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CS-W001157 4
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5-Bromoisophthalaldehyde

  • CAS No. 120173-41-3

  • Cat. No. CS-W006569
  • Purity≥97%
  • MDL No.MFCD08690086

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

5-Bromoisophthalaldehyde|CS-W006569

Structure of 120173-41-3

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General Information

  • CAS No. 120173-41-3
  • Cat. No. CS-W006569
  • Purity ≥97%
  • MDL No. MFCD08690086
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅BrO₂
  • Molecular Weight 213.03
  • Synonym(s) 5-bromoisophthaldehyde
  • SMILES O=CC1=CC(Br)=CC(C=O)=C1

Description

5-Bromoisophthalaldehyde features a brominated aromatic ring paired with two aldehyde functionalities in a rigid ortho-configuration, enabling selective coupling in cross-coupling and conjugation chemistries. This electron-deficient scaffold facilitates efficient incorporation into bioconjugates, fluorescent probes, and functionalized polymers under standard conditions.

Application

5-Bromoisophthalaldehyde serves as a versatile building block in synthetic organic chemistry, enabling the construction of functionalized heterocycles and pharmaceutical intermediates. Its ortho-dialdehyde architecture provides two reactive aldehyde groups for condensation reactions, while the bromine substituent offers a handle for subsequent cross-coupling transformations. The compound exhibits good bench stability and facilitates straightforward purification, making it well-suited for iterative synthesis workflows in medicinal chemistry and materials science.

Synthesis

  • Route1

    References

    • Catala, Laure; Turek, Philippe; Le Moigne, Jacques; De Cian, Andre; Kyritsakas, Nathalie Tetrahedron Letters, 2000 , vol. 41, # 7 p. 1015 - 1018
  • Route2

    References

    • Blackburn, Octavia A.; Coe, Benjamin J.; Helliwell, Madeleine; Raftery, James Organometallics, 2012 , vol. 31, # 15 p. 5307 - 5320
  • Route3
    • In-stock
      1,3,5-Tribromobenzene|CS-0019382
      626-39-1
    • null|null
      68-12-2
    • ~85%
    • In-stock
      5-Bromoisophthalaldehyde|CS-W006569
      120173-41-3

    References

    • Matsuda, Kenji; Inoue, Katsuya; Koga, Noboru; Nakamura, Nobuo; Iwamura, Hiizu Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1994 , vol. 253, p. 33 - 40

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 : 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   34.14
  • LogP   2.0741
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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