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151076

Sigma-Aldrich

9-Borabicyclo[3.3.1]nonane solution

0.5 M in THF

Sinônimo(s):

9-BBN

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About This Item

Fórmula empírica (Notação de Hill):
C8H15B
Número CAS:
280-64-8
Peso molecular:
122.02
Beilstein:
605509
Número MDL:
MFCD00074742
Código UNSPSC:
12352005
ID de substância PubChem:
24849089
NACRES:
NA.22
Preço e disponibilidade não estão disponíveis no momento.

Formulário

liquid

Nível de qualidade

100

adequação da reação

reagent type: reductant

concentração

0.5 M in THF

densidade

0.894 g/mL at 25 °C

cadeia de caracteres SMILES

B1C2CCCC1CCC2

InChI

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

chave InChI

FEJUGLKDZJDVFY-OCAPTIKFSA-N

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Descrição geral

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]

Aplicação

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]

Embalagem

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.

Informações legais

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

Palavra indicadora

Danger

Classificações de perigo

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

Órgãos-alvo

Central nervous system, Respiratory system

Perigos de suplementos

EUH019

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

1.0 °F - closed cup

Ponto de fulgor (°C)

-17.2 °C - closed cup

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Certificados de análise (COA)

Lot/Batch Number
SHBR9484
SHBQ4924
SHBR0230
STBK7247
STBK7248

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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)
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)
Chemtracts, 13, 219-222 (2000)
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Artigos

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

Questions

1–3 of 3 Questions  

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

    1 answer

    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

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

    1 answer

    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

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

    1 answer

    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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