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Merck
CN

473294

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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About This Item

Empirical Formula (Hill Notation):
C12H24B2O4
CAS Number:
73183-34-3
Molecular Weight:
253.94
NACRES:
NA.22
PubChem Substance ID:
24870893
UNSPSC Code:
12352103
MDL number:
MFCD00799570
Assay:
99%
Form:
powder (or crystals)

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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

SMILES string

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

InChI key

IPWKHHSGDUIRAH-UHFFFAOYSA-N

assay

99%

form

powder (or crystals)

mp

137-140 °C (lit.)

Related Categories

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.

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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Certificates of Analysis (COA)

Lot/Batch Number
WXBF7499V
WXBF6647V
WXBF5505V
WXBF2648V
WXBF4376V

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Synlett, 15, 2442-2443 (2003)
Ronald L Reyes et al.
Science (New York, N.Y.), 369(6506), 970-974 (2020-08-21)
Site selectivity and stereocontrol remain major challenges in C-H bond functionalization chemistry, especially in linear aliphatic saturated hydrocarbon scaffolds. We report the highly enantioselective and site-selective catalytic borylation of remote C(sp3)-H bonds γ to the carbonyl group in aliphatic secondary
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)
Bis (pinacolato) diboron
Ishiyama T, et al.
Organic Syntheses, 77(2), 176-185 (2000)
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)
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