Skip to Content
Merck
All Photos(6)

Documents

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

Sign Into View Organizational & Contract Pricing
All Photos(6)

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)

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

Looking for similar products? Visit Product Comparison Guide

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

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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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)
Catalysis of the coupling reaction of aryl chlorides with bis (pinacolato) diboron by tricyclohexylphosphine-cyclopalladated ferrocenylimine complexes
Xu C, et al.
Transition Metal Chemistry, 34(2), 175-179 (2009)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service