Nitriles used to be known as cyanides; the smallest organic nitrile is ethanenitrile, CH3CN, (old name: methyl cyanide or acetonitrile – and sometimes now called ethanonitrile). 105-34-0, formula is C4H5NO2, Name is Methyl 2-cyanoacetate. Nitriles are found in many useful compounds, including methyl cyanoacrylate, used in super glue, and nitrile rubber, a nitrile-containing polymer used in latex-free laboratory and medical gloves. Computed Properties of 105-34-0.
Blocka, Aleksandra;Chaladaj, Wojciech research published 《 Tandem Pd-Catalyzed Cyclization/Coupling of Non-Terminal Acetylenic Activated Methylenes with (Hetero)Aryl Bromides》, the research content is summarized as follows. A new method for a tandem Pd-catalyzed intramol. addition of active methylene compounds to internal alkynes ZCH(X)(CH2)3CCR (R = Me, Et, Ph; X = COOMe, CN, C(O)Me, COOi-Pr, SO2Me; Y = COOMe, C(O)Me, C(O)i-Pr, SO2Ph, COOEt) followed by coupling with aryl and heteroaryl bromides R1Br (R1 = Ph, thiophen-2-yl, benzodioxol-5-yl, etc.) was reported. Highly substituted vinylidenecyclopentanes (E)-I were obtained with good yields, complete selectivity, and excellent functional group tolerance. A plausible mechanism, supported by DFT calculations, involves the oxidative addition of bromoarene to Pd(0), followed by cyclization and reductive elimination. The excellent regio- and stereoselectivity arises from the 5-exo-dig intramol. addition of the enol form of the substrate to alkyne activated by the Π-acidic Pd(II) center, postulated as the rate-determining step.
105-34-0, Methyl cyanoacetate is an alkyl cyanoacetate ester.
Methyl cyanoacetate is the intermediate product in pharmaceutical organic synthesis as well as in the synthesis of some biologically active compounds used in agriculture. It undergoes calcite or fluorite catalyzed Knövenagel condensation with aromatic aldehydes, giving the corresponding arylidenemalononitriles and (E)-α -cyanocinnamic esters.
Methyl Cyanoacetate is often used as a nucleophile in the electrochemical oxidation of catechols. Methyl Cyanoacetate is also a reagent in the synthesis of Methyl 2-Amino-4-trifluoromethylthiophene-3-carboxylate (M287290); a compound used in the synthesis of DPP-IV inhibitors for treating type 2 diabetes., Computed Properties of 105-34-0
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts