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:
280-64-8
Molecular Weight:
122.02
Beilstein:
605509
MDL number:
MFCD00074742
UNSPSC Code:
12352005
PubChem Substance ID:
24869563
NACRES:
NA.22

Quality Level

100

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

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Related Categories

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

Signal Word

Danger

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

Target Organs

Central nervous system, Nervous system

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 3: Spontaneously combustible substances and water- reactive materials
Materials containing Organometallic compounds
Hazardous rank I
1st spontaneously combustible materials and water reactive materials

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

459496-1L:4548173154442
459496-BULK:
459496-100ML:4548173154435
459496-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
SHBH9641
SHBD9122V
SHBB2999V
SHBB2999
04509MH

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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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