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Sigma-Aldrich

Bis(pinacolato)diboron

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

99%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C12H24B2O4
CAS Number:
73183-34-3
Molecular Weight:
253.94
MDL number:
MFCD00799570
UNSPSC Code:
12352103
PubChem Substance ID:
24870893
NACRES:
NA.22
Assay:
99%
form:
powder (or crystals)
Pricing and availability is not currently available.

Assay

99%

form

powder (or crystals)

mp

137-140 °C (lit.)

SMILES string

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

InChI key

IPWKHHSGDUIRAH-UHFFFAOYSA-N

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General description

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]

Application

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]

related product

Product No.
Description
Pricing

907847

HB(trip)2, ≥95%

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF2648V
WXBF3831V
WXBF4376V
WXBF1911V
WXBF0019V

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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)
Synthesis, 2573-2573 (2006)
Takahiro Muraoka et al.
Nature communications, 11(1), 2924-2924 (2020-06-12)
Biological membranes play pivotal roles in the cellular activities. Transmembrane proteins are the central molecules that conduct membrane-mediated biochemical functions such as signal transduction and substance transportation. Not only the molecular functions but also the supramolecular properties of the transmembrane
Synlett, 15, 2442-2443 (2003)
Ignacio A Jessop et al.
Polymers, 13(3) (2021-01-31)
In the search for new materials to fight against antibiotic-resistant bacteria, a hybrid composite from metallic copper nanoparticles (CuNPs) and a novel cationic π-conjugated polyelectrolyte (CPE) were designed, synthesized, and characterized. The CuNPs were prepared by chemical reduction in the
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Articles

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.

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.

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.

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.

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Questions

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  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/449/386/product-dating-information-mk.pdf

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  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

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Reviews

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  1. los angeles
    • Review 1
    • Votes 20
    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 MilliporeSigma:

      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.

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