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

Name: 2-Chloro-6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
Brand: ChemScene
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CAS No. 697739-22-3
Cat. No. CS-0128639
Purity≥97%
MDL No.MFCD08063106

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2-Chloro-6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|CS-0128639

Structure of 697739-22-3

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General Information

CAS No. 697739-22-3
Cat. No. CS-0128639
Purity ≥97%
MDL No. MFCD08063106
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₇BClNO₂
Molecular Weight 253.53
Synonym(s) 2-CHLORO-6-METHYLPYRIDINE-4-BORONIC ACID, PINACOL ESTER
SMILES CC1(C)C(C)(C)OB(C2=CC(Cl)=NC(C)=C2)O1

Description

2-Chloro-6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine features a boronate ester group enabling direct Suzuki-Miyaura coupling under mild conditions. The electron-deficient pyridine core enhances reactivity, while the tetramethylcyclopentadienone moiety ensures stability and ease of handling. This reagent streamlines access to functionalized heterocycles in medicinal chemistry and materials science.

Application

2-Chloro-6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine serves as a versatile Suzuki-Miyaura coupling partner, enabling efficient C–C bond formation under mild conditions. The boronate ester group exhibits excellent stability and functional group tolerance, while the chloropyridine moiety facilitates selective cross-coupling with various aryl and heteroaryl halides. This compound functions reliably in the synthesis of biaryl scaffolds common in medicinal chemistry and materials science, offering predictable reactivity and straightforward purification.

Synthesis

Route1
- In-stock
  
  18368-63-3
- In-stock
  
  73183-34-3
- ~84%
- In-stock
  
  697739-22-3
References
- Zeqing, Li; Zhibin, Liang; Yuqiang, Wang; Pei, Yu Research on Chemical Intermediates, 2013 , vol. 39, # 4 p. 1917 - 1926

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 2.34262
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

Key Words

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

CAS No. 697739-22-3

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