5-Bromo-4-chloro-2-pyrimidinamine

Name: 5-Bromo-4-chloro-2-pyrimidinamine
Brand: ChemScene
Availability: InStock
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CAS No. 1044767-99-8
Cat. No. CS-W008664
Purity≥96%
MDL No.MFCD11046979

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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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5-Bromo-4-chloro-2-pyrimidinamine|CS-W008664

Structure of 1044767-99-8

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General Information

CAS No. 1044767-99-8
Cat. No. CS-W008664
Purity ≥96%
MDL No. MFCD11046979
Storage -20°C, sealed storage, away from moisture and light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₄H₃BrClN₃
Molecular Weight 208.44
Synonym(s) 2-Amino-5-bromo-4-chloropyrimidine; 5-Bromo-4-chloropyrimidin-2-amine; 5-bromo-4-chloro-pyrimidin-2-amine
SMILES NC1=NC=C(Br)C(Cl)=N1

Description

5-Bromo-4-chloro-2-pyrimidinamine delivers a dual halogenated pyrimidine scaffold with high reactivity in cross-coupling and nucleophilic substitution reactions. The electron-deficient ring, flanked by bromo and chloro substituents at C5 and C4, enables selective functionalization under palladium catalysis. This bench-stable derivative integrates readily into heterocyclic architectures for medicinal chemistry and materials synthesis.

Application

5-Bromo-4-chloro-2-pyrimidinamine serves as a versatile building block in medicinal chemistry, enabling efficient access to substituted pyrimidine scaffolds via palladium-catalyzed cross-coupling reactions. The strategically positioned bromo and chloro groups exhibit orthogonal reactivity, facilitating sequential functionalization. Its stability under standard reaction conditions and compatibility with diverse coupling partners make it ideal for constructing complex heterocyclic systems relevant to kinase inhibitor and antiviral drug discovery.

Synthesis

Route1
- In-stock
  
  3993-78-0
- ~85%
- In-stock
  
  1044767-99-8
References
- Leahy, James W.; Buhr, Chris A.; Johnson, Henry W. B.; Kim, Byung Gyu; Baik, Taegon; Cannoy, Jonah; Forsyth, Timothy P.; Jeong, Joon Won; Lee, Matthew S.; Ma, Sunghoon; Noson, Kevin; Wang, Longcheng; Williams, Matthew; Nuss, John M.; Brooks, Eric; Foster, Paul; Goon, Leanne; Heald, Nathan; Holst, Charles; Jaeger, Christopher; Lam, Scott; Lougheed, Julie; Nguyen, Lam; Plonowski, Arthur; Song, Joanne; Stout, Thomas; Wu, Xiang; Yakes, Michael F.; Yu, Peiwen; Zhang, Wentao; Lamb, Peter; Raeber, Olivia Journal of Medicinal Chemistry, 2012 , vol. 55, # 11 p. 5467 - 5482

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07,GHS09
Signal Word : Warning	UN#: 3077
Class : 9	Packing Group : Ⅲ
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 1.4747
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyrimidine compounds

Key Words

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5-Bromo-4-chloro-2-pyrimidinamine

CAS No. 1044767-99-8

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