2-Chloro-3-nitropyridin-4-amine

Name: 2-Chloro-3-nitropyridin-4-amine
Brand: ChemScene
Availability: InStock
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CAS No. 2789-25-5
Cat. No. CS-D0718
Purity≥98%
MDL No.MFCD07368898

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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-nitropyridin-4-amine|CS-D0718

Structure of 2789-25-5

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General Information

CAS No. 2789-25-5
Cat. No. CS-D0718
Purity ≥98%
MDL No. MFCD07368898
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₄ClN₃O₂
Molecular Weight 173.56
Synonym(s) 4-Amino-2-chloro-3-nitropyridine
SMILES NC1=C(C(Cl)=NC=C1)[N+]([O-])=O

Description

2-Chloro-3-nitropyridin-4-amine features a pyridine core bearing chlorine and nitro groups at adjacent positions, enabling strategic functionalization in heterocyclic synthesis. The amine handle provides direct access to diverse conjugates via coupling reactions. This electron-deficient scaffold offers high reactivity under standard conditions, facilitating efficient incorporation into advanced molecular architectures for medicinal chemistry and materials applications.

Application

2-Chloro-3-nitropyridin-4-amine serves as a versatile building block in medicinal chemistry, enabling efficient construction of heterocyclic scaffolds via palladium-catalyzed cross-coupling and nucleophilic substitution reactions. The ortho-chloro and nitro groups provide complementary reactivity for sequential functionalization, while the amino group offers direct access to diverse amine derivatives. Its bench-stable crystalline form facilitates handling and purification in multi-step synthesis.

Synthesis

Route1
- 14432-13-4
- ~69%
- In-stock
  
  2604-39-9
- In-stock
  
  2789-25-5
References
- Yin, Xueqiang; Schneller, Stewart W Nucleosides, nucleotides and nucleic acids, 2004 , vol. 23, # 1-2 p. 67 - 76
Route2
- In-stock
  
  5975-12-2
- ~69%
- In-stock
  
  2789-25-5
References
- Boehringer Ingelheim Pharma GmbH Co. KG Patent: US2005/20574 A1, 2005 ; Location in patent: Page/Page column 16 ;
Route3
- In-stock
  
  14432-12-3
- ~%
- In-stock
  
  2604-39-9
- In-stock
  
  2789-25-5
References
- Yoo, Euna; Crall, Breanna M.; Balakrishna, Rajalakshmi; Malladi, Subbalakshmi S.; Fox, Lauren M.; Hermanson, Alec R.; David, Sunil A. Organic and Biomolecular Chemistry, 2013 , vol. 11, # 38 p. 6526 - 6545

Safety Information

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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

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2-Chloro-3-nitropyridin-4-amine

CAS No. 2789-25-5

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