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655074 Sigma-Aldrich

5-Methylthiophene-2-boronic acid pinacol ester

95%

Synonym: 5-(2-Methylthiophene)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

  • CAS Number 476004-80-5

  • Empirical Formula (Hill Notation) C11H17BO2S

  • Molecular Weight 224.13

  •  MDL number MFCD05664108

  •  PubChem Substance ID 24884082

  •  NACRES NA.22

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Properties

Related Categories Boronate Esters, Boronic Acids and Derivatives, Chemical Synthesis, Heteroaryl Boronate Esters, Organometallic Reagents More...
Quality Level   100
assay   95%
impurities   4-5% pinacol
density   0.937 g/mL at 25 °C (lit.)
SMILES string   Cc1ccc(s1)B2OC(C)(C)C(C)(C)O2
InChI   1S/C11H17BO2S/c1-8-6-7-9(15-8)12-13-10(2,3)11(4,5)14-12/h6-7H,1-5H3
InChI key   LTOLNTYOBPPFLS-UHFFFAOYSA-N

Description

Application

5-Methylthiophene-2-boronic acid pinacol ester can be used as a reactant:
•  In the palladium-catalyzed Suzuki coupling reaction for the preparation of heteroaryl derivatives.
•  To synthesize N-(4-methylpyridin-2-yl)thiophene-2-carboxamide analog as potential inhibitor of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE).
•  To prepare organic recyclable mechanoluminescent luminogen via Wittig and Suzuki reactions.

Packaging

1, 10 g in glass bottle

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 2
Flash Point(F) 
221.0 °F
Flash Point(C) 
105 °C
Protocols & Articles

Articles

Boronic Acid Esters - Chemfiles Volume 4 Article 2

The synthesis of biaryl compounds via the Suzuki–Miyaura coupling reaction has become more commonplace now that many arylboronic acids are readily available. Several years ago, Miyaura et al. demonst...
Chemfiles Volume 4 Article 2
Keywords: Coupling reactions, Suzuki-Miyaura coupling

Peer-Reviewed Papers
15

References

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