3-(Methylsulfonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Name: 3-(Methylsulfonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
Brand: ChemScene
Availability: InStock
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CAS No. 1206641-26-0
Cat. No. CS-0046206
Purity≥97%
MDL No.MFCD12198145

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3-(Methylsulfonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|CS-0046206

Structure of 1206641-26-0

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General Information

CAS No. 1206641-26-0
Cat. No. CS-0046206
Purity ≥97%
MDL No. MFCD12198145
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₈BNO₄S
Molecular Weight None
Synonym(s) None
SMILES CC1(C)C(C)(C)OB(C2=CN=CC(S(=O)(C)=O)=C2)O1

Description

This boronate ester features a methylsulfonyl group at the 3-position and a tetramethylboronate handle at the 5-position of a pyridine core. The electron-deficient pyridine ring enhances reactivity in cross-coupling, while the sterically protected boronate moiety ensures stability under standard conditions. This compound integrates readily into Suzuki-Miyaura reactions for constructing complex heteroaromatic scaffolds with high functional group tolerance.

Application

3-(Methylsulfonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The methylsulfonyl group enhances solubility and provides a stable, electron-withdrawing substituent compatible with diverse reaction conditions. The pinacol boronate moiety enables high functional group tolerance, excellent shelf stability, and facile purification, making it ideal for constructing complex pyridine-based scaffolds in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  445491-71-4
- In-stock
  
  73183-34-3
- ~76%
- In-stock
  
  1206641-26-0
References
- MERCK SERONO S.A.; SWINNEN, Dominique; JORAND-LEBRUN, Catherine; GRIPPI-VALLOTTON, Tania; GERBER, Patrick; GONZALEZ, Jerome; SHAW, Jeffrey; JEYAPRAKASHNARAYANAN, Seenisamy Patent: WO2010/100144 A1, 2010 ; Location in patent: Page/Page column 136 ; WO 2010/100144 A1

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS06
Signal Word : Danger	UN#: 2811
Class : 6.1	Packing Group : Ⅲ
Hazard Statements : H301
Precautionary Statements : P264-P270-P330-P405-P501

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Computational Chemistry Data

TPSA 65.49
LogP 0.7843
H_Acceptors 5
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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3-(Methylsulfonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

CAS No. 1206641-26-0

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