2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Name: 2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
Brand: ChemScene
Availability: InStock
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CAS No. 325142-95-8
Cat. No. CS-W006744
Purity≥97%
MDL No.MFCD11617853

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Type	HazMat Fee
Excepted Quantity	$0.00
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2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|CS-W006744

Structure of 325142-95-8

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General Information

CAS No. 325142-95-8
Cat. No. CS-W006744
Purity ≥97%
MDL No. MFCD11617853
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₂₀BNO₂
Molecular Weight 233.12
Synonym(s) 2,6-DIMETHYLPYRIDINE-4-BORONIC ACID, PINACOL ESTER
SMILES CC1(C)C(C)(C)OB(C2=CC(C)=NC(C)=C2)O1

Description

This boronate-functionalized pyridine features a sterically protected tetramethylboronate group, enabling stable coupling under standard Suzuki-Miyaura conditions. The 2,6-dimethyl substitution enhances solubility and minimizes aggregation, while the electron-deficient pyridine ring facilitates efficient cross-coupling with aryl halides.

Application

2,6-Dimethyl-4-(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 sterically protected boronate group exhibits excellent stability under ambient conditions and resists protodeboronation, enabling reliable coupling with aryl and heteroaryl halides. Its pyridine core facilitates downstream functionalization, while the 2,6-dimethyl substitution enhances solubility and minimizes undesired side reactions. This reagent functions effectively in diverse synthetic workflows requiring selective C–C bond formation.

Synthesis

Route1
- 108-48-5
- In-stock
  
  73183-34-3
- ~98%
- In-stock
  
  325142-95-8
References
- Obligacion, Jennifer V.; Semproni, Scott P.; Chirik, Paul J. Journal of the American Chemical Society, 2014 , vol. 136, # 11 p. 4133 - 4136
Route2
- 108-48-5
- 25015-63-8
- ~41%
- In-stock
  
  325142-95-8
References
- Cho; Iverson; Smith III Journal of the American Chemical Society, 2000 , vol. 122, # 51 p. 12868 - 12869

Safety Information

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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 1.99764
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

CAS No. 325142-95-8

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