Methyl 5-bromo-1,4-dihydro-4-oxo-3-pyridinecarboxylate

Name: Methyl 5-bromo-1,4-dihydro-4-oxo-3-pyridinecarboxylate
Brand: ChemScene
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CAS No. 1175512-08-9
Cat. No. CS-W022864
Molecule weight232.03
Purity≥97%
MDL No.MFCD26383572

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Methyl 5-bromo-1,4-dihydro-4-oxo-3-pyridinecarboxylate|CS-W022864

Structure of 1175512-08-9

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General Information

CAS No. 1175512-08-9
Cat. No. CS-W022864
Purity ≥97%
MDL No. MFCD26383572
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₆BrNO₃
Molecular Weight 232.03
Synonym(s) 3-Pyridinecarboxylic acid, 5-bromo-1,4-dihydro-4-oxo-, methyl ester
SMILES O=C(C1=CNC=C(Br)C1=O)OC

Description

Methyl 5-bromo-1,4-dihydro-4-oxo-3-pyridinecarboxylate features a brominated pyridinone scaffold with a methyl ester group, enabling direct functionalization at the C5 position. This bench-stable reagent integrates readily into transition-metal-catalyzed cross-coupling reactions and serves as a key intermediate in synthesizing bioactive heterocycles.

Application

Methyl 5-bromo-1,4-dihydro-4-oxo-3-pyridinecarboxylate serves as a versatile building block in heterocyclic synthesis, enabling direct functionalization at the C5 position via transition-metal-catalyzed cross-coupling reactions. The bromo group exhibits high reactivity in Pd-catalyzed coupling processes, while the pyridone core provides orthogonal functionality for further derivatization. Bench-stable and readily purified by column chromatography, it facilitates efficient access to substituted pyridinones relevant to medicinal chemistry and agrochemical development.

Synthesis

Route1
- 67-56-1
- In-stock
  
  1052114-83-6
- ~92%
- In-stock
  
  1175512-08-9
References
- Kyoung, Soon Kim; Zhang, Liping; Schmidt, Robert; Cai, Zhen-Wei; Wei, Donna; Williams, David K.; Lombardo, Louis J.; Trainor, George L.; Xie, Dianlin; Zhang, Yaquan; An, Yongmi; Sack, John S.; Tokarski, John S.; Darienzo, Celia; Kamath, Amrita; Marathe, Punit; Zhang, Yueping; Lippy, Jonathan; Jeyaseelan Sr., Robert; Wautlet, Barri; Henley, Benjamin; Gullo-Brown, Johnni; Manne, Veeraswamy; Hunt, John T.; Fargnoli, Joseph; Borzilleri, Robert M. Journal of Medicinal Chemistry, 2008 , vol. 51, # 17 p. 5330 - 5341

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 59.42
LogP 1.3363
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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Methyl 5-bromo-1,4-dihydro-4-oxo-3-pyridinecarboxylate

CAS No. 1175512-08-9

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