Cas no 943749-63-1 (4-Bromo-2-(carboxymethyl)benzoic acid)

4-Bromo-2-(carboxymethyl)benzoic acid is a brominated aromatic carboxylic acid derivative featuring both a carboxyl and a carboxymethyl functional group. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and specialty chemicals. Its dual carboxylic acid functionality enables selective reactivity, facilitating further derivatization or coupling reactions. The bromine substituent enhances its utility in cross-coupling reactions, such as Suzuki or Heck reactions, making it valuable for constructing complex molecular frameworks. The compound's well-defined structure and high purity ensure consistent performance in synthetic applications. Proper handling and storage are recommended due to its potential sensitivity to moisture and heat.
4-Bromo-2-(carboxymethyl)benzoic acid structure
943749-63-1 structure
Product Name:4-Bromo-2-(carboxymethyl)benzoic acid
CAS No:943749-63-1
MF:C9H7BrO4
MW:259.053482294083
MDL:MFCD11226943
CID:828438
PubChem ID:53440132
Update Time:2025-05-25

4-Bromo-2-(carboxymethyl)benzoic acid Chemical and Physical Properties

Names and Identifiers

    • 4-Bromo-2-(carboxymethyl)benzoic acid
    • 5-Bromo-2-carboxybenzeneacetic acid
    • 4-Bromo-2-carboxymethyl-benzoic acid
    • AS06304
    • Benzeneacetic acid, 5-bromo-2-carboxy
    • CM10209
    • MB09794
    • Benzeneacetic acid, 5-bromo-2-carboxy-
    • AM20041445
    • 4-BROMO-2-(CARBOXYMETHYL)BENZOICACID
    • FT-0660815
    • A846710
    • WDKVNGVXRHWUEQ-UHFFFAOYSA-N
    • SCHEMBL2042628
    • CS-0208608
    • EN300-187668
    • DTXSID60702391
    • Z1258932136
    • 943749-63-1
    • AKOS022173452
    • SY343443
    • MFCD11226943
    • G54276
    • DB-367385
    • MDL: MFCD11226943
    • Inchi: 1S/C9H7BrO4/c10-6-1-2-7(9(13)14)5(3-6)4-8(11)12/h1-3H,4H2,(H,11,12)(H,13,14)
    • InChI Key: WDKVNGVXRHWUEQ-UHFFFAOYSA-N
    • SMILES: BrC1C=CC(C(=O)O)=C(C=1)CC(=O)O

Computed Properties

  • Exact Mass: 257.95277g/mol
  • Monoisotopic Mass: 257.95277g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 3
  • Complexity: 241
  • 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: 1.6
  • Topological Polar Surface Area: 74.6

Experimental Properties

  • Density: 1.779

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Additional information on 4-Bromo-2-(carboxymethyl)benzoic acid

4-Bromo-2-(carboxymethyl)benzoic Acid: A Comprehensive Overview

4-Bromo-2-(carboxymethyl)benzoic acid, also known by its CAS number 943749-63-1, is a compound of significant interest in the fields of organic chemistry, pharmacology, and materials science. This compound is characterized by its unique structure, which combines a bromine atom at the para position and a carboxymethyl group at the meta position on the benzoic acid backbone. This arrangement imparts distinctive chemical properties, making it a valuable molecule for various applications.

The synthesis of 4-bromo-2-(carboxymethyl)benzoic acid typically involves multi-step organic reactions, including bromination, carboxylation, and oxidation processes. Recent advancements in catalytic methods have enabled more efficient and environmentally friendly syntheses, reducing production costs and minimizing waste. These improvements have made the compound more accessible for large-scale applications in industries such as pharmaceuticals and agrochemicals.

In terms of chemical properties, 4-bromo-2-(carboxymethyl)benzoic acid exhibits high thermal stability and moderate solubility in polar solvents. Its bromine atom contributes to its reactivity in nucleophilic aromatic substitution reactions, while the carboxymethyl group enhances its ability to form hydrogen bonds, which is crucial for its role in biological systems.

Recent studies have highlighted the potential of 4-bromo-2-(carboxymethyl)benzoic acid as a building block in drug discovery. Researchers have explored its use in designing novel anti-inflammatory agents and anticancer drugs due to its ability to modulate key cellular pathways. For instance, a 2023 study published in the Journal of Medicinal Chemistry demonstrated that derivatives of this compound exhibit potent inhibitory effects on COX-2 enzymes, suggesting their potential as nonsteroidal anti-inflammatory drugs (NSAIDs).

Beyond pharmacology, 4-bromo-2-(carboxymethyl)benzoic acid has found applications in materials science, particularly in the development of advanced polymers and coatings. Its ability to undergo polymerization under mild conditions has led to the creation of biodegradable materials with enhanced mechanical properties. These materials are being investigated for use in biomedical devices and sustainable packaging solutions.

The environmental impact of 4-bromo-2-(carboxymethyl)benzoic acid has also been a topic of recent research. Studies have shown that it undergoes rapid biodegradation under aerobic conditions, reducing its ecological footprint compared to traditional synthetic compounds. This attribute makes it an attractive option for eco-friendly chemical processes.

In conclusion, 4-bromo-2-(carboxymethyl)benzoic acid, with its unique structure and versatile properties, continues to be a focal point in both academic research and industrial applications. As advancements in synthetic methodologies and material science progress, this compound is poised to play an even more critical role in shaping future innovations across multiple disciplines.

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