22282-58-2

Basic information

• Product Name: 2-Iodo-3-methylpyridine
• Synonyms: 2-IODO-3-METHYLPYRIDINE;2-Iodo-3-picoline;2-IODO-3-METHYLPYRIDINE 97%
• CAS NO: 22282-58-2
• Molecular Formula: C₆H₆IN
• Molecular Weight: 219.02
• EINECS: -0
• Product Categories: Halides;Pyridines;pyridine;Heterocycle-Pyridine series
• Mol File: 22282-58-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 80°C/0.3mm
• Flash Point: >110℃
• Appearance: /
• Density: 1.827 g/mL at 25 °C
• Vapor Pressure: 0.069mmHg at 25°C
• Refractive Index: 1.625
• Storage Temp.: 2-8°C
• PKA: 2.14±0.10(Predicted)
• Sensitive: Light Sensitive
• BRN: 5328169
• CAS DataBase Reference: 2-Iodo-3-methylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Iodo-3-methylpyridine(22282-58-2)
• EPA Substance Registry System: 2-Iodo-3-methylpyridine(22282-58-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38-41-37/38-22
• Safety Statements: 26-36/37/39-39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 22282-58-2(Hazardous Substances Data)

Usage

General Description

2-Iodo-3-methylpyridine, also known as 3-Iodo-2-methylpyridine, is a chemical compound with the molecular formula C6H6IN. It is a halogen-substituted derivative of pyridine, which is a heterocyclic aromatic compound. This chemical is commonly used as a building block in organic synthesis and pharmaceutical research due to its reactivity and potential for introducing the iodo group into various organic molecules. It is also used in the production of agrochemicals and as an intermediate in the synthesis of other chemical compounds. However, it is important to handle this compound with care, as it is toxic and can be harmful if ingested, inhaled, or comes into contact with skin.

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

Upstream product

• 154447-02-6 3-methylpyridin-2-yl trifluoromethanesulfonate 
• 3430-17-9 2-bromo-3-picoline 

Downstream Products

• 1466564-54-4 C₂₆H₂₀ClN₅O₂ 
• 1466564-57-7 C₃₂H₂₆N₆O₃ 
• 1466565-03-6 C₃₀H₂₈N₆O₃ 
• 1258786-30-9 3-methyl-2-(toluene-4-sulfonyl)-pyridine 
• 30413-59-3 2-ethynyl-3-methylpyridine 

Relevant articles and documents

Homoleptic zincate-promoted room-temperature halogen-metal exchange of bromopyridines

Homoleptic lithium tri- and tetraalkyl zincates were reacted with a set of bromopyridines. Efficient and chemoselective bromine-metal exchanges were realized at room temperature with a substoichiometric amount of nBu 4ZnLi2·TMEDA reagent (1/3 equiv; TMEDA=N,N,N′,N′-tetramethylethylenediamine). This reactivity contrasted with that of tBu4ZnLi2·TMEDA, which was inefficient below one equivalent. DFT calculations allowed us to rationalize the formation of N...Li stabilized polypyridyl zincates in the reaction. The one-pot difunctionalization of dibromopyridines was also realized using the reagent stoichiometrically. The direct creation of C-Zn bonds in bromopyridines enabled us to perform efficient Negishi-type cross-couplings. Mild zincation! nBu4ZnLi2·TMEDA (in substoichiometric amounts) promoted efficient and chemoselective room-temperature bromine-metal exchange of a range of bromopyridines (see scheme). DFT calculations strongly supported the formation of a stabilized tripyridylzincate, which could be reacted with electrophiles or be directly involved in palladium-catalyzed cross-coupling reactions.

One-pot iodination of hydroxypyridines

(Chemical Equation Presented) A one-pot, high-yielding iodination of hydroxypyridines and hydroxyquinolines is described. The iodination proceeds under mild conditions, and the products are obtained in high yield without the need for chromatographic purif