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

Name: 4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
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CAS No. 1171891-31-8
Cat. No. CS-W000860
Purity≥97%
MDL No.MFCD12923382

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4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|CS-W000860

Structure of 1171891-31-8

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General Information

CAS No. 1171891-31-8
Cat. No. CS-W000860
Purity ≥97%
MDL No. MFCD12923382
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₈BNO₂
Molecular Weight 219.09
Synonym(s) 4-methylpyridin-3-ylboronic acid pinacol ester
SMILES CC1(C)OB(OC1(C)C)c1cnccc1C

Description

4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine features a boronate ester group enabling efficient Suzuki-Miyaura coupling under mild conditions. The pyridine core provides a robust scaffold for C–C bond formation, while the methyl substituent enhances electronic modulation and solubility. This bench-stable reagent streamlines access to functionalized heteroaryl architectures in medicinal chemistry and materials science.

Application

4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine serves as a robust boronate building block for Suzuki-Miyaura cross-coupling reactions. The pyridine core enables efficient functionalization in medicinal chemistry and materials science, while the pinacol boronate group offers excellent bench stability, ease of handling, and compatibility with diverse reaction conditions. It facilitates the construction of biaryl and heteroaryl scaffolds with high regioselectivity and reproducibility.

Synthesis

Route1
- In-stock
  
  73183-34-3
- In-stock
  
  3430-22-6
- ~%
- In-stock
  
  1171891-31-8
References
- Wang, Lianhui; Cui, Xiuling; Li, Jingya; Wu, Yusheng; Zhu, Zhiwu; Wu, Yangjie European Journal of Organic Chemistry, 2012 , # 3 p. 595 - 603
Route2
- 108-89-4
- In-stock
  
  73183-34-3
- ~9%
- In-stock
  
  1171891-31-8
References
- Larsen, Matthew A.; Hartwig, John F. Journal of the American Chemical Society, 2014 , vol. 136, # 11 p. 4287 - 4299

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 31.35
LogP 1.68922
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

Key Words

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

CAS No. 1171891-31-8

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