99071-55-3

Usage

Uses

Used in Pharmaceutical Industry:
2-[4-(Cyanomethyl)phenyl]acetamide is used as an intermediate in the production of pharmaceuticals for its potential role in the synthesis of various medicinal compounds.
Used in Organic Compounds Production:
2-[4-(Cyanomethyl)phenyl]acetamide is used as an intermediate in the production of other organic compounds, leveraging its unique structure and properties for the creation of specialty chemicals.
Used in Medicinal Chemistry Research:
2-[4-(Cyanomethyl)phenyl]acetamide is utilized in medicinal chemistry research for its biological activity, which may contribute to the development of new therapeutic agents or drug candidates.

InChI:InChI=1/C10H10N2O/c11-6-5-8-1-3-9(4-2-8)7-10(12)13/h1-4H,5,7H2,(H2,12,13)

Upstream product

• 622-75-3 1,4-phenylenediacetonitrile 

Relevant academic research and scientific papers

Hemilability-Driven Water Activation: A NiII Catalyst for Base-Free Hydration of Nitriles to Amides

The NiII complex 1 containing pyridyl- and hydroxy-functionalized N-heterocyclic carbenes (NHCs) is synthesized and its catalytic utility for the selective nitrile hydration to the corresponding amide under base-free conditions is evaluated. The title compound exploits a hemilabile pyridyl unit to interact with a catalytically relevant water molecule through hydrogen-bonding and promotes a nucleophilic water attack to the nitrile. A wide variety of nitriles is hydrated to the corresponding amides including the pharmaceutical drugs rufinamide, Rifater, and piracetam. Synthetically challenging α-hydroxyamides are accessed from cyanohydrins under neutral conditions. Related catalysts that lack the pyridyl unit (i.e., compounds 2 and 4) are not active whereas those containing both the pyridyl and the hydroxy or only the pyridyl pendant (i.e., compounds 1 and 3) show substantial activity. The linkage isomer 1′ where the hydroxy group is bound to the metal instead of the pyridyl group was isolated under different crystallization conditions insinuating a ligand hemilabile behavior. Additional pKa measurements reveal an accessible pyridyl unit under the catalytic conditions. Kinetic studies support a ligand-promoted nucleophilic water addition to a metal-bound nitrile group. This work reports a Ni-based catalyst that exhibits functional hemilability for hydration chemistry.

Bifunctional water activation for catalytic hydration of organonitriles

Treatment of [Rh(COD)(μ-Cl)]2 with excess tBuOK and subsequent addition of 2 equiv of PIN?HBr in THF afforded [Rh(COD)(κC2-PIN)Br] (1) (PIN = 1-isopropyl-3-(5,7-dimethyl-1, 8-naphthyrid-2-yl)imidazol-2-ylidene, COD = 1,5-cyclooctadiene). The X-ray structure of 1 confirms ligand coordination to "Rh(COD)Br" through the carbene carbon featuring an unbound naphthyridine. Compound 1 is shown to be an excellent catalyst for the hydration of a wide variety of organonitriles at ambient temperature, providing the corresponding organoamides. In general, smaller substrates gave higher yields compared with sterically bulky nitriles. A turnover frequency of 20 000 h-1 was achieved for the acrylonitrile. A similar Rh(I) catalyst without the naphthyridine appendage turned out to be inactive. DFT studies are undertaken to gain insight on the hydration mechanism. A 1:1 catalyst-water adduct was identified, which indicates that the naphthyridine group steers the catalytically relevant water molecule to the active metal site via double hydrogen-bonding interactions, providing significant entropic advantage to the hydration process. The calculated transition state (TS) reveals multicomponent cooperativity involving proton movement from the water to the naphthyridine nitrogen and a complementary interaction between the hydroxide and the nitrile carbon. Bifunctional water activation and cooperative proton migration are recognized as the key steps in the catalytic cycle.