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151076

Sigma-Aldrich

9-Borabicyclo[3.3.1]nonane solution

0.5 M in THF

Sinonimo/i:

9-BBN

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4 X 25 ML
70,00 €
100 ML
99,90 €
800 ML
448,00 €
8 L
2.100,00 €

70,00 €

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Cambia visualizzazione
4 X 25 ML
70,00 €
100 ML
99,90 €
800 ML
448,00 €
8 L
2.100,00 €

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:
24849089
NACRES:
NA.22

70,00 €

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Stato

liquid

Livello qualitativo

100

Impiego in reazioni chimiche

reagent type: reductant

Concentrazione

0.5 M in THF

Densità

0.894 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

Descrizione generale

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.[1][2]

Applicazioni

Differentiation of symmetrical diols by reduction of the corresponding cyclic acetals with 9-BBN.[3]
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
Selective hydroboration reduction reagent.[4][5][6]

Confezionamento

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.

Note legali

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

Avvertenze

Danger

Indicazioni di pericolo

H225,H260,H302,H319,H335,H336,H351

Classi di pericolo

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3 - Water-react 1

Organi bersaglio

Central nervous system, Respiratory system

Rischi supp

EUH019

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)

1.0 °F - closed cup

Punto d’infiammabilità (°C)

-17.2 °C - closed cup

Scegli una delle versioni più recenti:

Certificati d'analisi (COA)

Lot/Batch Number
SHBR9484
SHBQ4924
SHBR0230
STBK7248
STBK7247

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Zhishan Bo et al.
Organic letters, 6(5), 667-669 (2004-02-28)
Several useful aryl/alkyl building blocks for dendrimer and hyperbranched polymer synthesis were prepared by Suzuki-Miyaura cross-coupling reactions and iododesilylation reactions. The iododesilylations were carried out with iodine monochloride (ICl) in methylene chloride and diethyl ether (10:1). This solvent combination lowered
Preparation and properties
Hydroboration and Organic Synthesis: 9-Borabicyclo [3.3.1] nonane (9-BBN) (2007)
Chemistry Letters (Jpn), 33, 396-397 (2004)
9-Borabicyclo [3.3. 1] nonane as a convenient selective hydroborating agent
Knights EF and Brown HC
Journal of the American Chemical Society, 90(19), 5281-5283 (1968)
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
Visualizza tutti i documenti correlati

Articoli

Syntheses of Functionalized Alkenes, Arenes, and Cycloalkenes via a Hydroboration-Coupling Sequence

Tandem hydroboration Suzuki Coupling both intermolecular and intramolecular gave diverse alkyl substituted products dppf

Domande

1–3 di 3 domande  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 risposta

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Utile?

  2. How can I determine the shelf life / expiration / retest date of this product?

    1 risposta

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Utile?

  3. Can you please share the method on how you determine the hydrogen evolution to check the molarity of 9-BBN in THF.

    1 risposta

    1. This product is only MQ100 quality level, which means details on the QC methods cannot be shared. For more information on our M-Clarity program, please see: https://www.sigmaaldrich.com//life-science/quality-and-regulatory-management/m-clarity-program

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