3441-01-8

Usage

Uses

Used in Chemical Synthesis:
3-Cyano-Benzamide is used as a synthetic intermediate for the production of other organic compounds. Its unique structure allows it to be a versatile building block in the synthesis of various chemical entities.
Used in Pharmaceutical Industry:
3-Cyano-Benzamide is used as a starting material in the development of new pharmaceutical compounds. Its reactivity and structural features make it a valuable component in the design and synthesis of potential drug candidates.
Used in Research Applications:
3-Cyano-Benzamide is used as a research chemical in academic and industrial laboratories. It serves as a model compound for studying the properties and reactions of aromatic amides and cyano groups, contributing to the advancement of chemical knowledge and technology.
Used in Material Science:
3-Cyano-Benzamide is used in the development of new materials with specific properties, such as in the creation of novel polymers or as a component in the synthesis of advanced materials with potential applications in various industries.

InChI:InChI=1/C8H6N2O/c9-5-6-2-1-3-7(4-6)8(10)11/h1-4H,(H2,10,11)

Upstream product

• 626-17-5 benzene-1,3-dicarbonitrile 
• 1740-57-4 isophthalamide 
• 108-38-3 m-xylene 
• 1711-11-1 3-cyanobenzoyl chloride 
• 24964-64-5 3-Cyanobenzaldehyde 
• 1877-72-1 3-Cyanobenzoic acid 
• 75-05-8 acetonitrile 
• 46133-07-7 benzene-1,3-dicarboxladehyde dioxime 

Downstream Products

• 1877-72-1 3-Cyanobenzoic acid 
• 1740-57-4 isophthalamide 
• 78950-37-5 m-cyanothiobenzamide 

Relevant academic research and scientific papers

From 1,3-dicyanobenzene to 3-cyanobenzamide - Its molecular structure in the gas-phase and in the crystal

The crystals of 3-cyanobenzamide have been obtained in the reaction of MgPcH2O with 1,3-dicyanobenzene. 3-Cyanobenzamide crystallises in the P21/c space group of the monoclinic system with four molecules per unit cell. In the crystal, the 3-cyanobenzamide molecule is non-planar, the amide group is rotated by 21.8(1)° around the Car-Csp2 bond in relation to the phenyl ring. Full optimised molecular orbital calculations performed on the isolated 3-cyanobenzamide molecule have shown a similar conformation (the rotation angle equals to 22.46°). Two pairs of symmetric equivalent N-H?O and N-H?N hydrogen bonds with two neighbouring form pseudo one-dimensional chains interconnect each 3-cyanobenzamide molecule in the crystal. The chains of 3-cyanobenzamide molecules form a stacking structure with π?π interactions between the aromatic phenyl rings within the stacks. The molecular orbital calculations and conformational analysis have shown two equivalent pairs minimum of energy on the potential energy surface (PES) - one global, other local. During rotation of the amide group from 0 to 360° around the Car-Csp2 bond four rotation barriers are observed. The highest rotation barrier energy of 48.84 kJ mol-1 is compared to the hydrogen bond energy.

Mechanochemical synthesis of half-sandwich iridium/rhodium complexes with 8-hydroxyquinoline derivatives ligands

Mechanochemistry provides a rapid, efficient route to half-sandwich iridium and rhodium complexes from [MCp*(μ-Cl)Cl]2 (M = Ir, Rh) and 8-hydroxyquinoline-2-carbaldehyde without the need for Schlenk manipulation, inert gas protection, or dry solvents. Furthermore, post-synthetic modification of the half-sandwich metal complexes has been carried out via a mechanochemical Wittig reaction between half-sandwich metal complex and phosphorus ylide. All complexes were fully characterized by 1H and 13C NMR spectra, infrared spectroscopy, mass spectrometry, and single-crystal X-ray diffraction method. The half-sandwich rhodium complexes exhibited high catalytic activity towards the amide synthesis between aldehyde and hydroxylamine hydrochloride (NH2OH·HCl) with a broad functional group tolerance.

Visible light-mediated synthesis of amides from carboxylic acids and amine-boranes

Here, a photocatalytic deoxygenative amidation protocol using readily available amine-boranes and carboxylic acids is described. This approach features mild conditions, moderate-to-good yields, easy scale-up, and up to 62 examples of functionalized amides with diverse substituents. The synthetic robustness of this method was also demonstrated by its application in the late-stage functionalization of several pharmaceutical molecules.

One-Pot Anodic Conversion of Symmetrical Bisamides of Ethylene Diamine to Unsymmetrical gem-Bisamides of Methylene Diamine

Symmetrical bisamides of ethylene diamine of type ArCONHCH2CH2NHCOAr undergo anodic C-C bond cleavage in acetonitrile-LiClO4 under controlled-potential electrolysis. The electrogenerated carbocation intermediates react with the solvent acetonitrile to afford unsymmetrical gem-bisamides of type ArCONHCH2NHCOMe in a one-pot reaction. The yields of the latter products are moderate (up to 60%). Other minor products involve two symmetrical gem-bisamides of type ArCONHCH2NHCOAr and MeCONHCH2NHCOMe and fragmentation products (e.g., ArCONHCHO, ArCONH2, and ArCN).

Method for preparing derivatives of benzamide under microwave condition in aqueous phase

The invention discloses a method for preparing derivatives of benzamide under a microwave condition in an aqueous phase. A coupling reaction is carried out between substituted benzoic acid and amine under the microwave condition in the aqueous phase. The method for preparing the derivatives of benzamide is environmentally friendly, easy and convenient to operate, safe, low in cost and efficient. Compared with the prior art, the method can be applicable to a large number of functional groups, is high in yield, produces fewer by-products, and further is easy to operate, safe, low in cost and environmentally friendly. A formula is shown in the description.

Efficient Bimetallic Catalysis of Nitrile Hydration to Amides with a Simple Pd(OAc)2/Lewis Acid Catalyst at Ambient Temperature

Transition-metal-catalyzed nitrile hydration is an atom-economic method for the synthesis of various amides. This work demonstrates for the first time that the addition of non-redox metal ions like Sc3+ dramatically accelerate the hydration of various nitriles to amides at ambient temperature with the simple Pd(OAc)2 salt as catalyst, whereas the reactions with Pd(OAc)2 alone were very sluggish. The formation of a heterobimetallic PdII/ScIII species has been proposed as the key species for the hydration that demonstrates a bimetallic synergistic effect in this process.

Supported Gold Nanoparticles-Catalyzed Microwave-Assisted Hydration of Nitriles to Amides under Base-Free Conditions

Polystyrene-supported gold (Au@PS) nanoparticles were synthesized by the reduction deposition approach and well characterized by UV-visible, XRD, TEM, SAED, EDX, and XPS studies. The Au@PS was applied as catalyst for the hydration of nitriles to amides in water under microwave irradiation. Several functionalized aromatic, heterocyclic and aliphatic nitriles were found to be active for synthesis of the corresponding amides where no activation of water by base, ligand and support is needed. Easy recovery, negligible leaching and recyclability for up to eight runs are added advantages of the catalyst under water-mediated reaction conditions. (Figure presented.).

Homogeneous and stereoselective copper(II)-catalyzed monohydration of methylenemalononitriles to 2-cyanoacrylamides

A facile and efficient route for the homogeneous and highly stereoselective monohydration of substituted methylenemalononitriles to (E)-2-cyanoacrylamides catalyzed by copper(II) acetate monohydrate in acetic acid containing 2% water is described, and a mechanism is proposed. The protocol has proved to be suitable for the monohydration of dicyanobenzenes and 2-substituted malononitriles.

Solid-supported ruthenium(0): An efficient heterogeneous catalyst for hydration of nitriles to amides under microwave irradiation

Solid-supported ruthenium(0) was synthesized by the reduction deposition method and used as a heterogeneous catalyst for the hydration of nitriles to amides under microwave irradiation. A wide range of aromatic, α,β-unsaturated and aliphatic nitriles were efficiently converted to their corresponding primary amides under milder conditions. The catalyst was found to be very stable under moisture and microwave irradiation, easily separable from the reaction mixture, to cause negligible metal contamination of the product and was recyclable up to ten times without significant loss of catalytic activity.

Transition metal-free sodium borohydride promoted controlled hydration of nitriles to amides

A transition metal-free process, promoted by sodium borohydride, has been developed for convenient and selective hydration of nitriles to corresponding amides. The present process converts the aromatic, aliphatic, and heteroaromatic nitriles with wide functional group tolerance. The regioselective hydration of one nitrile moiety in the presence of an other nitrile group makes high impact in the present protocol.