Cas no 211308-80-4 (Methyl 6-Amino-5-iodopyridine-3-carboxylate)

Methyl 6-Amino-5-iodopyridine-3-carboxylate is a versatile heterocyclic compound featuring both amino and iodo functional groups on a pyridine scaffold, along with a methyl ester moiety. This structure makes it a valuable intermediate in organic synthesis, particularly for constructing complex pharmaceuticals and agrochemicals. The iodine substituent offers a reactive site for cross-coupling reactions, such as Suzuki or Sonogashira couplings, while the amino group enables further derivatization. The methyl ester enhances solubility and facilitates hydrolysis or transesterification. Its well-defined reactivity and stability under standard conditions make it suitable for use in medicinal chemistry and material science applications.
Methyl 6-Amino-5-iodopyridine-3-carboxylate structure
211308-80-4 structure
Product Name:Methyl 6-Amino-5-iodopyridine-3-carboxylate
CAS No:211308-80-4
MF:C7H7IN2O2
MW:278.047153711319
MDL:MFCD16660021
CID:1028471
PubChem ID:15350913
Update Time:2025-11-02

Methyl 6-Amino-5-iodopyridine-3-carboxylate Chemical and Physical Properties

Names and Identifiers

    • Methyl 6-amino-5-iodonicotinate
    • Methyl 6-amino-5-iodonicotite
    • (ii)-6-Amino-5-iodo-nicotinic acid methyl ester
    • 6-AMINO-5-IODO-NICOTINIC ACID METHYL ESTER
    • QC-8622
    • AKOS015996941
    • methyl 6-amino-5-iodo-pyridine-3-carboxylate
    • LG-0703
    • SCHEMBL836245
    • Methyl6-amino-5-iodonicotinate
    • D74443
    • CS-0082262
    • 3-Pyridinecarboxylic acid, 6-amino-5-iodo-, methyl ester
    • 211308-80-4
    • MFCD16660021
    • DA-43277
    • DTXSID80571849
    • methyl 6-amino-5-iodopyridine-3-carboxylate
    • CJSCVGMGFVSANX-UHFFFAOYSA-N
    • SY284481
    • Methyl 6-Amino-5-iodopyridine-3-carboxylate
    • MDL: MFCD16660021
    • Inchi: 1S/C7H7IN2O2/c1-12-7(11)4-2-5(8)6(9)10-3-4/h2-3H,1H3,(H2,9,10)
    • InChI Key: CJSCVGMGFVSANX-UHFFFAOYSA-N
    • SMILES: IC1C(N)=NC=C(C(=O)OC)C=1

Computed Properties

  • Exact Mass: 277.95500
  • Monoisotopic Mass: 277.95523g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2
  • Complexity: 177
  • 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
  • Topological Polar Surface Area: 65.2?2

Experimental Properties

  • PSA: 65.21000
  • LogP: 1.63620

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Methyl 6-Amino-5-iodopyridine-3-carboxylate Production Method

Additional information on Methyl 6-Amino-5-iodopyridine-3-carboxylate

Methyl 6-Amino-5-iodopyridine-3-carboxylate (CAS No. 211308-80-4): A Key Intermediate in Modern Pharmaceutical Synthesis

Methyl 6-Amino-5-iodopyridine-3-carboxylate, identified by its CAS number 211308-80-4, is a highly valuable intermediate in the realm of pharmaceutical synthesis. This compound, characterized by its pyridine core structure modified with an amino group at the 6-position, an iodine atom at the 5-position, and a carboxylate ester at the 3-position, has garnered significant attention due to its versatile applications in drug development.

The structural attributes of Methyl 6-Amino-5-iodopyridine-3-carboxylate make it an ideal candidate for further functionalization, enabling the synthesis of a wide array of pharmacologically active molecules. The presence of the iodine atom, in particular, facilitates cross-coupling reactions such as Suzuki-Miyaura and Stille couplings, which are pivotal in constructing complex organic frameworks. These reactions are widely employed in the medicinal chemistry community to create novel heterocyclic compounds with potential therapeutic benefits.

In recent years, there has been a surge in research focused on developing treatments for various diseases, including cancer and infectious disorders. Methyl 6-Amino-5-iodopyridine-3-carboxylate has emerged as a crucial building block in the synthesis of targeted therapies. For instance, researchers have leveraged this compound to design small-molecule inhibitors that selectively interact with specific biological pathways dysregulated in diseases like oncology.

One of the most compelling applications of Methyl 6-Amino-5-iodopyridine-3-carboxylate is in the development of radiolabeled probes for positron emission tomography (PET) imaging. The iodine atom can be easily incorporated into radiopharmaceuticals, allowing for non-invasive visualization of biological processes at the molecular level. This has opened new avenues for diagnostic applications, particularly in oncology and neurology, where early detection and precise targeting are critical.

The compound's utility extends beyond diagnostics; it also plays a pivotal role in the synthesis of kinase inhibitors. Kinases are enzymes that play a central role in cell signaling pathways, and their dysregulation is implicated in numerous diseases. By incorporating Methyl 6-Amino-5-iodopyridine-3-carboxylate into drug candidates, chemists can design molecules that selectively inhibit aberrant kinase activity, thereby mitigating disease progression.

Recent advancements in synthetic methodologies have further enhanced the appeal of Methyl 6-Amino-5-iodopyridine-3-carboxylate. Techniques such as flow chemistry and microwave-assisted synthesis have enabled more efficient and scalable production processes. These innovations not only improve yield but also reduce waste, aligning with the growing emphasis on sustainable pharmaceutical practices.

The impact of Methyl 6-Amino-5-iodopyridine-3-carboxylate on drug discovery is underscored by its frequent use in high-throughput screening (HTS) campaigns. HTS allows researchers to rapidly test thousands of compounds for biological activity, expediting the identification of lead candidates. The structural diversity offered by this intermediate has been instrumental in identifying novel therapeutic agents with promising preclinical profiles.

In conclusion, Methyl 6-Amino-5-iodopyridine-3-carboxylate (CAS No. 211308-80-4) represents a cornerstone in modern pharmaceutical synthesis. Its unique structural features and reactivity make it an indispensable tool for medicinal chemists seeking to develop innovative treatments for a myriad of diseases. As research continues to evolve, it is likely that this compound will remain at the forefront of drug discovery efforts, contributing to significant advancements in human health.

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