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Sigma-Aldrich

Bis[(pinacolato)boryl]methane

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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

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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
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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.
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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

Certificates of Analysis (COA)

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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.

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