Cas no 108857-24-5 (2-Amino-5-iodo-3-methylbenzoic acid)

2-Amino-5-iodo-3-methylbenzoic acid is a halogenated benzoic acid derivative featuring an amino group at the 2-position and an iodine substituent at the 5-position, with a methyl group at the 3-position. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and specialty chemicals. The presence of both amino and carboxyl groups allows for further functionalization, while the iodine atom enables cross-coupling reactions, such as Suzuki or Sonogashira couplings. Its well-defined structure and reactivity make it valuable for constructing complex molecular frameworks. The compound is typically handled under controlled conditions due to its sensitivity to light and moisture.
2-Amino-5-iodo-3-methylbenzoic acid structure
108857-24-5 structure
Product Name:2-Amino-5-iodo-3-methylbenzoic acid
CAS No:108857-24-5
MF:C8H8INO2
MW:277.059094429016
MDL:MFCD09029816
CID:128189
PubChem ID:11231233
Update Time:2025-05-20

2-Amino-5-iodo-3-methylbenzoic acid Chemical and Physical Properties

Names and Identifiers

    • 2-Amino-5-iodo-3-methylbenzoic acid
    • 2-Amino-5-iodo-3-methylbenzenecarboxylic acid
    • Benzoic acid,2-amino-5-iodo-3-methyl-
    • 2-amino-3-methyl-5-iodobenzoic acid
    • 2-amino-5-iodo-3-methyl-benzoic acid
    • 2-Amino-5-jod-3-methyl-benzoesaeure
    • 5-Jod-2-amino-m-toluylsaeure
    • ACMC-1CAD3
    • AGN-PC-004VHH
    • aminoiodomethylbenzenecarboxylicacid
    • CTK4A6216
    • SureCN857080
    • AC-17770
    • FT-0681300
    • HD-0722
    • CS-0149159
    • AKOS005073042
    • 108857-24-5
    • MFCD09029816
    • SB81373
    • WFKOJKHXWWNXPK-UHFFFAOYSA-N
    • AT30290
    • J-507951
    • DTXSID80459552
    • SCHEMBL857080
    • SY333429
    • DB-104232
    • 2-Amino-5-iodo-3-methylbenzoicacid
    • MDL: MFCD09029816
    • Inchi: 1S/C8H8INO2/c1-4-2-5(9)3-6(7(4)10)8(11)12/h2-3H,10H2,1H3,(H,11,12)
    • InChI Key: WFKOJKHXWWNXPK-UHFFFAOYSA-N
    • SMILES: IC1C=C(C(=O)O)C(=C(C)C=1)N

Computed Properties

  • Exact Mass: 276.95954
  • Monoisotopic Mass: 276.95998g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 186
  • 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: 3.9
  • Topological Polar Surface Area: 63.3?2

Experimental Properties

  • Melting Point: 235-240°
  • PSA: 63.32
  • LogP: 2.46120

2-Amino-5-iodo-3-methylbenzoic acid Security Information

  • HazardClass:IRRITANT

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Additional information on 2-Amino-5-iodo-3-methylbenzoic acid

2-Amino-5-Iodo-3-Methylbenzoic Acid: A Comprehensive Overview

2-Amino-5-Iodo-3-Methylbenzoic Acid, also known by its CAS registry number CAS No. 108857-24-5, is a compound of significant interest in the fields of organic chemistry, pharmacology, and materials science. This compound, with its unique structure featuring an amino group, an iodo substituent, and a methyl group attached to a benzoic acid backbone, has garnered attention due to its potential applications in drug development and as a building block for advanced materials.

The molecular structure of 2-Amino-5-Iodo-3-Methylbenzoic Acid is characterized by a benzene ring with three substituents: an amino group (-NH?) at the 2-position, an iodine atom at the 5-position, and a methyl group (-CH?) at the 3-position. The carboxylic acid group (-COOH) is located at the para position relative to the amino group. This arrangement creates a molecule with unique electronic properties and reactivity, making it a valuable substrate for various chemical transformations.

Recent studies have highlighted the importance of iodine-containing aromatic compounds in medicinal chemistry. The presence of the iodo group in 2-Amino-5-Iodo-3-Methylbenzoic Acid allows for potential applications in radiotherapy and imaging due to iodine's role as a radioactive tracer in nuclear medicine. Additionally, the amino and methyl groups provide opportunities for further functionalization, enabling the synthesis of derivatives with enhanced biological activity or solubility.

In terms of synthesis, 2-Amino-5-Iodo-3-Methylbenzoic Acid can be prepared through a variety of methods, including electrophilic aromatic substitution and coupling reactions. Researchers have explored efficient routes to this compound, often leveraging modern catalytic techniques to improve yields and reduce reaction times. For instance, recent advancements in palladium-catalyzed cross-coupling reactions have provided novel pathways for constructing the iodo-substituted aromatic ring.

The biological activity of 2-Amino-5-Iodo-3-Methylbenzoic Acid has been a focal point of recent investigations. Studies have demonstrated that this compound exhibits potential anti-inflammatory and antioxidant properties, making it a candidate for further exploration in therapeutic applications. Moreover, its ability to act as a precursor for more complex molecules has positioned it as a key intermediate in drug discovery pipelines.

In the realm of materials science, 2-Amino-5-Iodo-3-Methylbenzoic Acid has shown promise as a component in advanced materials such as conductive polymers and metal-organic frameworks (MOFs). The functional groups present in this compound enable strong interactions with metal ions, which is critical for the formation of stable MOFs with applications in gas storage and catalysis.

The integration of computational chemistry tools has further enhanced our understanding of 2-Amino-5-Iodo-3-Methylbenzoic Acid. Quantum mechanical calculations have provided insights into its electronic structure and reactivity, aiding in the design of more efficient synthetic routes and predictive modeling of its behavior in different chemical environments.

In conclusion, CAS No. 108857-24-5, or 2-Amino-5-Iodo-3-Methylbenzoic Acid, stands out as a versatile compound with diverse applications across multiple disciplines. Its unique structure and functional groups make it an invaluable tool for researchers seeking to develop innovative solutions in medicine, materials science, and beyond. As ongoing research continues to uncover new properties and uses for this compound, its significance within the scientific community is likely to grow further.

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