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473294

Bis(pinacolato)diboron

Name: Bis(pinacolato)diboron
Brand: ALDRICH

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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Properties

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

Description

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.

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.

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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Articles

Rapid Arylboronic Esters Synthesis by Ir(I)-Catalysis

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Global Trade Item Number

SKU	GTIN
473294-5G	04061832360843
473294-100G	04061832360836
473294-1G	04061826672242
473294-25G	04061835555192
473294-500G	04061833547793
473294-500MG	04061833258767