Cas no 109517-99-9 (5-bromo-2-hydroxybenzene-1,3-dicarbaldehyde)

5-Bromo-2-hydroxybenzene-1,3-dicarbaldehyde is a brominated aromatic dialdehyde compound featuring both aldehyde and hydroxyl functional groups on a benzene ring. Its distinct structure makes it a valuable intermediate in organic synthesis, particularly for constructing heterocyclic frameworks and complex molecular architectures. The presence of the bromo substituent enhances reactivity in cross-coupling reactions, while the hydroxyl and aldehyde groups offer versatile sites for further functionalization. This compound is useful in pharmaceutical and materials chemistry research, where precise control over molecular design is required. Its stability under standard conditions and well-defined reactivity profile contribute to its utility in synthetic applications.
5-bromo-2-hydroxybenzene-1,3-dicarbaldehyde structure
109517-99-9 structure
Product Name:5-bromo-2-hydroxybenzene-1,3-dicarbaldehyde
CAS No:109517-99-9
MF:C8H5BrO3
MW:229.027501821518
CID:1188662
PubChem ID:5260206
Update Time:2025-06-30

5-bromo-2-hydroxybenzene-1,3-dicarbaldehyde Chemical and Physical Properties

Names and Identifiers

    • 5-bromo-2-hydroxybenzene-1,3-dicarbaldehyde
    • ACMC-20mccc
    • 2,6-diformy-4-bromophenol
    • AC1NR2OH
    • CTK0G2401
    • 2-hydroxy-5-bromoisophthalaldehyde
    • 4-bromo-2,6-diformylphenol
    • 1,3-Benzenedicarboxaldehyde, 5-bromo-2-hydroxy-
    • 2,6-diformyl-4-bromophenol
    • 5-bromo-2-hydroxy-1,3-benzenedicarbaldehyde
    • 5-bromo-2-hydroxy-1,3-Benzenedicarboxaldehyde
    • 1,3-Benzenedicarboxaldehyde,5-bromo-2-hydroxy
    • 5-bromo-2-hydroxyisophthalaldehyde
    • SCHEMBL544809
    • 109517-99-9
    • AKOS004121049
    • DB-059917
    • DTXSID90413943
    • 5-Bromo-4-hydroxy-1,3-benzenedicarboxaldehyde
    • 5-bromo-2-hydroxylisophthalaldehyde
    • Inchi: 1S/C8H5BrO3/c9-7-1-5(3-10)8(12)6(2-7)4-11/h1-4,12H
    • InChI Key: OEHFPZMUTXRLFE-UHFFFAOYSA-N
    • SMILES: BrC1C=C(C=O)C(=C(C=O)C=1)O

Computed Properties

  • Exact Mass: 227.94200
  • Monoisotopic Mass: 227.94221g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2
  • Complexity: 165
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.7
  • Topological Polar Surface Area: 54.4?2

Experimental Properties

  • PSA: 54.37000
  • LogP: 1.77970

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5-bromo-2-hydroxybenzene-1,3-dicarbaldehyde Production Method

5-bromo-2-hydroxybenzene-1,3-dicarbaldehyde Related Literature

Additional information on 5-bromo-2-hydroxybenzene-1,3-dicarbaldehyde

5-Bromo-2-Hydroxybenzene-1,3-Dicarbaldehyde: A Comprehensive Overview

5-Bromo-2-Hydroxybenzene-1,3-Dicarbaldehyde, also known by its CAS registry number 109517-99-9, is a versatile aromatic compound with significant applications in organic synthesis and material science. This compound, characterized by its bromine atom at position 5, hydroxyl group at position 2, and two aldehyde groups at positions 1 and 3 on the benzene ring, has garnered attention due to its unique reactivity and potential in various chemical transformations.

The structure of 5-Bromo-2-Hydroxybenzene-1,3-Dicarbaldehyde lends itself to a wide range of chemical reactions. The presence of aldehyde groups makes it an excellent substrate for condensation reactions, such as the aldol reaction and the Perkin reaction. These reactions are pivotal in the synthesis of complex organic molecules, including pharmaceuticals and agrochemicals. Recent studies have highlighted its utility in the construction of heterocyclic compounds, which are integral to drug design.

One of the most notable advancements involving this compound is its role in the synthesis of fluorescent materials. Researchers have exploited the electron-withdrawing effects of the aldehyde groups and the directing effects of the hydroxyl group to create novel materials with enhanced optical properties. These materials have potential applications in bioimaging and sensing technologies.

In addition to its synthetic applications, 5-Bromo-2-Hydroxybenzene-1,3-Dicarbaldehyde has been studied for its biological activity. Recent investigations have revealed that this compound exhibits moderate antioxidant properties, which could be harnessed in the development of nutraceuticals or cosmeceuticals. Furthermore, its ability to coordinate with metal ions has led to explorations in catalysis and metallopharmaceuticals.

The synthesis of 5-Bromo-2-Hydroxybenzene-1,3-Dicarbaldehyde typically involves multi-step processes that require precise control over reaction conditions to ensure high yields and purity. Modern synthetic strategies often incorporate green chemistry principles, such as using microwave-assisted synthesis or catalytic systems to minimize environmental impact.

In conclusion, 5-Bromo-2-Hydroxybenzene-1,3-Dicarbaldehyde stands as a testament to the diversity and utility of aromatic compounds in contemporary chemistry. Its unique structure continues to inspire innovative research across multiple disciplines, underscoring its importance as a valuable building block in organic synthesis.

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