2719-26-8

Basic information

• Product Name: Cyclohexanecarboxamide, N-phenyl-
• Synonyms: Cyclohexanecarboxamide, N-phenyl-
• CAS NO: 2719-26-8
• Molecular Formula: C₁₃H₁₇NO
• Molecular Weight: 203.28
• Mol File: 2719-26-8.mol

Chemical Properties

• Boiling Point: 387.3°Cat760mmHg
• Flash Point: 232.2°C
• Appearance: /
• Density: 1.098g/cm³
• Vapor Pressure: 3.32E-06mmHg at 25°C
• Refractive Index: 1.578
• CAS DataBase Reference: Cyclohexanecarboxamide, N-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanecarboxamide, N-phenyl-(2719-26-8)
• EPA Substance Registry System: Cyclohexanecarboxamide, N-phenyl-(2719-26-8)

Safety Data

• Hazardous Substances Data: 2719-26-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Cyclohexanecarboxamide, N-phenylis used as an intermediate in the production of various pharmaceuticals for its ability to be incorporated into the molecular structure of different drugs, enhancing their therapeutic properties and effectiveness.
Used in Agrochemical Industry:
In the agrochemical industry, Cyclohexanecarboxamide, N-phenylis utilized as an intermediate in the synthesis of various agrochemicals, contributing to the development of more effective and targeted pest control solutions.
Used in Organic Synthesis:
Cyclohexanecarboxamide, N-phenylserves as a building block in the synthesis of other organic compounds, enabling the creation of a wide range of chemical products with diverse applications.
Used in Chemical Research:
Cyclohexanecarboxamide, N-phenylis also used in the field of chemical research, where it aids in the exploration of new chemical reactions, mechanisms, and the development of innovative synthetic methods.

InChI:InChI=1/C13H17NO/c15-13(11-7-3-1-4-8-11)14-12-9-5-2-6-10-12/h2,5-6,9-11H,1,3-4,7-8H2,(H,14,15)

Upstream product

• 62-53-3 aniline 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 2043-61-0 cyclohexanecarbaldehyde 
• 98-89-5 Cyclohexanecarboxylic acid 
• 4904-55-6 cyclohexanecarbonyl peroxide 
• 538-75-0 dicyclohexyl-carbodiimide 
• 3743-70-2 N-(2-hydroxyphenyl)benzamide 
• 110-83-8 cyclohexene 
• 473440-42-5 cyclohexylcarbonyl 2-(5,5-dimethyl-2-thiono-1,3,2-dioxaphosphorinanyl)sulfide 
• 100-09-4 4-methoxybenzoic acid 
• 60014-85-9 (1,1-dibromomethylene)cyclohexane 
• 701-73-5 methyl N-phenyldithiocarbamate 
• 22651-87-2 cyclohexanecarboxylic acid anhydride 
• 100-49-2 cyclohexylmethyl alcohol 

Downstream Products

• 101090-33-9 2-cyclohexyLiDene-3-phenyl-oxazolidine-4,5-dione 
• 6064-01-3 Cyclohexanecarbonyl-phenyl-carbamic acid isopropyl ester 
• 1360571-16-9 2,4-dichlorophenyl N-phenylcyclohexanecarboximidate 
• 91790-88-4 C₁₉H₂₂N₂ 
• 53300-46-2 N-(cyclohexylthiocarbonyl)aniline 
• 128815-38-3 N,N-diphenylcyclohexanecarboxamide 
• 315712-37-9 N-(4-bromophenyl)-cyclohexanecarboxamide 
• 315712-26-6 N-(4-methoxyphenyl)-cyclohexanecarboxamide 
• 220383-46-0 N-(2-trifluoromethylphenyl)cyclohexanecarboxamide 
• 548763-46-8 N-(4-hydroxyphenyl)cyclohexanecarboxamide 
• 126541-71-7 N-cyclohexylmethyl-aniline; hydrochloride 
• 200706-63-4 N-(4-iodophenyl)cyclohexanecarboxamide 

Relevant articles and documents

Copper-Catalyzed Carbonylative Coupling of Cycloalkanes and Amides

Carbonylation reactions are a most powerful method for the synthesis of carbonyl-containing compounds. However, most known carbonylation procedures still require noble-metal catalysts and the use of activated compounds and good nucleophiles as substrates.

Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides

Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.

Preparation method of amide

The invention relates to a preparation method of an amide, wherein, under the action of oxygen, the isothiocyanate and the aldehyde can react to form an amide, and the reaction temperature can be effectively increased only when not less than 110 °C. This process is also suitable for the reaction of isocyanates with aldehydes to produce amides. The preparation method is cheap in raw material, wide in substrate application range and free of metal catalysts in the reaction process. The initiator or other activator is green and economical, and can effectively reduce the cost.

Method for promoting acylation of amine or alcohol by carbon dioxide

The invention relates to a method for promoting acylation of amine or alcohol by carbon dioxide, which comprises the following steps of: mixing an amine compound, carboxylate or thiocarboxylate compound and a reaction solvent under the action of carbon dioxide, and reacting to obtain an amide compound, or under the action of carbon dioxide, mixing the alcohol compound, the thiocarboxylate compound and the reaction solvent [gamma]-valerolactone, and reacting to obtain the ester compound. According to the invention, under the promotion action of carbon dioxide, carboxylate or thiocarboxylate is used as an acylation reagent, and amine and alcohol are converted into amide and ester compounds in the absence of a transition metal catalyst, so that acylation reagents such as acyl chloride or anhydride with irritation and corrosivity are avoided; and the method has the advantages of simple operation, mild reaction conditions, high tolerance of substrate functional groups, strong applicability and high yield, and provides an efficient, reliable and economical preparation method for synthesis of amide and ester compounds.

Hydrosilylative reduction of primary amides to primary amines catalyzed by a terminal [Ni-OH] complex

A terminal [Ni-OH] complex1, supported by triflamide-functionalized NHC ligands, catalyzes the hydrosilylative reduction of a range of primary amides into primary amines in good to excellent yields under base-free conditions with key functional group tolerance. Catalyst1is also effective for the reduction of a variety of tertiary and secondary amides. In contrast to literature reports, the reactivity of1towards amide reduction follows an inverse trend,i.e., 1° amide > 3° amide > 2° amide. The reaction does not follow a usual dehydration pathway.

NaOTs-promoted transition metal-free C-N bond cleavage to form C-X (X = N, O, S) bonds

Multifunctional transformation of amide C-N bond cleavage is reported. The protocol applies to benzamide, thioamide, alcohols, and mercaptan under similar reaction conditions catalyzed by NaOTs. It is noteworthy that NaOTs can not only be recycled and reused for up to three cycles without significant loss in catalytic activity, but also catalyze gram-grade reactions. This study provides a novel solution with mild conditions and a simple procedure for transformation of multiple amides.

Photocatalyzed Triplet Sensitization of Oximes Using Visible Light Provides a Route to Nonclassical Beckmann Rearrangement Products

Oximes are valuable synthetic intermediates for the preparation of a variety of functional groups. To date, the stereoselective synthesis of oximes remains a major challenge, as most current synthetic methods either provide mixtures of E and Z isomers or furnish the thermodynamically preferred E isomer. Herein we report a mild and general method to achieve Z isomers of aryl oximes by photoisomerization of oximes via visible-light-mediated energy transfer (EnT) catalysis. Facile access to (Z)-oximes provides opportunities to achieve regio- and chemoselectivity complementary to those of widely used transformations employing oxime starting materials. We show an enhanced one-pot protocol for photocatalyzed oxime isomerization and subsequent Beckmann rearrangement that enables novel reactivity with alkyl groups migrating preferentially over aryl groups, reversing the regioselectivity of the traditional Beckmann reaction. Chemodivergent N- or O- cyclizations of alkenyl oximes are also demonstrated, leading to nitrones or cyclic oxime ethers, respectively.

Visible-Light-Promoted Iron-Catalyzed N-Arylation of Dioxazolones with Arylboronic Acids

A visible-light-promoted and simple iron salt-catalyzed N-arylation was achieved efficiently under external photosensitizer-free conditions. Arylboronic acids and bench-stable dioxazolones were used for this cross-coupling reaction. This reaction features high reactivity, wide substrate scope, good functional group tolerance, simple operation procedure, and mild reaction conditions. Preliminary mechanistic investigations were conducted to support a radical pathway. This method may contribute to shift the paradigm of iron-catalyzed C-N bond construction and nitrene transfer chemistry.

An Environmentally Benign, Catalyst-Free N?C Bond Cleavage/Formation of Primary, Secondary, and Tertiary Unactivated Amides

Herein, we report an operationally simple, cheap, and catalyst-free method for the transamidation of a diverse range of unactivated amides furnishing the desired products in excellent yields. This protocol is environmentally friendly and operates under extremely mild conditions without using any promoter or additives. Significantly, this strategy has been implied in the chemoselective synthesis of a pharmaceutical molecule, paracetamol, on a gram-scale with excellent yield. We anticipate that this universally applicable strategy will be of great interest in drug discovery, biochemistry, and organic synthesis.

Photoinduced Carbamoylation of C(sp3)H Bonds with Isocyanates

Alkylbenzenes coupled with isocyanates at the benzylic position upon irradiation with visible light in the presence of an iridium photoredox catalyst, a bromide anion, and a nickel catalyst, producing N-substituted α-aryl amides. An analogous carbamoylation reaction of aliphatic CH bonds of alkanes took place when UV light and a diaryl ketone were used instead of visible light and the iridium complex. The present reaction offers a straightforward and atom-economical method for the synthesis of carboxamides starting from hydrocarbons with one-carbon extension.