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

Name: 2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
Brand: ChemScene
Availability: InStock
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CAS No. 408492-27-3
Cat. No. CS-W010088
Purity≥97%
MDL No.MFCD09746195

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|CS-W010088

Structure of 408492-27-3

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General Information

CAS No. 408492-27-3
Cat. No. CS-W010088
Purity ≥97%
MDL No. MFCD09746195
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₄BCl₂NO₂
Molecular Weight 273.95
Synonym(s) 2,6-Dichloropyridine-4-boronicacidpinacolester
SMILES CC1(C)C(C)(C)OB(C2=CC(Cl)=NC(Cl)=C2)O1

Description

This boronate-functionalized pyridine integrates readily into Suzuki-Miyaura coupling reactions under standard conditions. The 2,6-dichloro substitution pattern enables selective functionalization, while the tetramethyl-1,3,2-dioxaborolane moiety provides enhanced stability and reactivity.

Application

2,6-Dichloro-4-(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 pyridine core provides orthogonal reactivity, while the 2,6-dichloro substitution pattern enables sequential functionalization. The pinacol boronate ester offers excellent bench stability, minimal hydrolysis, and compatibility with diverse reaction conditions, facilitating efficient construction of biaryl and heteroaryl scaffolds in medicinal chemistry and materials science workflows.

Synthesis

Route1
- In-stock
  
  2402-78-0
- 25015-63-8
- ~%
- In-stock
  
  408492-27-3
References
- Board of Trustees of Michigan State University Patent: US2004/30197 A1, 2004 ; Location in patent: Page 14; 17 ;
Route2
- In-stock
  
  2402-78-0
- In-stock
  
  73183-34-3
- ~97%
- In-stock
  
  408492-27-3
References
- Harrisson, Peter; Morris, James; Marder, Todd B.; Steel, Patrick G. Organic Letters, 2009 , vol. 11, # 16 p. 3586 - 3589

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 2.6876
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

Key Words

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

CAS No. 408492-27-3

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