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CS-W001157 4
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3-Bromobenzene-1,2-diol

  • CAS No. 14381-51-2

  • Cat. No. CS-W006003
  • Purity≥97%
  • MDL No.MFCD00869768

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

3-Bromobenzene-1,2-diol|CS-W006003

Structure of 14381-51-2

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General Information

  • CAS No. 14381-51-2
  • Cat. No. CS-W006003
  • Purity ≥97%
  • MDL No. MFCD00869768
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅BrO₂
  • Molecular Weight 189.01
  • Synonym(s) 3-Bromocatechol
  • SMILES C1=CC=C(Br)C(=C1O)O

Description

3-Bromobenzene-1,2-diol features a bromine substituent at the meta position relative to a vicinal diol system, delivering enhanced reactivity in electrophilic substitution and enabling selective functionalization. The ortho-diol moiety facilitates chelation and stabilization in transition metal-catalyzed transformations. This compound serves as a valuable intermediate in the synthesis of bioactive heterocycles and complex aromatic scaffolds.

Application

3-Bromobenzene-1,2-diol serves as a versatile ortho-dihydroxy building block for the synthesis of bioactive heterocycles and functionalized aromatics. Its bromine substituent enables palladium-catalyzed cross-coupling reactions, while the adjacent hydroxyl groups facilitate directed metalation, electrophilic substitution, or protection strategies. The compound exhibits good bench stability and is readily purified by standard chromatographic methods, making it well-suited for iterative synthetic sequences in medicinal chemistry and materials development.

Synthesis

  • Route1

    References

    • Stephan, Michel; Zupancic, Borut; Mohar, Barbara Tetrahedron, 2011 , vol. 67, # 34 p. 6308 - 6315
  • Route2

    References

    • Corvas International, Inc. Patent: US6342504 B1, 2002 ; Location in patent: Page column 123 ; US 6342504 B1
  • Route3

    References

    • Kobayashi, Yuichi; Lalitnorasate, Paveena; Kaneko, Yuki; Kiyotsuka, Yohei; Endo, Yoshiki Tetrahedron Letters, 2010 , vol. 51, # 46 p. 6018 - 6021

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   40.46
  • LogP   1.8603
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   0

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