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

Name: 2,6-Bis(benzyloxy)-3-bromopyridine
Brand: ChemScene
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CAS No. 16727-47-2
Cat. No. CS-0156153
Purity≥97%
MDL No.MFCD18434484

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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2,6-Bis(benzyloxy)-3-bromopyridine|CS-0156153

Structure of 16727-47-2

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General Information

CAS No. 16727-47-2
Cat. No. CS-0156153
Purity ≥97%
MDL No. MFCD18434484
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₉H₁₆BrNO₂
Molecular Weight 370.24
Synonym(s) 3-bromo-2,6-bis(phenylmethoxy)pyridine
SMILES C1=CC=C(C=C1)COC2=NC(=C(C=C2)Br)OCC3=CC=CC=C3

Description

2,6-Bis(benzyloxy)-3-bromopyridine features a pyridine core functionalized with two benzyloxy groups at the 2 and 6 positions and a bromine atom at the 3 position. This configuration enables selective coupling reactions in late-stage diversification of heterocyclic scaffolds. The benzyl ethers provide stability and solubility, while the electrophilic bromine facilitates cross-coupling transformations under mild conditions.

Application

2,6-Bis(benzyloxy)-3-bromopyridine serves as a versatile building block for the synthesis of substituted pyridine scaffolds in medicinal chemistry and materials science. The benzyloxy groups provide orthogonal protection for phenolic functionalities, while the bromine at C3 enables palladium-catalyzed cross-coupling reactions. Its bench-stable nature and compatibility with standard reaction conditions facilitate efficient downstream transformations in complex molecule assembly.

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 : P233-P260-P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P340-P362-P403-P405-P501

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Computational Chemistry Data

TPSA 31.35
LogP 5.0021
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 6

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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

CAS No. 16727-47-2

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