5-Bromo-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

Name: 5-Bromo-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
Brand: ChemScene
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CAS No. 23819-87-6
Cat. No. CS-W014698
Purity≥97%
MDL No.None

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5-Bromo-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile|CS-W014698

Structure of 23819-87-6

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General Information

CAS No. 23819-87-6
Cat. No. CS-W014698
Purity ≥97%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₇BrN₂O
Molecular Weight 227.06
Synonym(s) 5-Bromo-3-Cyano-2-Hydroxy-4,6-Dimethylpyridine
SMILES N#CC1=C(C)C(Br)=C(C)NC1=O

Description

This pyridine derivative features a bromine substituent at the 5-position, flanked by methyl groups at C4 and C6, with a conjugated ketone and nitrile at C2 and C3 respectively. The electron-deficient core enables direct functionalization in cross-coupling and heterocycle synthesis under mild conditions.

Application

5-Bromo-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile serves as a versatile building block in heterocyclic synthesis, enabling efficient access to substituted pyridine scaffolds. Its bromo and nitrile groups facilitate palladium-catalyzed cross-coupling and nucleophilic functionalization, while the methyl substituents enhance stability and modulate reactivity. The compound exhibits excellent bench stability and simplifies purification, making it well-suited for iterative synthesis workflows in medicinal chemistry and process development.

Synthesis

Route1
- In-stock
  
  769-28-8
- ~95%
- In-stock
  
  23819-87-6
References
- Thompson, Wayne J.; Gaudino, John Journal of Organic Chemistry, 1984 , vol. 49, # 26 p. 5237 - 5243
Route2
- 123-54-6
- ~%
- In-stock
  
  23819-87-6
References
- Pharmaceutical Chemistry Journal, , vol. 23, # 12 p. 983 - 986 Khimiko-Farmatsevticheskii Zhurnal, , vol. 23, # 12 p. 1459 - 1463

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS06
Signal Word : Danger	UN#: 3439
Class : 6.1	Packing Group : Ⅲ
Hazard Statements : H302+H312-H315-H319-H331-H335
Precautionary Statements : P264-P270-P330-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 56.65
LogP 1.62592
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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5-Bromo-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

CAS No. 23819-87-6

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