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

Name: 5-Fluoro-2-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
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CAS No. 1083168-95-9
Cat. No. CS-0040531
Purity≥96%
MDL No.MFCD08063053

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5-Fluoro-2-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|CS-0040531

Structure of 1083168-95-9

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General Information

CAS No. 1083168-95-9
Cat. No. CS-0040531
Purity ≥96%
MDL No. MFCD08063053
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₇BFNO₃
Molecular Weight 253.08
Synonym(s) 5-FLUORO-2-METHOXYPYRIDINE-3-BORONIC ACID PINACOL ESTER
SMILES CC1(C)C(C)(C)OB(C2=CC(F)=CN=C2OC)O1

Description

This boronate ester features a 5-fluoro-2-methoxy-3-pyridyl scaffold, enabling efficient cross-coupling under standard conditions. The tetramethyl-substituted dioxaborolane group enhances stability and reactivity, facilitating direct incorporation into complex molecular architectures via palladium-catalyzed transformations.

Application

5-Fluoro-2-methoxy-3-(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 enables transition-metal-catalyzed C–C bond formation, while the 5-fluoro and 2-methoxy substituents provide orthogonal reactivity and electronic tuning. The pinacol boronate group offers excellent bench stability, ease of purification, and compatibility with a broad range of coupling partners, facilitating efficient synthesis of substituted heterocycles and complex pharmaceutical scaffolds.

Synthesis

Route1
- In-stock
  
  884494-81-9
- In-stock
  
  73183-34-3
- ~61%
- In-stock
  
  1083168-95-9
References
- VERTEX PHARMACEUTICALS INCORPORATED Patent: WO2008/141119 A2, 2008 ; Location in patent: Page/Page column 105 ; WO 2008/141119 A2

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 40.58
LogP 1.5285
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 2

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

CAS No. 1083168-95-9

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