Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

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
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C13H26B2O4
CAS Number:
78782-17-9
Molecular Weight:
267.97
MDL number:
MFCD27977747
UNSPSC Code:
12352200
PubChem Substance ID:
329768437
NACRES:
NA.22

form

solid

Quality Level

100

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

48 °C

greener alternative category

Aligned,

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.

Other Notes

A Catalytic Enantiotopic-Group-Selective Suzuki Reaction for the Construction of Chiral Organoboronates

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCQ5620
MKCP9264
MKCP6896
MKCM8853
MKCK7492

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

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

Visit the Document Library

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)
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.

Articles

Carbohydrate-Catalyzed Enantioselective Alkene Diboration

Enantioselective alkene diboration is a valuable strategy for transforming unsaturated hydrocarbons into useful chiral building blocks.

Boronic Acid Esters

The synthesis of biaryl compounds via the Suzuki–Miyaura coupling reaction has become more commonplace now that many arylboronic acids are readily available.

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