827616-52-4

Basic information

• Product Name: 3-IODOPYRIDINE-2-CARBONITRILE
• Synonyms: 3-IODOPYRIDINE-2-CARBONITRILE;2-Cyano-3-iodopyridine;3-iodopicolinonitrile;2-Pyridinecarbonitrile,3-iodo-
• CAS NO: 827616-52-4
• Molecular Formula: C6H3IN2
• Molecular Weight: 230.00589
• Product Categories: Pyridines;Heterocycle-Pyridine series
• Mol File: 827616-52-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 98-100℃
• Boiling Point: 330.744 °C at 760 mmHg
• Flash Point: 153.828 °C
• Appearance: /
• Density: 2.043 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.67
• Storage Temp.: 2-8°C(protect from light)
• Sensitive: Light Sensitive
• CAS DataBase Reference: 3-IODOPYRIDINE-2-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-IODOPYRIDINE-2-CARBONITRILE(827616-52-4)
• EPA Substance Registry System: 3-IODOPYRIDINE-2-CARBONITRILE(827616-52-4)

Safety Data

• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 827616-52-4(Hazardous Substances Data)

Usage

Uses

Used to prepare Grignard reagents which are widely used in organic synthesis.2-Cyano-3-iodopyridine are used in coupling reactions. Has wide application in the pharmaceutical as well as chemical industries.

InChI:InChI=1/C6H3IN2/c7-5-2-1-3-9-6(5)4-8/h1-3H

Upstream product

• 100-70-9 2-Cyanopyridine 

Relevant articles and documents

New in situ trapping metalations of functionalized arenes and heteroarenes with TMPLi in the presence of ZnCl2 and other metal salts

The addition of TMPLi to a mixture of an aromatic or heteroaromatic substrate with a metal salt such as MgCl2, ZnCl2, or CuCN at -78 °C first leads to lithiation of the arene followed by transmetalation with the metal salt to afford functionalized organometallic compounds of Mg, Zn, or Cu. This in situ trapping method allows an expedited metalation (-78 °C, 5 min) of a range of sensitive pyridines (bearing a nitro, ester, or cyano group) and allows the preparation of kinetic regioisomers of functionalized aromatic compounds or heterocycles not otherwise available by standard metalating agents, such as TMPMgCl·LiCl or TMPZnCl·LiCl. Fast, faster, the fastest: Aromatic and heterocyclic substrates, when treated with TMPLi (TMP=2,2,6,6-tetramethylpiperidyl), undergo a kinetic lithiation and then a transmetalation with a metal salt such as MgCl2, ZnCl 2, or CuCN. This allows an expedited metalation of sensitive pyridines bearing a nitro, ester, or cyano group and allows the preparation of kinetic regioisomers of functionalized aromatic compounds or heterocycles.

Synthesis of ortho-substituted cyanopyridines through lithio intermediate trapping

Ortholithiation of 4-cyanopyridine using 2,2,6,6-tetramethylpiperidide (LiTMP) and trapping the lithio intermediate with electrophiles represents an efficient and straightforward access to ortho-substituted-4-cyanopyridines. The cyano group can be used as an ortho-directing group and allows the preparation of 3-halogeno-4-cyanopyridines. Reactivity of 2- and 3-cyanopyridines is also investigated and seems to give similar results.