Merck
CN
All Photos(6)

Documents

473294

Sigma-Aldrich

Bis(pinacolato)diboron

99%

Sign Into View Organizational & Contract Pricing
All Photos(6)
Synonym(s):
4,4,4′,4′,5,5,5′,5′-Octamethyl-2,2′-bi-1,3,2-dioxaborolane
Empirical Formula (Hill Notation):
C12H24B2O4
CAS Number:
73183-34-3
Molecular Weight:
253.94
MDL number:
MFCD00799570
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

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.

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?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

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)
Synlett, 15, 2442-2443 (2003)
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
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
View All Related Papers

Articles

Ir(I)-Catalyzed C–H Borylation

Arylboronic acids and esters are invaluable tools for the chemical community. These powerful reagents are used for a variety of transformations, most notably the Suzuki-Miyaura cross-coupling reaction.

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