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CS-W001157 4
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3-Bromo-1-naphthoic acid

  • CAS No. 16726-66-2

  • Cat. No. CS-0139704
  • Purity≥97%
  • MDL No.None

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

3-Bromo-1-naphthoic acid|CS-0139704

Structure of 16726-66-2

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General Information

  • CAS No. 16726-66-2
  • Cat. No. CS-0139704
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₇BrO₂
  • Molecular Weight 251.08
  • Synonym(s) 3-bromonaphthalene-1-carboxylic Acid
  • SMILES O=C(O)C1=C2C=CC=CC2=CC(Br)=C1

Description

3-Bromo-1-naphthoic acid features a bromine substituent at the 3-position of the naphthalene core, enhancing electrophilic reactivity and enabling direct functionalization in cross-coupling processes. The carboxylic acid group provides a handle for derivatization via esterification, amidation, or salt formation. This bench-stable compound serves as a key intermediate in the synthesis of bioactive naphthyl derivatives and functional materials.

Application

3-Bromo-1-naphthoic acid serves as a versatile building block in synthetic organic chemistry, enabling direct functionalization at the naphthalene ring and facilitating subsequent cross-coupling reactions. Its bromine substituent provides high reactivity in palladium-catalyzed transformations, while the carboxylic acid group offers orthogonal functionality for derivatization. The compound exhibits excellent bench stability and is readily purified by recrystallization, making it ideal for iterative synthesis of complex heterocycles and pharmaceutical intermediates.

Synthesis

  • Route1

    References

    • PRESIDENT AND FELLOWS OF HARVARD COLLEGE; CHOREV, Michael; AKTAS, Bertal Huseyin; HALPERIN, Jose A.; WAGNER, Gerhard Patent: WO2012/6068 A2, 2012 ; Location in patent: Page/Page column 70-71 ;
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    References

    • TAKEDA GMBH; HOFFMEYER, Angelika; BOER, Rainer; HEßMANN, Manuela; PAHL, Andreas; DUNKERN, Torsten; HARTUNG, Simone; ZITT, Christof; VOLZ, Jürgen; PRÄCHTER, Christiane; MAKHIJA, Mahindra; JAIN, Hiteshkumar; GAVADE, Sandip; PRABHU, Arati; TIWARI, Manojkumar; KECHE, Ashish; PATEL, Sarvesh Patent: WO2013/164326 A1, 2013 ; Location in patent: Page/Page column 19; 20 ;
  • Route3
    • null|null
      6314-27-8
    • ~%
    • In-stock
      3-Bromo-1-naphthoic acid|CS-0139704
      16726-66-2

    References

    • WO2011/159067 A2, ; Page/Page column 54 ; WO 2011/159067 A2

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   37.3
  • LogP   3.3005
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   1

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