62674-71-9

Basic information

• Product Name: 2-Iodo-6-methylpyridine
• Synonyms: 2-Iodo-6-methylpyridine;6-Iodo-2-picoline;Pyridine,2-iodo-6-methyl-
• CAS NO: 62674-71-9
• Molecular Formula: C₆H₆IN
• Molecular Weight: 219.02
• EINECS: 214-589-6
• Mol File: 62674-71-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 222.12 °C at 760 mmHg
• Flash Point: 88.135 °C
• Appearance: /
• Density: 1.81 g/cm³
• Vapor Pressure: 0.154mmHg at 25°C
• Refractive Index: 1.612
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 2.57±0.10(Predicted)
• CAS DataBase Reference: 2-Iodo-6-methylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Iodo-6-methylpyridine(62674-71-9)
• EPA Substance Registry System: 2-Iodo-6-methylpyridine(62674-71-9)

Safety Data

• Hazardous Substances Data: 62674-71-9(Hazardous Substances Data)

Usage

General Description

2-Iodo-6-methylpyridine is a specialized chemical compound with a molecular formula of C6H6IN. It is classified as an organic compound with elements of iodine, carbon, hydrogen, and nitrogen. The compound is part of the halopyridines group, which are pyridines in which the hydrogen is replaced by a halogen. 2-Iodo-6-methylpyridine is often used in the research and development phase in labs, particularly in the field of medicinal chemistry and it has crucial applications in the synthesis of various pharmaceutical intermediates. It must be handled with care due to its potential hazards.

InChI:InChI=1/C6H6IN/c1-5-3-2-4-6(7)8-5/h2-4H,1H3

Upstream product

• 109-06-8 α-picoline 
• 18368-63-3 6-chloro-2-picoline 
• 5315-25-3 2-bromo-6-methylpyridine 
• 75-36-5 acetyl chloride 
• 1161941-06-5 6-methylpyridin-2-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate 
• 154447-04-8 6-methyl-2-(trifluoromethanesulfonyl)oxypyridine 

Downstream Products

• 1007351-80-5 C₂₉H₃₂N₂O₄ 
• 1007351-68-9 C₂₈H₃₀N₂O₃ 
• 1007351-45-2 C₂₈H₃₀N₂O₂ 
• 1007351-24-7 C₂₇H₂₈N₂O₂ 
• 1824-81-3 2-Amino-6-methylpyridine 
• 656800-40-7 trimethyl-[2-(6-methyl-2-pyridyl)ethynyl]silane 
• 30413-58-2 2-ethynyl-6-methylpyridine 
• 1448017-14-8 6-methyl-2-[2-(6-methylpyridin-2-yl)-6-vinylphenyl]pyridine 

Relevant articles and documents

The preparation of the α-iodo-substituted tripods within the series of tris(2-pyridylmethyl)amine ligands, and the characterization of the corresponding I1-3TPAFeCl2 complexes

We report in this communication the easy preparation of the α-iodo substituted tripods within the series of tris(2-pyridylmethyl)amine ligands, I1TPA, I2TPA and I3TPA, respectively. The characterization of the corresponding FeCl2 complexes in solution is described and structural analysis by X-ray diffraction for I 1TPAFeCl2 and I2TPAFeCl2 is also reported. The steric effect of the iodo substituent is evidenced: (i) by elongation of the metal to iodo-pyridine distance within I 1TPAFeCl2, which however remains a very stable compound; (ii) by decoordination of one substituted pyridine in I2TPAFeCl 2 and I3TPAFeCl3. In I2TPAFeCl 2 and in the solid state, this uncoordinated pyridine strongly interacts with the same fragment of the neighbouring molecule, providing an overall dinuclear arrangement for this complex.

Microwave-assisted trans-halogenation reactions of various chloro-, bromo-, trifluoromethanesulfonyloxy- and nonafluorobutanesulfonyloxy-substituted quinolines, isoquinolines, and pyridines leading to the corresponding iodinated heterocycles

(Chemical Equation Presented) Microwave irradiation of certain chloro-, bromo-, trifluoromethanesulfonyloxy- and nonafluorobutanesulfonyloxy-substituted quinolines in the presence of acetic anhydride and sodium iodide leads, via a trans-halogenation process, to the corresponding iodides in high yield. Related conversions involving pyridines and isoquinolines can also be achieved under similar conditions.

Silyl-mediated halogen/halogen displacement in pyridines and other heterocycles

Heating with bromotrimethylsilane converts 2-chloropyridine into 2-bromopyridine and 2-chloro-6-methylpyridine into 2-bromo-6-methylpyridine. Both 2-chloropyridines and 2-bromopyridines give the corresponding iodo compound when treated with in situ generated iodotrimethylsilane. Although 3- and 4-chloropyridine are completely inert, 2,4-dichloropyridine undergoes the halogen/halogen exchange simultaneously at the 2- and 4-position. Halogen displacement takes place exclusively at the 2-position with 2,3-dichloropyridine and 2,5-dichloropyridine. In agreement with the intermediacy of N-trimethylsilylpyridinium salts as a prerequisite for the occurrence of halogen exchange, neither 2-fluoropyridine and 2-fluoro-6-methylpyridine nor any 2,6-dihalopyridine reacts. Finally, bromine/chlorine and iodine/chlorine substitution can also be accomplished with 2-or 4-chloroquinoline, 1-chloroisoquinoline, 2-chloropyrimidine, chloropyrazine and 2,3-dichloroquinoxaline as substrates. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002).