5-Bromo-2-chloro-3-methoxypyridine

Name: 5-Bromo-2-chloro-3-methoxypyridine
Brand: ChemScene
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CAS No. 286947-03-3
Cat. No. CS-W003476
Purity≥98%
MDL No.MFCD08234976

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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5-Bromo-2-chloro-3-methoxypyridine|CS-W003476

Structure of 286947-03-3

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General Information

CAS No. 286947-03-3
Cat. No. CS-W003476
Purity ≥98%
MDL No. MFCD08234976
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₅BrClNO
Molecular Weight 222.47
Synonym(s) 5-Brom-2-chlor-3-methoxypyridin
SMILES COC(C=C(Br)C=N1)=C1Cl

Description

5-Bromo-2-chloro-3-methoxypyridine is a halogenated pyridine derivative featuring complementary reactive sites for cross-coupling and functionalization. The bromo group enables palladium-catalyzed coupling, while the chloro moiety offers orthogonal reactivity under selective conditions. This electron-deficient heterocycle integrates readily into complex scaffolds for medicinal chemistry and materials science applications.

Application

5-Bromo-2-chloro-3-methoxypyridine serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its complementary halogen reactivity. The bromo group facilitates Suzuki, Stille, or Negishi coupling, while the chloro and methoxy functionalities offer orthogonal handling and stability under standard reaction conditions. This compound exhibits excellent bench stability and is well-suited for modular synthesis of heterocyclic scaffolds and API intermediates.

Synthesis

Route1
- 78156-39-5
- ~65%
- In-stock
  
  286947-03-3
References
- Tetrahedron, , vol. 65, # 4 p. 757 - 764
Route2
- In-stock
  
  286946-77-8
- 74-88-4
- ~66%
- In-stock
  
  286947-03-3
References
- US2002/19388 A1, ;
Route3
- In-stock
  
  74115-13-2
- ~%
- In-stock
  
  286947-03-3
References
- Journal of Medicinal Chemistry, , vol. 50, # 15 p. 3627 - 3644

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS05,GHS06
Signal Word : Danger	UN#: 2811
Class : 6.1	Packing Group : Ⅲ
Hazard Statements : H301-H318
Precautionary Statements : P264-P270-P280-P301+P310-P305+P351+P338-P310-P330-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 22.12
LogP 2.5061
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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5-Bromo-2-chloro-3-methoxypyridine

CAS No. 286947-03-3

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