10266-42-9

Basic information

• Product Name: 4-acetylphenylacetonitrile
• Synonyms: 4-acetylphenylacetonitrile;Benzeneacetonitrile, 4-acetyl- (9CI);4-Acetylbenzeneacetonitrile;Einecs 233-607-6;2-(4-acetylphenyl)acetonitrile
• CAS NO: 10266-42-9
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.18456
• EINECS: 233-607-6
• Product Categories: ACETYLGROUP
• Mol File: 10266-42-9.mol

Chemical Properties

• Boiling Point: 318.5°Cat760mmHg
• Flash Point: 146.4°C
• Appearance: /
• Density: 1.081g/cm³
• Vapor Pressure: 0.00036mmHg at 25°C
• Refractive Index: 1.533
• CAS DataBase Reference: 4-acetylphenylacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-acetylphenylacetonitrile(10266-42-9)
• EPA Substance Registry System: 4-acetylphenylacetonitrile(10266-42-9)

Safety Data

• Hazardous Substances Data: 10266-42-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-acetylphenylacetonitrile is used as an intermediate for the synthesis of various pharmaceuticals, leveraging its reactivity and functional groups to facilitate the production of a wide range of medicinal compounds.
Used in Agrochemical Industry:
4-acetylphenylacetonitrile serves as an intermediate in the synthesis of agrochemicals, contributing to the development of effective crop protection agents and other agricultural products.
Used in Organic Synthesis:
As a building block in organic synthesis, 4-acetylphenylacetonitrile is utilized for the creation of complex organic molecules, taking advantage of its versatile reactivity to form new chemical entities.
Used in Heterocyclic Compound Preparation:
4-acetylphenylacetonitrile is used as a precursor in the preparation of heterocyclic compounds, which are important in various fields such as pharmaceuticals, materials science, and agrochemicals, due to their unique properties and applications.

InChI:InChI=1/C10H9NO/c1-8(12)10-4-2-9(3-5-10)6-7-11/h2-5H,6H2,1H3

Upstream product

• 54589-56-9 4-chloromethylacetophenone 
• 143-33-9 sodium cyanide 
• 506-96-7 Acetyl bromide 
• 140-29-4 phenylacetonitrile 
• 7446-70-0 aluminium trichloride 
• 51229-51-7 4-acetylbenzyl bromide 
• 18293-53-3 2-trimethylsilylacetonitrile 
• 99-90-1 para-bromoacetophenone 
• 122-00-9 para-methylacetophenone 
• 75633-63-5 4-(hydroxymethyl)acetophenone 
• 408334-58-7 1-(4-hydroxymethyl-phenyl)-ethanone-diethylacetal 
• 928664-98-6 4-isoxazoleboronic acid pinacol ester 
• 99-91-2 para-chloroacetophenone 
• 1071-36-9 sodium cyanoacetate 

Downstream Products

• 7398-52-9 4-acetyl-phenylacetic acid 
• 101576-14-1 [4-(4-chloro-trans-cinnamoyl)-phenyl]-acetonitrile 
• 101600-49-1 (4-trans-cinnamoyl-phenyl)-acetonitrile 
• 109812-60-4 [4-(3-methoxy-cinnamoyl)-phenyl]-acetonitrile 
• 100-21-0 terephthalic acid 
• 141336-20-1 1-(4-Acetylphenyl)cyclopropanecarbonitrile 
• 92132-58-6 [4-[4-(Cyanomethyl)Phenyl]-2-Thiazolyl]Guanidine, Hydrobromide 
• 878556-00-4 tert-butyl ([(4-acetylphenyl)acetyl]{2-[(9H-fluoren-9-ylmethoxycarbonyl)amino]ethyl}amino)acetate 

Relevant articles and documents

Direct C(sp3)-H Cyanation Enabled by a Highly Active Decatungstate Photocatalyst

A highly efficient, direct C(sp3)-H cyanation was developed under mild photocatalytic conditions. The method enabled the direct cyanation of various C(sp3)-H substrates with excellent functional group tolerance. Notably, complex natural products and bioactive compounds were efficiently cyanated.

Assembly of α-(Hetero)aryl Nitriles via Copper-Catalyzed Coupling Reactions with (Hetero)aryl Chlorides and Bromides

α-(Hetero)aryl nitriles are important structural motifs for pharmaceutical design. The known methods for direct synthesis of these compounds via coupling with (hetero)aryl halides suffer from narrow reaction scope. Herein, we report that the combination of copper salts and oxalic diamides enables the coupling of a variety of (hetero)aryl halides (Cl, Br) and ethyl cyanoacetate under mild conditions, affording α-(hetero)arylacetonitriles via one-pot decarboxylation. Additionally, the CuBr/oxalic diamide catalyzed coupling of (hetero)aryl bromides with α-alkyl-substituted ethyl cyanoacetates proceeds smoothly at 60 °C, leading to the formation of α-alkyl (hetero)arylacetonitriles after decarboxylation. The method features a general substrate scope and is compatible with various functionalities and heteroaryls.

2,7-DIAZASPIRO[4.4]NONANES

The present invention covers 2,7-diazaspiro[4.4]nonane compounds of general formula (I): in which n, X, R2, R3, R4, R5, R6a and R6b are as defined herein, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular of cancer or diabetes, as a sole agent or in combination with other active ingredients.

Two-step cyanomethylation protocol: Convenient access to functionalized aryl- and heteroarylacetonitriles

A two-step protocol has been developed for the introduction of cyanomethylene groups to metalated aromatics through the intermediacy of substituted isoxazoles. A palladium-mediated cross-coupling reaction was used to introduce the isoxazole unit, followed by release of the cyanomethylene function under thermal or microwave-assisted conditions. The intermediate isoxazoles were shown to be amenable to further functionalization prior to deprotection of the sensitive cyanomethylene motif, allowing access to a wide range of aryl- and heteroaryl-substituted acetonitrile building blocks.

Synthesis of α-aryl esters and nitriles: Deaminative coupling of α-aminoesters and α-aminoacetonitriles with arylboronic acids

Transition-metal-free synthesis of α-aryl esters and nitriles using arylboronic acids with α-aminoesters and α-aminoacetonitriles, respectively, as the starting materials has been developed. The reaction represents a rare case of converting C(sp3)-N bonds into C(sp3)-C(sp2) bonds. The reaction conditions are mild, demonstrate good functional-group tolerance, and can be scaled up. Touch base: A transition-metal-free protocol for the synthesis of α-aryl esters and nitriles by deaminative coupling is presented. Strong bases and transition-metal catalysts are not needed. The new synthetic method uses readily available starting materials and demonstrates wide substrate scope.

Synthesis of α-Aryl nitriles through palladium-catalyzed decarboxylative coupling of cyanoacetate salts with aryl halides and triflates

Worth its salt: The palladium-catalyzed decarboxylative coupling of the cyanoacetate salt as well as its mono- and disubstituted derivatives with aryl chlorides, bromides, and triflates is described (see scheme). This reaction is potentially useful for the preparation of a diverse array of α-aryl nitriles and has good functional group tolerance. S-Phos=2-(2,6- dimethoxybiphenyl)dicyclohexylphosphine), Xant-Phos=4,5-bis(diphenylphosphino)- 9,9-dimethylxanthene. Copyright

Palladium-catalyzed cyanomethylation of aryl halides through domino Suzuki coupling-isoxazole fragmentation

A one-pot protocol for the cyanomethylation of aryl halides through a palladium-catalyzed reaction with isoxazole-4-boronic acid pinacol ester was developed. Mechanistically, the reaction proceeds through (1) Suzuki coupling, (2) base-induced fragmentation, and (3) deformylation as shown by characterization of all postulated intermediates. Under optimized conditions (PdCl2dppf, KF, DMSO/H2O, 130 °C) a broad spectrum of aryl bromides could be converted into arylacetonitriles with up to 88% yield.

PNA-based reagents for the direct and site-specific synthesis of thymine dimer lesions in genomic DNA

An acetophenone containing PNA-based reagent was designed for the direct and site-specific synthesis of a cis-syn thymidine dimer lesion in genomic DNA. Copyright

Mild palladium-catalyzed selective monoarylation of nitriles

Two new palladium-catalyzed procedures for the arylation of nitriles under less basic conditions than previously reported have been developed. The selective monoarylation of acetonitrile and primary nitriles has been achieved using α-silyl nitriles in the presence of ZnF2. This procedure is compatible with a variety of functional groups, including cyano, keto, nitro, and ester groups, on the aryl bromide. The arylation of secondary nitriles occurred in high yield by conducting reactions with zinc cyanoalkyl reagents. These reaction conditions tolerated base-sensitive functional groups, such as ketones and esters. The combination of these two methods, one with a-silyl nitriles and one with zinc cyanoalkyl reagents, provides a catalytic route to a variety of benzylic nitriles, which have not only biological significance but utility as synthetic intermediates. The utility of these new coupling reactions has been demonstrated by a synthesis of verapamil, a clinically used drug for the treatment of heart disease, by a three-step route from commercial materials that allows convenient variation of the aryl group.

Efficient photodecarboxylation of aroyl-substituted phenylacetic acids in aqueous solution: A general photochemical reaction

Photolysis (254-350 nm) of a variety of aroyl-substituted phenylacetic acids and p-acetylphenylacetic acid in aqueous solution at pH > pK(a) resulted in efficient photodecarboxylation (Φ = 0.2-0.7), to give in most cases a single product arising via the corresponding arylmethyl carbanion, indicating that photodecarboxylation is an efficient and general reaction for these types of compounds.