6136-68-1

Usage

Uses

Used in Pharmaceutical Industry:
3-Acetylbenzonitrile is used as a synthetic intermediate for the preparation of various pharmaceutical compounds. It is involved in the synthesis of 3-(hydroxyacetyl)benzonitrile and 3-(1-(3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)-4-methylphenylimino)ethyl)benzonitrile, which are important building blocks for the development of new drugs.
Used in Chemical Industry:
In the chemical industry, 3-Acetylbenzonitrile is used in the preparation of (q2-2-Acetyl-4-cyanophenyl)tetra-carbonylmanganese by reacting with benzylpentacarbonylmanganese. 3-ACETYLBENZONITRILE has potential applications in the field of organometallic chemistry and catalysis.
Used in Synthesis of Aromatic Amidoximes:
3-Acetylbenzonitrile is also used in the synthesis of four aromatic amidoximes by reacting hydroxylamine with 1,3-dicyanobenzene, 1,4-dicyanobenzene, 3-acetylbenzonitrile, and 4-acetylbenzonitrile. These amidoximes have potential applications in various chemical and pharmaceutical processes.
Used in Darzens Condensation:
3-Acetylbenzonitrile is utilized in the Darzens condensation process to provide aldehyde, which is a crucial intermediate in the synthesis of various organic compounds, including pharmaceuticals and agrochemicals.

InChI:InChI=1/C26H23Cl2N3O2S/c1-17-4-2-6-21(14-17)29-25(33)23-16-24(32)31(13-12-18-8-10-19(27)11-9-18)26(34-23)30-22-7-3-5-20(28)15-22/h2-11,14-15,23H,12-13,16H2,1H3,(H,29,33)/b30-26-

Upstream product

• 557-21-1 dicyanozinc 
• 2142-63-4 1-(3-Bromophenyl)ethanone 
• 6952-59-6 3-cyanobromobenzene 
• 75-36-5 acetyl chloride 
• 557-21-1 zinc(II) cyanide 
• 14452-30-3 3'-iodoacetophenone 
• 41908-11-6 3-acetylbenzaldehyde 
• 6213-94-1 trimethylsiloxyethene 
• 69113-59-3 3-iodobenzonitrile 
• 75-05-8 acetonitrile 
• 623-26-7 terephthalonitrile 
• 1441-99-2 1-[3-(methylsulfanyl)phenyl]ethan-1-one 
• 64-17-5 ethanol 
• 50916-55-7 3-(2-bromoacetyl)benzonitrile 

Downstream Products

• 107100-94-7 (E)-3-(4-oxo-4-phenylbut-2-enoyl)benzonitrile 
• 60694-93-1 3-acetylbenzenecarboximidimic acid ethyl ester hydrochloride 
• 151646-74-1 4-(3-cyanobenzoyl)-3-hydroxy-2(5H)-furanone 
• 57870-48-1 3-acetylbenzenecarboximidic acid ethyl ester 
• 258525-51-8 (S)-1-(3’-cyanophenyl)ethanol 
• 3174-48-9 p-methylphenoxyl radical 
• 861964-99-0 3-[3-(4-pyridin-2-ylpiperazin-1-yl)propanoyl]benzonitrile 
• 849697-63-8 3-(3-cyano-phenyl)-3-methyl-oxirane-2-carboxylic acid ethyl ester 
• 2362-66-5 m-Acetyl thiobenzamide 
• 534575-99-0 2-[1-(3-Cyano-phenyl)-eth-(Z)-ylidene]-succinic acid 1-ethyl ester 

Relevant academic research and scientific papers

Photoinduced Acetylation of Anilines under Aqueous and Catalyst-Free Conditions

A green and efficient visible-light induced functionalization of anilines under mild conditions has been reported. Utilizing nontoxic, cost-effective, and water-soluble diacetyl as photosensitizer and acetylating reagent, and water as the solvent, a variety of anilines were converted into the corresponding aryl ketones, iodides, and bromides. With advantages of environmentally friendly conditions, simple operation, broad substrate scope, and functional group tolerance, this reaction represents a valuable method in organic synthesis.

Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers

We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications demonstrate its versatility and utility in multistep synthesis.

Synthesis method of aromatic benzyl ketone

The invention discloses a synthesis method of aromatic benzyl ketone, which comprises the following step: by using oxygen and/or air as an oxidant, oxidizing an aromatic benzyl compound shown in a formula (I) under the action of a catalytic system to obtain aromatic benzyl ketone shown in a formula (II). The catalytic system is formed by combining ferric ions, nitrate radicals and N-hydroxyimide derivatives and does not contain heavy metal ions harmful to human bodies, wherein the molar ratio of the ferric ions to the nitrate radicals is 1: (0.5-5), and the molar ratio of the ferric ions to the N-hydroxyimide derivatives is (0.01-0.1): (0.03-0.2). The method disclosed by the invention is wide in substrate applicability and high in atom utilization rate, avoids the use of harmful heavy metals such as copper and cobalt, and has the characteristics of high efficiency, economy and environmental protection. The formulas are as follows: Ar-CH2-R (I) and Ar-CO-R (II).

Selective Synthesis of Secondary and Tertiary Amines by Reductive N-Alkylation of Nitriles and N-Alkylation of Amines and Ammonium Formate Catalyzed by Ruthenium Complex

A new ruthenium catalytic system for the syntheses of secondary and tertiary amines via reductive N-alkylation of nitriles and N-alkylation of primary amines is proposed. Isomeric complexes 8 catalyze transfer hydrogenation and N-alkylation of nitriles in ethanol to give secondary amines. Unsymmetrical secondary amines can be produced by N-alkylation of primary amines with alcohols via the borrowing hydrogen methodology. Aliphatic amines were obtained with excellent yields, while only moderate conversions were observed for anilines. Based on kinetic and mechanistic studies, it is suggested that the rate determining step is the hydrogenation of intermediate imine to amine. Finally, ammonium formate was applied as the amination reagent for alcohols in the presence of ruthenium catalyst 8. Secondary amines were obtained from primary alcohols within 24 hours at 100 °C, and tertiary amines can be produced after prolonged heating. Secondary alcohols can only be converted to secondary amines with moderate yield. Based on mechanistic studies, the process is suggested to proceed through an ammonium alkoxy carbonate intermediate, where carbonate acts as an efficient leaving group.

Preparation method of aromatic ketone

The invention discloses a preparation method of aromatic ketone. Under the effects of a palladium catalyst and a nitrogen-containing ligand, nitrile compounds and arylsulfonylhydrazide take desulfurization addition reaction in an organic solvent; after the reaction is completed, post treatment is performed to obtain aromatic ketone. The reaction is applicable to aromatic nitrile compounds, and isalso applicable to aliphatic nitrile compounds; the reaction realizes the wide substrate applicability and functional group tolerance; the potential application value is realized in the aspect of aryl-carbonyl building.

Pd(II)-Catalyzed Denitrogenative and Desulfinative Addition of Arylsulfonyl Hydrazides with Nitriles

A Pd(II)-catalyzed denitrogenative and desulfinative addition of arylsulfonyl hydrazides with nitriles has been successfully achieved under mild conditions. This transformation is a new method for the addition reaction to nitriles with arylsulfonyl hydrazides as arylating agent, thus providing an alternative synthesis of aryl ketones. The reported addition reaction is tolerant to many common functional groups, and works well in the presence of electron-donating and electron-withdrawing substituents. Notably, the reported denitrogenative and desulfinative addition was also appropriate for alkyl nitriles, making this newly developed transformation attractive.

Catalyst-free, efficient and one pot protocol for synthesis of nitriles from aldehydes using glycerol as green solvent

We described herein the novel, efficient and one-pot catalyst free protocol for the synthesis of nitriles from aldehydes by using hydroxyl amine hydrochlorides in glycerol as a green solvent. This protocol was efficiently used for transformation of aromatic aldehydes bearing electron-withdrawing and electron-donating groups into a aryl nitriles in good to excellent yields. The methodology offers a very simple, efficient and environmentally benign procedure.

Aryl Nitriles from Alkynes Using tert -Butyl Nitrite: Metal-Free Approach to C≡C Bond Cleavage

Alkyne C≡C bond breaking, outside of alkyne metathesis, remains an underdeveloped area in reaction discovery. Recently, nitrogenation has been reported to allow nitrile formation from alkynes. A new protocol for the metal-free C≡C bond cleavage of terminal alkynes to produce nitriles is reported. This method provides an opportunity to synthesize a vast range of nitriles containing aryl, heteroaryl, and natural product derivatives (38 examples). In addition, the potential of tBuONO to act as a powerful nitrogenating agent for terminal aryl alkynes is demonstrated. (Figure Presented).

Rhodium-Catalyzed Transnitrilation of Aryl Boronic Acids with Dimethylmalononitrile

An efficient transnitrilation of aryl boronic acids with dimethylmalononitrile (DMMN) is described. This rhodium-catalyzed electrophilic cyanation presents a novel approach to prepare aryl nitriles by using a carbon-bound cyanating reagent which undergoes cross-coupling with the aryl boronic acid. The reaction expands the degree of functional-group compatibility exhibited by the transnitrilation of aryl Grignard and aryllithium reagents. A variety of aryl boronic acid derivatives and dialkylmalononitriles were amenable to the transnitrilation.

One-pot one-step deracemization of amines using ω-transaminases

In this study, we developed a one-pot one-step deracemization method for the production of various enantiomerically pure amines using two opposite enantioselective ω-TAs. Using this method, various aromatic amines were successfully converted to their (R)-forms (>99%) with good conversion.