5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

Name: 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine
Brand: ChemScene
Availability: InStock
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CAS No. 22276-95-5
Cat. No. CS-W005086
Purity≥95%
MDL No.MFCD09702029

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5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine|CS-W005086

Structure of 22276-95-5

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General Information

CAS No. 22276-95-5
Cat. No. CS-W005086
Purity ≥95%
MDL No. MFCD09702029
Storage -20°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₃BrClN₃
Molecular Weight 232.47
Synonym(s) 7H-Pyrrolo[2,3-d]pyrimidine, 5-bromo-4-chloro-
SMILES C2=C(C1=C(N=CN=C1Cl)[NH]2)Br

Description

5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine delivers a highly reactive heterocyclic scaffold for medicinal chemistry applications. This electron-deficient purine analog integrates readily into kinase inhibitors and nucleoside analogs, offering enhanced metabolic stability. The bromo and chloro substituents enable efficient cross-coupling transformations under mild conditions, facilitating rapid diversification of core structures.

Application

5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine serves as a versatile building block in the synthesis of purine-based scaffolds. Its orthogonal halogenation pattern enables sequential cross-coupling reactions with high regiocontrol, facilitating the construction of biologically relevant heterocycles. The compound exhibits excellent bench stability and is compatible with standard Pd-catalyzed transformations, simplifying purification and scale-up in medicinal chemistry campaigns.

Safety Information

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GHS Pictogram :	GHS No : GHS06
Signal Word : Danger	UN#: 2811
Class : 6.1	Packing Group : Ⅲ
Hazard Statements : H301
Precautionary Statements : P264-P270-P330-P405-P501

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Computational Chemistry Data

TPSA 41.57
LogP 2.3738
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyrrole compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrimidine compounds

Key Words

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5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

CAS No. 22276-95-5

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