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655856 Sigma-Aldrich

4,4,5,5-Tetramethyl-1,3,2-dioxaborolane

97%

Synonym: HBpin, Pinacolborane

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Properties

Related Categories Boronic Acids and Derivatives, Borylation Reagents, Chemical Synthesis, Organometallic Reagents
InChI Key   UCFSYHMCKWNKAH-UHFFFAOYSA-N
assay   97%
refractive index   n20/D 1.396 (lit.)
bp   42-43 °C/50 mmHg(lit.)
density   0.882 g/mL at 25 °C (lit.)
storage temp.   2-8°C

Description

Application

4,4,5,5-Tetramethyl-1,3,2-dioxaborolane may be used for:
• Borylation at the benzylic C-H bond of alkylbenzenes in the presence of a palladium catalyst to form pinacol benzyl boronate.
• Hydroboration of alkyl or aryl alkynes and alkenes in the presence of transition metal catalysts.
• Coupling with aryl iodides in the presence of a copper catalyst to form aryl boronates.
• Asymmetric hydroboration of 1,3-enynes to form chiral allenyl boronates.

Packaging

25, 100, 500 g in Sure/Seal™

5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS02  GHS02
Signal word 
Danger
Hazard statements 
RIDADR 
UN3398 - DOT UN3399 class 4.3 - PG 2 - Organometallic substance, liquid, water-reactive, HI: all (not BR)
WGK Germany 
3
Flash Point(F) 
41 °F
Flash Point(C) 
5 °C

Documents

Certificate of Analysis

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Certificate of Origin

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Protocols & Articles

Articles

Ir(I)-Catalyzed C–H Borylation

Arylboronic acids and esters are invaluable tools for the chemical community. These powerful reagents are used for a variety of transformations, most notably the Suzuki-Miyaura cross-coupling reactio...
Josephine Nakhla
Chemfiles Volume 11 Article 1
Keywords: Catalysis, Coupling reactions, Cross couplings, Infrared spectroscopy

Peer-Reviewed Papers
15

References

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