2-Chloro-3-nitro-6-methoxypyridine

Name: 2-Chloro-3-nitro-6-methoxypyridine
Brand: ChemScene
Availability: InStock
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CAS No. 38533-61-8
Cat. No. CS-W020694
Purity≥98%
MDL No.MFCD00130268

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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-Chloro-3-nitro-6-methoxypyridine|CS-W020694

Structure of 38533-61-8

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General Information

CAS No. 38533-61-8
Cat. No. CS-W020694
Purity ≥98%
MDL No. MFCD00130268
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₅ClN₂O₃
Molecular Weight 188.57
Synonym(s) 2-Chloro-6-methoxy-3-nitropyridine
SMILES COC1=CC=C(C(Cl)=N1)[N+]([O-])=O

Description

2-Chloro-3-nitro-6-methoxypyridine features a pyridine core functionalized with chlorine, nitro, and methoxy groups at the 2-, 3-, and 6-positions, respectively. This electron-deficient heterocycle serves as a key intermediate in medicinal chemistry, enabling direct coupling reactions under standard conditions. The ortho-chloro and nitro substituents facilitate palladium-catalyzed cross-coupling, while the methoxy group enhances solubility and modulates electronic properties.

Application

2-Chloro-3-nitro-6-methoxypyridine serves as a versatile building block in heterocyclic synthesis, enabling efficient construction of pyridine-based scaffolds via palladium-catalyzed cross-coupling reactions. The chloro group facilitates reliable C–C bond formation under standard Suzuki or Negishi conditions, while the nitro and methoxy substituents provide orthogonal reactivity for sequential functionalization. Bench-stable and amenable to purification by flash chromatography, it supports scalable, high-yield transformations in medicinal chemistry and process development workflows.

Synthesis

Route1
- In-stock
  
  17228-64-7
- ~81%
- In-stock
  
  38533-61-8
References
- Rutgerswerke Aktiengesellschaft Patent: US4529800 A1, 1985 ;
Route2
- 67-56-1
- In-stock
  
  16013-85-7
- ~%
- In-stock
  
  40851-91-0
- In-stock
  
  38533-61-8
- 18677-41-3
References
- Yap, Jeremy L.; Hom, Kellie; Fletcher, Steven Tetrahedron Letters, 2011 , vol. 52, # 32 p. 4172 - 4176

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-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 65.26
LogP 1.6518
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Nitro compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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2-Chloro-3-nitro-6-methoxypyridine

CAS No. 38533-61-8

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