2,6-Bis(benzyloxy)-3-iodopyridine

Name: 2,6-Bis(benzyloxy)-3-iodopyridine
Brand: ChemScene
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CAS No. 2259853-06-8
Cat. No. CS-0643735
Molecule weight417.24
Purity≥97%
MDL No.None

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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2,6-Bis(benzyloxy)-3-iodopyridine|CS-0643735

Structure of 2259853-06-8

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General Information

CAS No. 2259853-06-8
Cat. No. CS-0643735
Purity ≥97%
MDL No. None
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₉H₁₆INO₂
Molecular Weight 417.24
Synonym(s) None
SMILES IC1=CC=C(OCC2=CC=CC=C2)N=C1OCC3=CC=CC=C3

Description

2,6-Bis(benzyloxy)-3-iodopyridine features a pyridine core functionalized with two benzyloxy groups at the 2 and 6 positions and an iodine atom at the 3 position. This configuration enables efficient cross-coupling reactions in late-stage diversification, particularly in Suzuki-Miyaura and Negishi protocols. The benzyloxy substituents provide steric protection and enhance solubility, while the iodide serves as a high-reactivity handle for transition-metal-catalyzed transformations. The molecule exhibits excellent bench stability under standard conditions.

Application

2,6-Bis(benzyloxy)-3-iodopyridine serves as a versatile building block for late-stage functionalization in medicinal chemistry and heterocyclic synthesis. The iodine moiety enables palladium-catalyzed cross-coupling reactions with broad functional group tolerance, while the ortho-benzyloxy groups provide steric protection and enhanced solubility. This compound exhibits excellent bench stability and facilitates efficient purification, making it well-suited for iterative synthetic sequences and API intermediate development.

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 4.8442
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 6

Other Classifications

Building Blocks Functional Group Ether

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Drug Discovery Inflammation/Immunology IRAK4

Key Words

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2,6-Bis(benzyloxy)-3-iodopyridine

CAS No. 2259853-06-8

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