Description
2-Iodo-4-methylpyridine (CAS No. 22282-60-6) is a high-purity halogenated pyridine derivative with the molecular formula C6H6IN. This organoiodine compound is a valuable intermediate in pharmaceutical and agrochemical synthesis, offering exceptional reactivity for cross-coupling reactions (e.g., Suzuki, Negishi). The methyl group at the 4-position enhances electron density, making it particularly useful for directed metalation and subsequent functionalization. Supplied as crystalline solid with ≥98% purity (HPLC), it is rigorously tested for heavy metals (<10 ppm) and residual solvents. Optimal storage at 2-8°C under inert atmosphere ensures long-term stability. Available in research (1g, 5g) and bulk (25g, 100g) quantities with COA/MSDS documentation.
Properties
- CAS Number: 22282-60-6
- Complexity: 74.9
- IUPAC Name: 2-iodo-4-methyl-pyridine
- InChI: InChI=1S/C6H6IN/c1-5-2-3-8-6(7)4-5/h2-4H,1H3
- InChI Key: DZFWKQYMUZMLSR-UHFFFAOYSA-N
- Exact Mass: 218.95450
- Molecular Formula: C6H6IN
- Molecular Weight: 219.02
- SMILES: CC1=CC(=NC=C1)I
- Topological: 12.9
- Monoisotopic Mass: 218.95450
- Synonyms: 2-Iodo-4-methylpyridine, 22282-60-6, DTXSID40494782, DTXCID40445592, 843-955-6, Pyridine, 2-iodo-4-methyl-, 4-Methyl-2-iodopyridine, MFCD12963767, 2-Iodo-4-picoline, SCHEMBL4008373, XAA28260, AKOS015891955, AS-82640, CS-0436352, D87895, EN300-1666252
Application
2-Iodo-4-methylpyridine serves as a key building block in palladium-catalyzed cross-coupling reactions for drug discovery, particularly in synthesizing kinase inhibitors and antiviral compounds. The iodine moiety enables efficient Sonogashira couplings for alkyne-functionalized heterocycles. In material science, it acts as precursor for N-donor ligands in catalytic systems. The methyl group facilitates C-H activation in late-stage diversification of pharmaceutical intermediates.
Safety and Hazards
GHS Hazard Statements
- H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
- H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]
- H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
- H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
- H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]
- H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
Precautionary Statements
- P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501
Hazard Classes and Categories
- Acute Tox. 4 (100%)
- Acute Tox. 4 (100%)
- Skin Irrit. 2 (100%)
- Eye Irrit. 2A (100%)
- Acute Tox. 4 (100%)
- STOT SE 3 (100%)
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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.


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