6-Chloro-5-nitropyrimidin-4-amine

Name: 6-Chloro-5-nitropyrimidin-4-amine
Brand: ChemScene
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CAS No. 4316-94-3
Cat. No. CS-W002393
Purity≥98%
MDL No.MFCD00127772

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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-5-nitropyrimidin-4-amine|CS-W002393

Structure of 4316-94-3

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General Information

CAS No. 4316-94-3
Cat. No. CS-W002393
Purity ≥98%
MDL No. MFCD00127772
Storage -20°C, sealed storage, away from moisture and light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₄H₃ClN₄O₂
Molecular Weight 174.55
Synonym(s) Pyrimidine,4-amino-6-chloro-5-nitro- (6CI,7CI,8CI)
SMILES [O-][N+](=O)c1c(N)ncnc1Cl

Description

6-Chloro-5-nitropyrimidin-4-amine features a dual functionalization at the pyrimidine core, combining a chloro group and a nitro substituent flanking a primary amine. This electron-deficient scaffold enables direct coupling in cross-coupling reactions and serves as a key intermediate in medicinal chemistry for constructing heterocyclic pharmacophores.

Application

6-Chloro-5-nitropyrimidin-4-amine serves as a versatile building block in medicinal chemistry, enabling efficient access to pyrimidine-based scaffolds through orthogonal functionalization. The chloro group facilitates nucleophilic substitution, while the nitro and amine functionalities allow for sequential derivatization. Its bench-stable nature and compatibility with standard coupling reactions make it well-suited for modular synthesis of heterocyclic compounds and API intermediates.

Synthesis

Route1
- In-stock
  
  4316-93-2
- ~%
- In-stock
  
  4316-94-3
References
- Baraldi, Pier Giovanni; Broceta, Asier Unciti; Infantas, Maria Jose Pineda De Las; Mochun, Juan Jose Diaz; Espinosa, Antonio; Romagnoli, Romeo Tetrahedron, 2002 , vol. 58, # 38 p. 7607 - 7611
Route2
- 186581-53-3
- 68-12-2
- In-stock
  
  1193-24-4
- ~%
- In-stock
  
  4316-94-3
References
- Lee, Chih-Hung; Daanen, Jerome F; Jiang, Meiqun; Yu, Haixia; Kohlhaas, Kathy L; Alexander, Karen; Jarvis, Michael F; Kowaluk, Elizabeth L; Bhagwat, Shripad S Bioorganic and Medicinal Chemistry Letters, 2001 , vol. 11, # 18 p. 2419 - 2422

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

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Computational Chemistry Data

TPSA 94.94
LogP 0.6204
H_Acceptors 5
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 Pyrimidine compounds

Key Words

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6-Chloro-5-nitropyrimidin-4-amine

CAS No. 4316-94-3

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