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

Name: 2,6-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
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CAS No. 693774-10-6
Cat. No. CS-0036233
Purity≥97%
MDL No.None

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2,6-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|CS-0036233

Structure of 693774-10-6

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General Information

CAS No. 693774-10-6
Cat. No. CS-0036233
Purity ≥97%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₂₀BNO₂
Molecular Weight 233.11
Synonym(s) 3-Hydroxy-2,3-diMethylbutan-2-yl hydrogen (2,6-diMethylpyridin-3-yl)boronate
SMILES CC1=NC(=C(C=C1)B2OC(C)(C)C(C)(C)O2)C

Description

This pyridine boronate features a sterically hindered 2,6-dimethyl substitution pattern that enhances stability and minimizes undesired side reactions. The tetramethylborolane moiety enables efficient coupling under mild conditions, making it ideal for Suzuki-Miyaura cross-coupling applications in complex molecule synthesis.

Application

2,6-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. Its ortho-methyl groups enhance regioselectivity and electronic modulation in heterocyclic coupling, while the sterically protected boronate moiety ensures excellent shelf stability and compatibility with diverse functional groups. Ideal for constructing complex pyridine-based scaffolds in medicinal chemistry and materials science applications.

Synthesis

Route1
- 61676-62-8
- ~99%
- In-stock
  
  693774-10-6
References
- Cowart, Marlon D.; Sun, Minghua; Zhao, Chen; Zheng, Guo Zhu Patent: US2007/66588 A1, 2007 ; Location in patent: Page/Page column 29-30 ; US 20070066588 A1

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 1.99764
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-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

CAS No. 693774-10-6

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