2909-14-0

Usage

Uses

Used in Pharmaceutical Industry:
Ethanimidamide, N,N-dimethylis used as a solvent for the synthesis of pharmaceutical compounds due to its ability to dissolve a wide range of substances, facilitating the manufacturing process and improving the efficiency of drug production.
Used in Polymer Industry:
In the polymer industry, Ethanimidamide, N,N-dimethylis utilized as a solvent for the production of polymers. Its capacity to dissolve various materials allows for the creation of a diverse array of polymers with specific properties tailored to different applications.
Used in Electronics Industry:
Ethanimidamide, N,N-dimethylis employed as a solvent in the electronics industry for the manufacturing of electronic components. Its solubility properties are advantageous in the production process, ensuring the quality and performance of electronic devices.
Used in Other Industries:
Ethanimidamide, N,N-dimethylis also used in various other industries for applications such as a carrier fluid in electroplating processes, a cleaning agent for delicate equipment, and a component in the formulation of certain types of paints and coatings. Its versatility as a solvent makes it a valuable asset in these fields.

Upstream product

• 60316-21-4 N,N-Dimethyl-N'-(α-methyl-β-carbethoxyvinyl)acetamidin 
• 18871-66-4 N,N-dimethylacetamide dimethyl acetal 
• 79-06-1 2-propenamide 
• 260783-66-2 [Cp*Ir(η3-CH2CHCHPh)(NH=C(NMe2)Me)]OTf 
• 603-35-0 triphenylphosphine 
• 124-40-3 dimethyl amine 
• 75-05-8 acetonitrile 

Downstream Products

• 4023-12-5 N¹,N¹-Dimethyl-N²-(phenyl)acetamidin 
• 56776-17-1 C₁₀H₁₃N₅O₆ 

Relevant academic research and scientific papers

Activation of acetonitrile in [Cp*Ir(η3-CH2CHCHPh)(NCMe)]+: Crystal structures of iridium-amidine, imino-ether, amido, and amide complexes

Reactions of [Cp*Ir(η3-CH2CHCHPh)(NCMe)]OTf (1) with protic amines, alcohols, and water produce amidine complexes [Cp*Ir(η3-CH2CHCHPh)(NH=C(NR2)Me)]OTf (2) (R2 = (Me)2 (a), (Me)(H) (b), (i-Pr)(H) (c), (-CH2(CH2)3CH2-) (d)), imino-ether complexes [Cp*Ir-(η3-CH2CHCHPh)(NH=C(OR′)Me)]OTf (4) (R′ = Me (a), Et (b), i-Pr (c)), and amido complex Cp*Ir(η3-CH2CHCHPh)(NHC(=O)Me) (5-K), respectively. The keto form amido complex 5-K undergoes tautomerization to give the enol form complex Cp*Ir(η3-CH2CHCHPh)(N= C(OH)Me) (5-E) in polar solvents. Tertiary amines (NMe3, NEt3) react with 1 in chlorinated solvents (XCl) to give the chloro complex Cp*IrCl(η3-CH2CHCHPh) (3) and quaternary ammonium salts [R3NX]OTf(R = Me, Et and X = CH2Cl, CH3, CHCl2, CCl3, PhCH2). Crystal structures of 2a, 4a, 5-K, and [Cp*Ir(NH=C(OH)Me)(OH2)(PPh3)]OTf2 (6) have been determined by single-crystal X-ray diffraction analysis, which lead us to suggest hybrid structures, Ir--NH-C(=N+Me2)Me (2a′) for 2a and Ir--NH-C(=O+Me)Me (4a′) for 4a to some extent. Complexes 2 and 4 react with PPh3 to give an iridium(III) complex [Cp*Ir(η3-CH2CHCHPh)(PPh3)]OTf (7) and the free amidines NH=C(NR2)Me (8) and imino-ethers NH=C(OR′)Me (9), respectively. Nitrile complexes 1 and [Cp*Ir(η3-CH2CHCHPh)(NCCH= CHMe)]OTf(10) catalyze the hydration of the nitriles in the presence of Na2CO3 to produce amides, and the benzonitrile complex [Cp*Ir(η3-CH2CHCHPh)(NCPh)]OTf(11) catalyzes the methanolysis of benzonitrile in the presence of Na2CO3 to produce NH=C(OMe)Ph. Plausible mechanisms for these catalytic reactions are suggested with the amido and imino-ether complexes such as 4 and 5 being involved.

Stimuli-responsive polymer utilizing keto-enol tautomerization

A stimuli-responsive polymer derivative utilizing keto-enol tautomerization. Also disclosed are a simple process for producing an N-acyl(meth)acrylamide derivative which can be used as a monomer for the stimuli-responsive polymer, a process for the production of an intermediate thereof, and an intermediate thus produced.

Copper(I)-induced addition of amines to unactivated nitriles: The first general one-step synthesis of alkyl amidines

Cu(I)Cl promotes the condensation of acetonitrile 1a and benzonitrile 1b with primary and secondary amines 2a-g into amidines 3a-j under mild conditions, in high to quantitative yields. Stoichiometric formation of Cu(I)-amidines complexes allows to control the degree of substitution of resulting amidines.

Use of Lanthanide(III) Ions as Catalysts for the Reactions of Amines with Nitriles

Catalytic amounts of lanthanide(III) triflates promote reactions between amines and nitriles leading to a variety of products.The Ln3+ ions activate weakly coordinating nitriles at large amine: Ln3+ mole ratios, even in the presence of amines that form thermodynamically stable complexes with Ln3+ ions.The reactions involving primary monoamines and diamines appear to be general and provide a viable synthetic route to N,N'-disubstituted amidines (2) and cyclic amidines (4), respectively.Symmetrically substituted triazines (8 or 9) are observed as byproducts in some of these systems when the reactions are carried out by using excess nitrile.Secondary alicyclic amines or dimethylamine reacts with acetonitrile to yield pyrimidines (6) and 2,4,6-trimethyl-s-triazine (8).Two routes to triazine have been proposed, one involving the reaction of ammonia with the nitrile and the second involving the reaction of an amidine (1 or 5) with the nitrile.The ability of Ln3+ ions to activate nitriles under conditions that oppose nitrile coordination is attributed to the lability of Ln3+ complexes derived from N-donors.