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473294

Bis(pinacolato)diboron

99%

Bis(pinacolato)diboron
1 of 1 reviewers took part in a promotion

Synonym(s):

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

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1 g

Available to ship TODAYfromMILWAUKEE

$76.30
5 g

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$155.00
25 g

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$275.00
100 g

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$715.00
500 g

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$1,410.00

About This Item

Empirical Formula (Hill Notation):
C12H24B2O4
CAS Number:
Molecular Weight:
253.94
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:
Assay:
99%
Form:
powder (or crystals)

$76.30


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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

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. It can be synthesized by treating tetrakis(dimethylamino)diboron with pinacol in acidic conditions.

Application

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

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This Item
794287518808473286
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.)


Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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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

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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

1 of 1 reviewers took part in a promotion

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  1. los angeles
    • Review 1
    • Votes 26
    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.