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CS-W001157 4
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Methyl 6-bromoquinoline-2-carboxylate

  • CAS No. 623583-88-0

  • Cat. No. CS-0099701
  • Molecule weight266.09
  • Purity≥97%
  • MDL No.MFCD08436465

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

Methyl 6-bromoquinoline-2-carboxylate|CS-0099701

Structure of 623583-88-0

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General Information

  • CAS No. 623583-88-0
  • Cat. No. CS-0099701
  • Purity ≥97%
  • MDL No. MFCD08436465
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₈BrNO₂
  • Molecular Weight 266.09
  • Synonym(s) methyl 2-bromoquinoline-6-carboxylate
  • SMILES O=C(C1=NC2=CC=C(Br)C=C2C=C1)OC

Description

Methyl 6-bromoquinoline-2-carboxylate is a bench-stable, moisture-tolerant heterocyclic ester featuring a bromine atom at the 6-position and a methyl carboxylate group at the 2-position. This configuration enables direct functionalization via palladium-catalyzed cross-coupling, facilitating rapid access to complex quinoline derivatives in medicinal chemistry and materials synthesis.

Application

Methyl 6-bromoquinoline-2-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its well-defined bromo and ester functionalities. The molecule exhibits excellent bench stability and facilitates efficient functionalization at the 6-position, supporting the construction of complex quinoline-based scaffolds relevant to medicinal chemistry and materials science.

Synthesis

  • Route1
    • null|null
      67-56-1
    • In-stock
      6-Bromoquinoline-2-carboxylic acid|CS-W003655
      65148-10-9
    • ~85%
    • In-stock
      Methyl 6-bromoquinoline-2-carboxylate|CS-0099701
      623583-88-0

    References

    • SmithKline Beecham Corporation Patent: US2008/96921 A1, 2008 ; Location in patent: Page/Page column 32 ;
  • Route2
    • Methyl 6-bromo-1,2,3,4-tetrahydroquinoline-2-carboxylate|CS-0099700
      511230-72-1
    • ~%
    • In-stock
      Methyl 6-bromoquinoline-2-carboxylate|CS-0099701
      623583-88-0

    References

    • Hulme, Christopher; Ncube, Mghele Vellah; Norman, Mark H.; Ognyanov, Vassil I.; Pettus, Liping H.; Wang, Xianghong; Zhu, Jiawang Patent: US2005/165049 A1, 2005 ; Location in patent: Page/Page column 22 ; US 20050165049 A1
  • Route3

    References

    • MERCK SHARP and DOHME CORP.; LIN, Linus; SOLL, Richard; DONG, Jingchao; WU, Hao; SUZUKI, Takao; HU, Bin; LIU, Dejun; HAO, Jinglai; XU, Ming Patent: WO2011/127643 A1, 2011 ; WO 2011/127643 A1

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

Quality Control

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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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