794287

Bis[(pinacolato)boryl]methane

• 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
• 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

Properties

• 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

Description

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

Safety Information

• 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
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3