Methyl 7-bromoquinoline-4-carboxylate

Name: Methyl 7-bromoquinoline-4-carboxylate
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CAS No. 220844-76-8
Cat. No. CS-B0599
Purity≥98%
MDL No.MFCD11976157

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Methyl 7-bromoquinoline-4-carboxylate|CS-B0599

Structure of 220844-76-8

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General Information

CAS No. 220844-76-8
Cat. No. CS-B0599
Purity ≥98%
MDL No. MFCD11976157
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₈BrNO₂
Molecular Weight 266.09
Synonym(s) 4-Quinolinecarboxylic acid, 7-broMo-, Methyl ester
SMILES O=C(C1=CC=NC2=CC(Br)=CC=C12)OC

Description

Methyl 7-bromoquinoline-4-carboxylate is a bench-stable, moisture-tolerant heterocyclic ester featuring a bromine atom at the C7 position and a methyl carboxylate group at C4. This electronic configuration enables efficient cross-coupling reactions, particularly in palladium-catalyzed transformations. The para-substituted quinoline scaffold provides enhanced solubility and stability under standard reaction conditions, facilitating integration into complex molecular architectures.

Application

Methyl 7-bromoquinoline-4-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions at the C7 position. The quinoline scaffold provides inherent stability and π-conjugation, while the bromide facilitates functionalization via Suzuki, Stille, or Negishi couplings. The methyl ester group offers compatibility with standard reduction and hydrolysis protocols, allowing access to carboxylic acid derivatives. This compound exhibits excellent bench stability and is readily purified by flash chromatography, making it well-suited for iterative synthetic sequences in medicinal chemistry and materials science applications.

Synthesis

Route1
- 67-56-1
- In-stock
  
  31009-04-8
- ~%
- In-stock
  
  220844-76-8
References
- SmithKline Beecham Corporation Patent: US2008/96921 A1, 2008 ; Location in patent: Page/Page column 37-38 ;

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-P280-P302+P352

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Computational Chemistry Data

TPSA 39.19
LogP 2.7839
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds quinoline compounds

Key Words

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Methyl 7-bromoquinoline-4-carboxylate

CAS No. 220844-76-8

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