827616-50-2

Basic information

• Product Name: 3,5-DIIODOPYRIDINE-4-CARBONITRILE
• Synonyms: 3,5-DIIODOPYRIDINE-4-CARBONITRILE;4-Cyano-3,5-diiodopyridine
• CAS NO: 827616-50-2
• Molecular Formula: C6H2I2N2
• Molecular Weight: 355.90242
• Mol File: 827616-50-2.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 398.8 °C at 760 mmHg
• Flash Point: 195 °C
• Appearance: /
• Density: 2.68 g/cm³
• Vapor Pressure: 1.43E-06mmHg at 25°C
• Refractive Index: 1.769
• Sensitive: Light Sensitive
• CAS DataBase Reference: 3,5-DIIODOPYRIDINE-4-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIIODOPYRIDINE-4-CARBONITRILE(827616-50-2)
• EPA Substance Registry System: 3,5-DIIODOPYRIDINE-4-CARBONITRILE(827616-50-2)

Safety Data

• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 827616-50-2(Hazardous Substances Data)

Usage

General Description

3,5-DIIODOPYRIDINE-4-CARBONITRILE is a chemical compound with the molecular formula C6H2I3N3. It is a derivative of pyridine and contains two iodine atoms at positions 3 and 5 on the pyridine ring, as well as a cyano group at position 4. 3,5-DIIODOPYRIDINE-4-CARBONITRILE is commonly used as a building block in organic synthesis and pharmaceutical research. Its unique structure and reactivity make it a valuable intermediate in the production of various organic compounds, including pharmaceutical drugs and agrochemicals. It is also used in the development of new materials and as a reagent in chemical reactions. However, it is important to handle this compound with caution, as it is toxic and may pose health risks if not handled properly.

InChI:InChI=1/C6H2I2N2/c7-5-2-10-3-6(8)4(5)1-9/h2-3H

Upstream product

• 100-48-1 pyridine-4-carbonitrile 

Relevant articles and documents

Direct metalation of heteroaromatic esters and nitriles using a mixed lithium-cadmium base. Subsequent conversion to dipyridopyrimidinones

(Chemical Equation Presented) All pyridine nitriles and esters were metalated at the position next to the directing group using (TMP) 3CdLi in tetrahydrofuran at room temperature. The 2-, 3-, and 4-cyanopyridines were treated with 0.5 equiv of base for 2 h to afford, after subsequent trapping with iodine, the corresponding 3-iodo, 2-iodo, and 3-iodo derivatives, respectively, in yields ranging from 30 to 61%. Cyanopyrazine was similarly functionalized at the 3 position in 43% yield. Ethyl 3-iodopicolinate and -isonicotinate were synthesized from the corresponding pyridine esters in 58 and 65% yield. Less stable ethyl 4-iodonicotinate also formed under the same conditions and was directly converted to ethyl 4-(pyrazol-1-yl)nicotinate in a two-step 38% yield. All three ethyl iodopyridinecarboxylates were involved in a one-pot palladium-catalyzed cross-coupling reaction/cyclization using 2-aminopyridine to afford new dipyrido[1,2-a:3′,2′-d]pyrimidin-11- one, dipyrido[1,2-a:4′,3′-d]pyrimidin-11-one, and dipyrido[1,2-a:3′,4′-d]pyrimidin-5-one in yields ranging from 50 to 62%. A similar crosscoupling/ cyclization sequence was applied to methyl 2-chloronicotinate using 2-aminopyridine, 2-amino-5-methylpyridine, and 1-aminoisoquinoline to give the corresponding tricyclic or tetracyclic compounds in 43-79% yield. Dipyrido[1,2-a:4′,3′-d]pyrimidin-11-one and dipyrido[1,2-a:3′,4′-d]pyrimidin-5-one showed a good bactericidal activity against Pseudomonas aeroginosa. Dipyrido-[1,2-a:2′,3′-d] pyrimidin-5-one and pyrido[2′,3′:4,5]pyrimidino[2,1-a]isoquinolin-8- one showed a fungicidal activity against Fusarium and dipyrido[1,2-a:4′, 3′-d]pyrimidin-11-one against Candida albicans. Ethyl 4-(pyrazol-1-yl) nicotinate and dipyrido[1,2-a:2′,3′-d]pyrimidin-5-one have promising cytotoxic activities, the former toward a liver carcinoma cell line (HEPG2) and the latter toward a human breast carcinoma cell line (MCF7).