2-Amino-4-chloro-5-nitropyridine

Name: 2-Amino-4-chloro-5-nitropyridine
Brand: ChemScene
Availability: InStock
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CAS No. 24484-96-6
Cat. No. CS-W003220
Purity≥96%
MDL No.MFCD04973545

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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-Amino-4-chloro-5-nitropyridine|CS-W003220

Structure of 24484-96-6

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General Information

CAS No. 24484-96-6
Cat. No. CS-W003220
Purity ≥96%
MDL No. MFCD04973545
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₄ClN₃O₂
Molecular Weight 173.56
Synonym(s) 4-Chloro-5-nitropyridin-2-amine
SMILES [O-][N+](=O)c1cnc(cc1Cl)N

Description

2-Amino-4-chloro-5-nitropyridine features a fused heterocyclic core bearing complementary reactive handles: a nucleophilic amino group, a chloro substituent for cross-coupling, and a strongly electron-withdrawing nitro group. This combination enables strategic functionalization in synthetic sequences requiring regioselective derivatization under mild conditions.

Application

2-Amino-4-chloro-5-nitropyridine serves as a versatile building block in heterocyclic synthesis, enabling selective functionalization at multiple positions. Its amino and nitro groups provide orthogonal reactivity for sequential transformations, while the chlorine atom facilitates palladium-catalyzed cross-coupling reactions. The compound exhibits good bench stability and is compatible with standard purification methods, making it well-suited for medicinal chemistry campaigns and API intermediate development.

Synthesis

Route1
- In-stock
  
  19798-80-2
- ~29%
- In-stock
  
  6980-08-1
- In-stock
  
  24484-96-6
References
- Tetrahedron Letters, , vol. 53, # 42 p. 5597 - 5601
Route2
- In-stock
  
  19798-80-2
- ~39%
- In-stock
  
  24484-96-6
References
- Wang, Jun; Zhan, Peng; Li, Zhenyu; Liu, Huiqing; De Clercq, Erik; Pannecouque, Christophe; Liu, Xinyong European Journal of Medicinal Chemistry, 2014 , vol. 76, p. 531 - 538
Route3
- In-stock
  
  13091-23-1
- ~33%
- In-stock
  
  24484-96-6
References
- ASTRAZENECA AB; ASTRAZENECA UK LIMITED Patent: WO2006/87530 A1, 2006 ; Location in patent: Page/Page column 73 ; WO 2006/087530 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 1.2254
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Nitro compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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2-Amino-4-chloro-5-nitropyridine

CAS No. 24484-96-6

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