Cas no 72299-58-2 ((5-Iodo-pyridin-3-yl)-methanol)

(5-Iodo-pyridin-3-yl)-methanol is a versatile heterocyclic building block featuring a pyridine core substituted with an iodine atom at the 5-position and a hydroxymethyl group at the 3-position. The iodine moiety offers a reactive site for cross-coupling reactions, such as Suzuki or Sonogashira couplings, enabling further functionalization. The hydroxymethyl group provides additional derivatization potential, allowing for esterification, etherification, or oxidation to the corresponding aldehyde. This compound is particularly useful in pharmaceutical and agrochemical research, where it serves as an intermediate in the synthesis of bioactive molecules. Its well-defined reactivity and stability make it a valuable reagent for constructing complex heterocyclic frameworks.
(5-Iodo-pyridin-3-yl)-methanol structure
72299-58-2 structure
Product Name:(5-Iodo-pyridin-3-yl)-methanol
CAS No:72299-58-2
MF:C6H6INO
MW:235.022413730621
MDL:MFCD08457775
CID:549438
PubChem ID:329771436
Update Time:2025-10-19

(5-Iodo-pyridin-3-yl)-methanol Chemical and Physical Properties

Names and Identifiers

    • 3-Pyridinemethanol,5-iodo-
    • (5-Iodo-pyridin-3-yl)-methanol
    • (5-iodopyridin-3-yl)methanol
    • (5-iodanylpyridin-3-yl)methanol
    • (5-iodo-3-pyridinyl)methanol
    • 3-Pyridinemethanol,5-iodo
    • 5-Iodo-3-pyridylcarbinol
    • MFCD08457775
    • SCHEMBL21549405
    • AB45541
    • CS-0206003
    • AKOS015853906
    • (5-iodo-3-pyridyl)methanol
    • 72299-58-2
    • (5-Iodo-pyridin-3-yl)-methanol, AldrichCPR
    • DTXSID90640075
    • FT-0678289
    • A837478
    • (5-Iodopyridin-3-yl)-methanol
    • XCA29958
    • PS-12906
    • DB-029562
    • G81850
    • MDL: MFCD08457775
    • Inchi: 1S/C6H6INO/c7-6-1-5(4-9)2-8-3-6/h1-3,9H,4H2
    • InChI Key: MAESWHLLEUUMGK-UHFFFAOYSA-N
    • SMILES: IC1=CN=CC(=C1)CO

Computed Properties

  • Exact Mass: 234.94900
  • Monoisotopic Mass: 234.94941g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 1
  • Complexity: 89.1
  • 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: 0.6
  • Topological Polar Surface Area: 33.1?2

Experimental Properties

  • Density: 1.982
  • Boiling Point: 333.3°C at 760 mmHg
  • Flash Point: 155.4°C
  • Refractive Index: 1.658
  • PSA: 33.12000
  • LogP: 1.17850

(5-Iodo-pyridin-3-yl)-methanol Security Information

  • Hazardous Material transportation number:NONH for all modes of transport
  • WGK Germany:3
  • Hazard Category Code: 41
  • Safety Instruction: 39
  • Hazardous Material Identification: Xi
  • HazardClass:IRRITANT

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Additional information on (5-Iodo-pyridin-3-yl)-methanol

Recent Advances in the Application of (5-Iodo-pyridin-3-yl)-methanol (CAS: 72299-58-2) in Chemical Biology and Pharmaceutical Research

The compound (5-Iodo-pyridin-3-yl)-methanol (CAS: 72299-58-2) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its versatile applications as a key intermediate in the synthesis of bioactive molecules. This research brief aims to provide an overview of the latest developments involving this compound, focusing on its synthetic utility, biological relevance, and potential therapeutic applications. Recent studies have highlighted its role in the development of novel kinase inhibitors, radiopharmaceuticals, and other small-molecule therapeutics.

One of the most notable applications of (5-Iodo-pyridin-3-yl)-methanol is its use as a building block in the synthesis of kinase inhibitors. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its incorporation into a series of potent and selective inhibitors targeting the PI3K/AKT/mTOR pathway, which is implicated in various cancers. The iodine substituent at the 5-position of the pyridine ring allows for further functionalization via cross-coupling reactions, enabling the rapid diversification of chemical libraries for high-throughput screening.

In addition to its role in kinase inhibitor development, (5-Iodo-pyridin-3-yl)-methanol has shown promise in radiopharmaceutical applications. Researchers at the University of California, San Francisco, recently reported its use as a precursor for the synthesis of iodine-123 and iodine-125 labeled compounds for single-photon emission computed tomography (SPECT) imaging. The presence of the iodine atom makes it an ideal candidate for radiolabeling, and the hydroxymethyl group provides a handle for further conjugation with targeting moieties.

From a synthetic chemistry perspective, recent advances have focused on optimizing the preparation of (5-Iodo-pyridin-3-yl)-methanol to improve yield and scalability. A 2024 publication in Organic Process Research & Development described a novel catalytic system for the direct iodination of 3-pyridinemethanol derivatives, achieving higher regioselectivity and reduced byproduct formation compared to traditional methods. This development is particularly significant for industrial-scale production, where cost-effectiveness and reproducibility are critical considerations.

The compound's potential in drug discovery extends beyond its immediate applications. Computational studies have suggested that derivatives of (5-Iodo-pyridin-3-yl)-methanol may exhibit favorable pharmacokinetic properties, including good blood-brain barrier permeability. This has sparked interest in its use for central nervous system (CNS) drug development, with several pharmaceutical companies reportedly exploring its incorporation into candidates for neurodegenerative diseases.

In conclusion, (5-Iodo-pyridin-3-yl)-methanol (CAS: 72299-58-2) continues to emerge as a valuable scaffold in chemical biology and pharmaceutical research. Its versatility as a synthetic intermediate, combined with recent methodological improvements in its preparation and application, positions it as a compound of significant interest for future drug discovery efforts. Ongoing research is expected to further expand its utility, particularly in the areas of targeted therapeutics and molecular imaging.

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