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Bis[(pinacolato)boryl]methane

Name: Bis[(pinacolato)boryl]methane
Brand: ALDRICH

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

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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

Related Categories

Boronic Acids & Derivatives

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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

GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Certificates of Analysis (COA)

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Synthesis of vinyl boronates from aldehydes by a practical boron-Wittig reaction.

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.