2,5-Dichloropyrimidin-4-amine

Name: 2,5-Dichloropyrimidin-4-amine
Brand: ChemScene
Availability: InStock
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CAS No. 89180-51-8
Cat. No. CS-W003854
Purity≥97%
MDL No.MFCD13191633

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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2,5-Dichloropyrimidin-4-amine|CS-W003854

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General Information

CAS No. 89180-51-8
Cat. No. CS-W003854
Purity ≥97%
MDL No. MFCD13191633
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₄H₃Cl₂N₃
Molecular Weight 163.99
Synonym(s) 4-Amino-2,5-dichloropyrimidine
SMILES Clc1ncc(c(n1)N)Cl

Description

2,5-Dichloropyrimidin-4-amine serves as a pivotal heterocyclic scaffold in medicinal chemistry, featuring two chlorine substituents that enhance electrophilic reactivity at the pyrimidine ring. This compound integrates readily into kinase inhibitors and antiviral agents due to its ability to form stable covalent adducts with nucleophilic residues. The amine functionality enables straightforward conjugation via amidation or coupling reactions, facilitating modular synthesis of targeted therapeutics under standard conditions.

Application

2,5-Dichloropyrimidin-4-amine serves as a versatile building block in medicinal chemistry, enabling efficient construction of kinase inhibitors and other bioactive heterocycles. The dichloro substitution pattern facilitates selective nucleophilic displacement at C2 or C5, while the primary amine group supports direct coupling or derivatization. Its bench-stable nature and compatibility with standard cross-coupling protocols make it ideal for modular synthesis workflows.

Synthesis

Route1
- In-stock
  
  5750-76-5
- ~78%
- In-stock
  
  89180-51-8
References
- Barlaam, Bernard; Fennell, Mike; Germain, Herve; Green, Tim; Hennequin, Laurent; Morgentin, Remy; Olivier, Annie; Ple, Patrick; Vautier, Michel; Costello, Gerard Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 24 p. 5446 - 5449

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 51.8
LogP 1.3656
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Skeleton Aromatic heterocycle compounds Pyrimidine compounds

Key Words

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2,5-Dichloropyrimidin-4-amine

CAS No. 89180-51-8

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