827616-50-2

Usage

Uses

Used in Organic Synthesis:
3,5-DIIODOPYRIDINE-4-CARBONITRILE is used as a building block in organic synthesis for its unique reactivity and structural properties, enabling the production of a wide range of organic compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 3,5-DIIODOPYRIDINE-4-CARBONITRILE is utilized as an intermediate in the development of pharmaceutical drugs, contributing to the creation of novel therapeutic agents.
Used in Agrochemicals Production:
3,5-DIIODOPYRIDINE-4-CARBONITRILE is employed as a key intermediate in the synthesis of agrochemicals, playing a crucial role in the development of new pesticides and other agricultural chemicals.
Used in Material Science:
3,5-DIIODOPYRIDINE-4-CARBONITRILE is also used in the development of new materials, where its unique properties can be leveraged to create innovative substances with specific applications.
Used as a Reagent in Chemical Reactions:
3,5-DIIODOPYRIDINE-4-CARBONITRILE serves as a reagent in various chemical reactions, facilitating specific transformations and syntheses that are otherwise challenging to achieve.

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 academic research and scientific papers

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).

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.