2-Amino-4-nitropyridine

Name: 2-Amino-4-nitropyridine
Brand: ChemScene
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CAS No. 4487-50-7
Cat. No. CS-W019623
Purity≥97%
MDL No.MFCD04114148

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Type	HazMat Fee
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FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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General Information

CAS No. 4487-50-7
Cat. No. CS-W019623
Purity ≥97%
MDL No. MFCD04114148
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₅N₃O₂
Molecular Weight 139.11
Synonym(s) 4-Nitropyridin-2-ylamine
SMILES O=[N+](C1=CC(N)=NC=C1)[O-]

Description

2-Amino-4-nitropyridine features a strategically positioned amino group flanked by a nitro substituent on the pyridine ring, creating a potent electron-deficient heterocycle. This combination enables direct incorporation into transition-metal-catalyzed cross-coupling reactions and facilitates rapid derivatization in medicinal chemistry campaigns. The molecule exhibits enhanced solubility in polar solvents and stability under standard bench conditions.

Application

2-Amino-4-nitropyridine serves as a versatile building block in medicinal chemistry, enabling efficient access to nitrogen-containing heterocycles through directed functionalization. Its ortho-amino and nitro groups facilitate sequential transformations, including reduction, coupling, and cyclization reactions, with excellent bench stability and straightforward purification. This compound functions as a key intermediate in the synthesis of pyridine-based API scaffolds and bioactive molecules.

Synthesis

Route1
- 942076-74-6
- ~66%
- In-stock
  
  4487-50-7
References
- Millennium Pharmaceuticals, Inc. Patent: US2012/15942 A1, 2012 ; Location in patent: Page/Page column 51 ; US 20120015942 A1
Route2
- 14432-16-7
- ~%
- In-stock
  
  4487-50-7
References
- MILLENNIUM PHARMACEUTICALS, INC.; GOULD, Alexandra, E.; HARRISON, Sean, J. Patent: WO2011/146591 A1, 2011 ; WO 2011/146591 A1
Route3
- 942076-73-5
- ~%
- In-stock
  
  4487-50-7
References
- Millennium Pharmaceuticals, Inc. Patent: US2012/15942 A1, 2012 ; US 20120015942 A1

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 82.05
LogP 0.572
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Nitro compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

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2-Amino-4-nitropyridine

CAS No. 4487-50-7

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