54959-85-2

Usage

Chemical Class

Aromatic nitrile

Physical State

White solid

Molecular Weight

217.65 g/mol

Uses

Organic Synthesis: Used as a building block in organic synthesis.
Pharmaceutical Research: Employed as an intermediate in pharmaceutical research.
Agrochemicals: Utilized in the production of various agrochemicals.
Dyes: Used in the manufacturing process of dyes.
Reagent: Functions as a reagent in organic chemistry reactions to introduce the cyano group into organic molecules.

Safety Precautions

Handle with care as it can be harmful if ingested, inhaled, or comes into contact with the skin.

InChI:InChI=1/C11H10ClNO/c12-10-6-4-9(5-7-10)11(14)3-1-2-8-13/h4-7H,1-3H2

Upstream product

• 151-50-8 potassium cyanide 
• 40877-09-6 4-chloro-1-(4-chlorophenyl)butan-1-one 
• 1402927-11-0 ethyl 2-(4-chlorobenzoyl)-4-cyanobutanoate 
• 2881-63-2 ethyl (4-chlorobenzoyl)acetate 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 29480-09-9 1-(4-chlorophenyl)cyclobutan-1-ol 
• 122-01-0 4-chloro-benzoyl chloride 
• 1679-18-1 4-Chlorophenylboronic acid 
• 25917-55-9 4-cyano-N-phenylbutanamide 
• 544-13-8 Glutaronitrile 

Downstream Products

• 81152-93-4 7-Chloro-5-phenyl-1,3,4,5-tetrahydro-indeno[1,2-b]pyridin-2-one 
• 327617-83-4 2-(4-chloro-phenyl)-tetrahydro-furan-2-carboxylic acid 
• 54959-79-4 (4aR,5R,9bR)-7-Chloro-5-phenyl-1,3,4,4a,5,9b-hexahydro-indeno[1,2-b]pyridin-2-one 
• 1274820-16-4 2-hydroxy-2-(4-chlorophenyl)cyclopentanone 
• 1402926-97-9 (S)-2-(4-chlorophenyl)-2-hydroxycyclopentanone 

Relevant academic research and scientific papers

Syntheses of Pyrroles, Pyridines, and Ketonitriles via Catalytic Carbopalladation of Dinitriles

The first example of the Pd-catalyzed addition of organoboron reagents to dinitriles, as an efficient means of preparing 2,5-diarylpyrroles and 2,6-diarylpyridines, has been discussed here. Furthermore, the highly selective carbopalladation of dinitriles with organoboron reagents to give long-chain ketonitriles has been developed as well. Based on the broad scope of substrates, excellent functional group tolerance, and use of commercially available substrates, the Pd-catalyzed addition reaction of arylboronic acid and dinitriles is expected to be significant in future synthetic procedures.

Palladium-Catalyzed Cascade Reactions of I-Ketonitriles with Arylboronic Acids: Synthesis of Pyridines

This study presents the first example of the Pd-catalyzed cascade reactions of 5-oxohexanenitrile with arylboronic acids, affording important synthon 2-methylpyridines that can be further translated through C(sp3)-H functionalization to construct pyridine derivatives. Furthermore, this chemistry allows 5-oxo-5-Arylpentanenitrile to react with arylboronic acids to provide unsymmetrical 2,6-diarylpyridines. This protocol paves the way for the practical and atom economical syntheses of valuable pyridines with broad functional groups in moderate to excellent yields under mild conditions.

A Novel Ketonitrile Synthesis by Palladium-Catalyzed Carbonylative Coupling Reactions of Amides with Arylboronic Acids

A novel, efficient, and simple procedure to synthesize diverse ketonitriles by palladium-catalyzed Suzuki coupling of amides through N–C cleavage has been developed. This procedure features mild conditions, a broad substrate scope, and easily prepared substrates, providing a simple and efficient access to a variety of ketonitriles.

Nickel-Catalyzed Reductive Electrophilic Ring Opening of Cycloketone Oxime Esters with Aroyl Chlorides

By merging cross-electrophile coupling and C-C bond cleavage, we developed a Ni-catalyzed electrophilic ring opening of cycloketone oxime esters with aromatic acid chlorides in assistance of Mn as reductant. Notably, complete regioselectivity can be achieved in this C-C bond cleavage reaction, providing an efficient access to a variety of cyanoketones under cyanide-free conditions. A radical reaction pathway was proposed on the basis of the results of the mechanistic probing experiments.

C-C Bond-Forming Strategy by Manganese-Catalyzed Oxidative Ring-Opening Cyanation and Ethynylation of Cyclobutanol Derivatives

A novel C-C bond-forming strategy employing manganese-catalyzed ring-opening of cyclobutanol substrates, followed by cyanation or ethynylation, is described. A cyano C1 unit and ethynyl C2 unit are regiospecifically introduced to the γ-position of ketones at room temperature, providing a mild yet powerful method for production of elusive aliphatic nitriles and alkynes. All transformations described are based on a common sequence: 1) oxidative ring-opening of cyclobutanol substrates by C-C bond cleavage; 2) radical addition to triple bonds bearing an arylsulfonyl group; and 3) radical-mediated C-S bond cleavage.

Enantioselective titanium(III)-catalyzed reductive cyclization of ketonitriles

Reduction, please! The title reaction affords ?-hydroxyketones, a common structural motif in biologically active natural products, in good yields and high enantioselectivities at room temperature. The commercially available ansa-titanocene 1 was found to be an efficient catalyst for this process, which presumably proceeds by addition of a ketyl radical to a nitrile.

Substituted tetrahydrofuroyl-1-phenylalanine derivatives as potent and specific VLA-4 antagonists

A series of substituted tetrahydrofuroyl-1-phenylalanine derivatives was prepared and evaluated as VLA-4 antagonists. Substitution of the α carbon of the tetrahydrofuran with aryl groups increased the specificity for VLA-4 versus α4β7 while amide substitution increased the potency of the series without increasing the specificity. Substitution of the β carbon of the tetrahydrofuran with keto or amino groups slightly improved the specificity for VLA-4 versus α4β7 but with a significant loss in binding affinity for VLA-4.