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473294

Sigma-Aldrich

Bis(pinacolato)diboron

99%

Synonym(s):

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

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250 MG
MYR 450.00

MYR 450.00


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250 MG
MYR 450.00

About This Item

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

MYR 450.00


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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

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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]

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Product No.
Description
Pricing

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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    Jorge Regueiro et al.
    Rapid communications in mass spectrometry : RCM, 29(16), 1473-1484 (2015-07-28)
    Due to the growing restrictions on the use of bisphenol A (BPA), several other bisphenols are gaining importance as substitutes for BPA in a variety of applications. There is, therefore, a real need for selective and sensitive methods based on

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