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Methyl 8-bromoquinoline-2-carboxylate

  • CAS No. 1242446-32-7

  • Cat. No. CS-0498490
  • Purity≥98%
  • MDL No.None

*For research and further manufacturing use only, not for direct human use.

Methyl 8-bromoquinoline-2-carboxylate|CS-0498490

Structure of 1242446-32-7

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General Information

  • CAS No. 1242446-32-7
  • Cat. No. CS-0498490
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₈BrNO₂
  • Molecular Weight 266.09
  • Synonym(s) 8-Bromo-quinoline-2-carboxylic acid methyl ester
  • SMILES O=C(C1=NC2=C(Br)C=CC=C2C=C1)OC

Description

Methyl 8-bromoquinoline-2-carboxylate is a brominated quinoline ester featuring a strategically positioned bromine at the 8-position and a methyl carboxylate group at C2. This configuration enables direct functionalization in cross-coupling reactions, serving as a key intermediate in medicinal chemistry. The electron-deficient heterocyclic core enhances reactivity in Pd-catalyzed transformations, while the ester moiety offers tunable polarity for downstream derivatization.

Application

Methyl 8-bromoquinoline-2-carboxylate serves as a versatile building block in medicinal chemistry and heterocyclic synthesis. The bromine at the C8 position enables palladium-catalyzed cross-coupling reactions, while the quinoline core provides a rigid, planar scaffold with favorable pharmacophoric properties. The methyl ester group offers a handle for selective derivatization, including hydrolysis or reduction, facilitating downstream functionalization. Bench-stable and readily purified by column chromatography, it functions effectively in standard synthetic workflows involving nucleophilic substitution, metal-catalyzed coupling, and ring functionalization.

Safety Information

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GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362

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Computational Chemistry Data

  • TPSA   39.19
  • LogP   2.7839
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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