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

Name: 3-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
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CAS No. 1171891-42-1
Cat. No. CS-0042059
Purity≥97%
MDL No.MFCD09265531

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3-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|CS-0042059

Structure of 1171891-42-1

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General Information

CAS No. 1171891-42-1
Cat. No. CS-0042059
Purity ≥97%
MDL No. MFCD09265531
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₈BNO₂
Molecular Weight 219.09
Synonym(s) 5-Methylpyridin-3-ylboronic acid pinacol ester
SMILES CC1=CC(=CN=C1)B1OC(C)(C)C(C)(C)O1

Description

3-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine features a boronate ester group conjugated to a pyridine ring with a methyl substituent at the 3-position. This configuration enhances stability and reactivity in Suzuki-Miyaura coupling reactions. The tetramethyl-substituted dioxaborolane moiety ensures excellent shelf life and moisture tolerance. The compound integrates readily into complex molecular architectures under standard conditions.

Application

3-Methyl-5-(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 tetramethylboronate group enables high functional group tolerance and stability under ambient conditions, facilitating efficient C–C bond formation with aryl and heteroaryl halides. Its pyridine core provides a rigid, electron-deficient scaffold suitable for medicinal chemistry applications and transition metal-catalyzed transformations.

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 1.68922
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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3-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

CAS No. 1171891-42-1

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