2918-67-4

Usage

Uses

Used in Adhesives Industry:
N-Cyclohexyl methacrylamide is used as a component in the formulation of adhesives for enhancing their strength and durability.
Used in Coatings Industry:
In the coatings industry, N-Cyclohexyl methacrylamide is utilized as a key ingredient in the production of coatings that offer improved performance and longevity.
Used in Sealants Industry:
N-Cyclohexyl methacrylamide is employed as a constituent in sealant formulations to improve their sealing properties and resistance to environmental factors.
Used in Specialty Chemicals Production:
This chemical compound is also used in the synthesis and production of specialty chemicals, contributing to the development of unique and high-performance products.
Used in Pharmaceuticals:
N-Cyclohexyl methacrylamide finds application in the pharmaceutical sector, where it is utilized in the development of various drug formulations and delivery systems.

InChI:InChI=1/C10H17NO/c1-8(2)10(12)11-9-6-4-3-5-7-9/h9H,1,3-7H2,2H3,(H,11,12)

Upstream product

• 463-49-0 1,2-propanediene 
• 201230-82-2 carbon monoxide 
• 108-91-8 cyclohexylamine 
• 79-41-4 poly(methacrylic acid) 
• 110228-40-5 2-bromo-2-methyl-N-cyclohexylpropanamide 
• 108-94-1 cyclohexanone 
• 920-46-7 Methacryloyl chloride 
• 21043-40-3 1-cyclopentylpiperazine 

Downstream Products

• 1309763-11-8 1-cyclohexyl-3-methyl-5,6-diphenylpyridin-2(1H)-one 
• 1326317-57-0 potassium N-cyclohexyl-2-methyl-3-(trifluoroborato)propanamide 
• 1414882-47-5 (2E,4Z)-n-butyl 6-cyclohexylamino-5-methyl-6-oxohexa-2,4-dienoate 
• 1450754-09-2 (Z)-N-[3-(cyclohexylamino)-2-methyl-3-oxoprop-1-enyl]-4-nitrobenzamide 

Relevant academic research and scientific papers

Effect of Transition Metals on Chemodivergent Cross-Coupling of Acrylamides with Vinyl Acetate via C-H Activation

A novel chemodivergent cross-coupling of acrylamides and vinyl acetates has been realized via metal-catalyzed vinylic C-H activation. The selective olefinic C-H vinylation and alkenylation reaction was examined with a variety of differently functionalized acrylamides. The reaction efficiently generates a range of highly synthetically valuable butadienes with good functional group tolerance in good to moderate yields. A possible catalytic reaction mechanism involving the chelation-assisted olefinic C-H activation via an acetate-assisted deprotonation pathway is proposed.

Favorskii-like rearrangement of an aliphatic α-halo amide

The reaction of the α-bromoamide 2a with 1-cyclopentylpiperazine gives the Favorskii-like rearranged product 4 when the reaction is heated to 70 °C in a mixture of aqueous potassium hydroxide and ethanol. However, when solid sodium carbonate/potassium iodide is used in ethanol, the nonrearranged product 3a is formed instead. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

Ir(III)-catalyzed mild C-H amidation of arenes and alkenes: An efficient usage of acyl azides as the nitrogen source

Reported herein is the development of the Ir(III)-catalyzed direct C-H amidation of arenes and alkenes using acyl azides as the nitrogen source. This procedure utilizes an in situ generated cationic half-sandwich iridium complex as a catalyst. The reaction takes place under very mild conditions, and a broad range of sp2 C-H bonds of chelate group-containing arenes and olefins are smoothly amidated with acyl azides without the intervention of the Curtius rearrangement. Significantly, a wide range of reactants of aryl-, aliphatic-, and olefinic acyl azides were all efficiently amidated with high functional group tolerance. Using the developed approach, Z-enamides were readily accessed with a complete control of regio- and stereoselectivity. The developed direct amidation proceeds in the absence of external oxidants and releases molecular nitrogen as a single byproduct, thus offering an environmentally benign process with wide potential applications in organic synthesis and medicinal chemistry.

Ruthenium- and rhodium-catalyzed cross-coupling reaction of acrylamides with alkenes: Efficient access to (Z,E)-dienamides

Ruthenium- and rhodium-catalyzed direct oxidative cross-coupling reactions of acrylamides with alkenes were developed. These methods provide an efficient route for the synthesis of (Z,E)-dienamides in excellent yields with good stereoselectivity. The catalytic systems allowed oxidative olefination of a wide range of alkenes bearing different functional groups, such as CO2R, COMe, SO2Ph, aryl, CONHBn, CN, PO(OEt)2, as well as Weinreb amide.

Copper-catalyzed β-boration of α,β-unsaturated carbonyl compounds with tetrahydroxydiborane

The copper-catalyzed β-boration of α,β-unsaturated carbonyl compounds with tetrahydroxydiborane has been developed. This diboron reagent allows direct, efficient access to boronic acids and their derivatives. Primary, secondary, and tertiary α,β-unsaturated amides are converted to the corresponding β-trifluoroboratoamides in good to excellent yields. The β-boration of a variety of α,β-unsaturated esters and ketones is also reported.

Alkylation of Rink's amide linker on polystyrene resin: A reductive amination approach to modified amine-linkers for the solid phase synthesis of N-substituted amide derivatives

Reductive amination of aldehydes and ketones using sodium cyanoborohydride and Rink's 4-(2',4'-dimethoxyphenyl-aminomethyl)-phenoxymethyl-linked polystyrene resin [Rink's amine linker on copoly-(styrene-1%-divinylbenzene)]1 2 affords high yields of linker-bound, N-alkyl amines with excellent chemical selectivity. Subsequent coupling with acid derivatives gave derivatized N-substituted amides in excellent yields after cleavage from the solid-support.

The phosphazo route to 2-alkenamides from acrylic acid and its derivatives

2-Alkenamides are formed in good isolated yields (generally up to 70%) by the reaction of in situ-generated phosphazo compounds issued from aliphatic, alicyclic and aromatic primary amines, with acrylic acid and its derivatives.

Electrochemistry of 2-Bromo-2-methylpropanamides. Reduction Mechanism and Cyclocoupling Reaction with Amide Solvents

The electrochemical reduction of series of secondary and tertiary α-bromoisobutyramides has been studied in dipolar aprotic solvents.A carbanion is formed at the mercury electrode as a consequence of two-electron C-Br bond cleavage.Voltammetry and macroelectrolysis point to a self-protonation mechanism, the carbanion undergoing protonation by a parent molecule to yield the isobutyramide.Concurrently, tertiary 2-bromoamides undergo 1,2-elimination to yield an αβ-unsaturated amide, while secondary 2-bromoamides are deprotonated at the nitrogen atom, affording a bromo-containing anion.The decay of the latter is strongly dependent on the solvent and the substituent at nitrogen.In acetonitrile, elimination and fragmentation products are identified in the electrolysed solution.On the other hand, in N,N-dimethylformamide or N,N-dimethylacetamide, the bromo-containing anion is eventually cyclocondensed onto the carbonyl group of the amide solvent, to yield an oxazolidin-4-one derivative.Preliminary data suggest that an analogous cyclocoupling reaction takes place when the reduction is carried out in 1-methyl-2-pyrrolidone.