5-Bromo-2-chloro-6-methylnicotinonitrile

Name: 5-Bromo-2-chloro-6-methylnicotinonitrile
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CAS No. 84703-18-4
Cat. No. CS-W004423
Purity≥98%
MDL No.MFCD12828072

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5-Bromo-2-chloro-6-methylnicotinonitrile|CS-W004423

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General Information

CAS No. 84703-18-4
Cat. No. CS-W004423
Purity ≥98%
MDL No. MFCD12828072
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₄BrClN₂
Molecular Weight 231.48
Synonym(s) 5-Bromo-2-chloro-6-methylpyridine-3-carbonitrile
SMILES CC1=C(Br)C=C(C(Cl)=N1)C#N

Description

5-Bromo-2-chloro-6-methylnicotinonitrile features a trifunctional pyridine core with complementary reactivity at the bromo, chloro, and nitrile positions. This electron-deficient scaffold enables selective cross-coupling and nucleophilic substitution under mild conditions, offering efficient access to complex heterocyclic architectures in medicinal chemistry and materials synthesis.

Application

5-Bromo-2-chloro-6-methylnicotinonitrile serves as a versatile building block in medicinal chemistry, enabling the construction of substituted pyridine scaffolds via palladium-catalyzed cross-coupling reactions. The molecule’s orthogonal halogenation pattern—bromine at C5 and chlorine at C2—allows for sequential functionalization with high chemoselectivity. The nitrile group provides a handle for downstream transformations, including hydrolysis to carboxylic acids or reduction to aldehydes. Bench-stable and readily purified by column chromatography, it facilitates efficient synthesis of complex heterocyclic intermediates.

Safety Information

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Computational Chemistry Data

TPSA 36.68
LogP 2.6776
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Cyanide/Nitrile

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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5-Bromo-2-chloro-6-methylnicotinonitrile

CAS No. 84703-18-4

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