6-Chloro-3-nitropyridin-2(1H)-one

Name: 6-Chloro-3-nitropyridin-2(1H)-one
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 92138-35-7
Cat. No. CS-W006247
Purity≥98%
MDL No.MFCD05261002

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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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6-Chloro-3-nitropyridin-2(1H)-one|CS-W006247

Structure of 92138-35-7

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General Information

CAS No. 92138-35-7
Cat. No. CS-W006247
Purity ≥98%
MDL No. MFCD05261002
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₃ClN₂O₃
Molecular Weight 174.54
Synonym(s) 6-Chloro-3-nitropyridin-2-ol
SMILES O=C1C([N+]([O-])=O)=CC=C(Cl)N1

Description

6-Chloro-3-nitropyridin-2(1H)-one features a fused heterocyclic core with complementary electron-deficient and halogenated functionalities. This configuration enables direct incorporation into synthetic scaffolds via cross-coupling or nucleophilic substitution reactions under standard conditions. The compound exhibits bench-stable handling characteristics and facilitates efficient access to bioactive pyridinone derivatives in medicinal chemistry workflows.

Application

6-Chloro-3-nitropyridin-2(1H)-one serves as a versatile building block in medicinal chemistry, enabling efficient access to nitrogen-containing heterocycles via palladium-catalyzed cross-coupling and nucleophilic substitution reactions. The ortho-chloro and nitro groups provide complementary reactivity for sequential functionalization, while the pyridinone scaffold offers enhanced solubility and metabolic stability in bioactive molecules. Its bench-stable crystalline form facilitates handling and purification in multi-step syntheses.

Synthesis

Route1
- In-stock
  
  27048-04-0
- ~79%
- In-stock
  
  92138-35-7
References
- ASTRAZENECA AB; ASTRAZENECA UK LIMITED Patent: WO2009/27732 A1, 2009 ; Location in patent: Page/Page column 70 ; WO 2009/027732 A1
Route2
- In-stock
  
  16013-85-7
- ~%
- In-stock
  
  92138-35-7
References
- Angewandte Chemie - International Edition, , vol. 42, # 5 p. 535 - 539

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

Quality Control

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Computational Chemistry Data

TPSA 76
LogP 0.9365
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Nitro compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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6-Chloro-3-nitropyridin-2(1H)-one

CAS No. 92138-35-7

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