Skip to Content
Merck
All Photos(2)

Key Documents

794287

Sigma-Aldrich

Bis[(pinacolato)boryl]methane

greener alternative

Synonym(s):

2,2′-Methylenebis[4,4,5,5-tetramethyl-1,3,2-dioxaborolane], Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methane

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C13H26B2O4
CAS Number:
Molecular Weight:
267.97
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.22

form

solid

Quality Level

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

48 °C

greener alternative category

storage temp.

2-8°C

SMILES string

CC(C(C)(C)O1)(C)OB1CB2OC(C)(C)C(C)(C)O2

InChI

1S/C13H26B2O4/c1-10(2)11(3,4)17-14(16-10)9-15-18-12(5,6)13(7,8)19-15/h9H2,1-8H3

InChI key

MQYZGGWWHUGYDR-UHFFFAOYSA-N

General description

Bis[(pinacolato)boryl]methane is an aryl boronate ester.
We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

Application

Bis-boronate has been reported by Morken and coworkers to be a key building block in the synthesis of enantioenriched secondary boronate esters, which undergo facile Suzuki-Miyaura coupling with minimal erosion of enantiopurity.
Bis[(pinacolato)boryl]methane may be used in the preparation of trans-vinyl boronate esters, via the Boron-Wittig reaction.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3


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

John R Coombs et al.
Organic letters, 17(7), 1708-1711 (2015-03-24)
A highly stereoselective boron-Wittig reaction between stable and readily accessible 1,1-bis(pinacolboronates) and aldehydes furnishes a variety of synthetically useful di- and trisubstituted vinyl boronate esters.
A Catalytic Enantiotopic-Group-Selective Suzuki Reaction for the Construction of Chiral Organoboronates
Sun C, et al.
Journal of the American Chemical Society, 136, 6534-6537 (2014)

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