Pular para o conteúdo
Merck

473294

Sigma-Aldrich

Bis(pinacolato)diboron

99%

Bis(pinacolato)diboron
1 of 1 reviewers received a sample product or took part in a promotion

Sinônimo(s):

4,4,4′,4′,5,5,5′,5′-Octamethyl-2,2′-bi-1,3,2-dioxaborolane

Slide 1 of 6
Faça loginpara ver os preços organizacionais e de contrato

Selecione um tamanho

Preço e disponibilidade não estão disponíveis no momento.

Sobre este item

Fórmula empírica (Notação de Hill):
C12H24B2O4
Número CAS:
73183-34-3
Peso molecular:
253.94
Número MDL:
MFCD00799570
Código UNSPSC:
12352103
ID de substância PubChem:
24870893
NACRES:
NA.22

Documentos Principais

Visualizar Toda a Documentação

Pular para

Assistência Técnica
Precisa de ajuda? Nossa equipe de cientistas experientes está à sua disposição.
Estamos aqui para ajudar

Ensaio

99%

Formulário

powder (or crystals)

pf

137-140 °C (lit.)

cadeia de caracteres SMILES

CC1(C)OB(OC1(C)C)B2OC(C)(C)C(C)(C)O2

InChI

1S/C12H24B2O4/c1-9(2)10(3,4)16-13(15-9)14-17-11(5,6)12(7,8)18-14/h1-8H3

chave InChI

IPWKHHSGDUIRAH-UHFFFAOYSA-N

Procurando produtos similares? Visita Guia de comparação de produtos

Categorias relacionadas

Comparar Itens Semelhantes

Ver Comparação Total

Mostrar diferenças

1 of 4

Este Item
794287518808473286
Bis(pinacolato)diboron 99%

Sigma-Aldrich

473294

Bis(pinacolato)diboron

Bis[(pinacolato)boryl]methane

Sigma-Aldrich

794287

Bis[(pinacolato)boryl]methane

Bis(neopentyl glycolato)diboron 96%

Sigma-Aldrich

518808

Bis(neopentyl glycolato)diboron

Bis(catecholato)diboron 97%

Sigma-Aldrich

473286

Bis(catecholato)diboron

form

powder (or crystals)

form

solid

form

-

form

-

assay

99%

assay

-

assay

96%

assay

97%

mp

137-140 °C (lit.)

mp

48 °C

mp

180.5-184.5 °C (lit.)

mp

189-196 °C (lit.)

Descrição geral

Bis(pinacolato)diboron or (B2pin2) is the most commonly used diborane reagent in organic synthesis due to its high stability in air and moisture.[1][2][3] It can be synthesized by treating tetrakis(dimethylamino)diboron with pinacol in acidic conditions.[4]

Aplicação

Reagent used for the cis-vicinal diborylation of acetylenes and olefins with Pt catalysis; borylation of aromatics by Pd catalysis.[5]
Substrate used in a new palladium-catalyzed cyclization of 1,6-enynes leading to homoallylic alkylboronates.[6]
Used to construct a tetramethylpyrrolidine nitroxide scaffold for the synthesis of paramagnetic heterocycles by Suzuki coupling.[7]

produto relacionado

Nº do produto
Descrição
Preços

907847

HB(trip)2, ≥95%

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)

Escolha uma das versões mais recentes:

Certificados de análise (COA)

Lot/Batch Number
WXBF7499V
WXBF6647V
WXBF5505V
WXBF2648V
WXBF4376V

Não está vendo a versão correta?

Se precisar de uma versão específica, você pode procurar um certificado específico pelo número do lote ou da remessa.

Pesquise por COA

Já possui este produto?

Encontre a documentação dos produtos que você adquiriu recentemente na biblioteca de documentos.

Visite a Biblioteca de Documentos

Synthesis, 2573-2573 (2006)
Pd-catalyzed borylative cyclization of 1,6-enynes.
Juan Marco-Martínez et al.
Journal of the American Chemical Society, 129(7), 1874-1875 (2007-01-31)
Synlett, 15, 2442-2443 (2003)
Iridium-catalyzed C-H coupling reaction of heteroaromatic compounds with bis (pinacolato) diboron: regioselective synthesis of heteroarylboronates
Takagi J, et al.
Tetrahedron Letters, 43(32), 5649-5651 (2002)
Bis (pinacolato) diboron
Ishiyama T, et al.
Organic Syntheses, 77(2), 176-185 (2000)
Exibir todos os documentos relacionados

Artigos

Rapid Arylboronic Esters Synthesis by Ir(I)-Catalysis

Arylboronic acids and esters, vital tools in chemical transformations, find extensive use, particularly in the Suzuki-Miyaura cross-coupling reaction.

Conteúdo relacionado

1 Review This action will navigate to reviews.

Questions

1–2 of 2 Questions  

  1. 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/418/501/product-dating-information-06-25-mk.pdf

      Helpful?

  2. 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

      Helpful?

1 Review This action will navigate to reviews.
1 of 1 reviewers received a sample product or took part in a promotion
0 out of 1 (0%) reviewers recommend this product

Reviews

Active Filters

  1. los angeles
    • Review 1
    • Votes 23
    1 out of 5 stars.

    Contaminated

    11B NMR showed significant impurities that likely inhibited the desired reactivity (Hartwig borylation), other vendors sell lots that do not have these impurities and perform more consistently

    Helpful?

    1. Response from Merck KGaA:

      Thank you for your review. We are sorry to hear that your experience did not match your product expectations. This product has been tested to meet our 99% Purity (GC) spec. If you are experiencing problems with impurities, call or email us with your Proudct Order and Lot Number for additional technical support. Please visit https://www.sigmaaldrich.com/US/en/support/customer-support to submit a Product Technical Inquiry.

Nossa equipe de cientistas tem experiência em todas as áreas de pesquisa, incluindo Life Sciences, ciência de materiais, síntese química, cromatografia, química analítica e muitas outras.

Entre em contato com a assistência técnica