53882-81-8

Basic information

• Product Name: 3-Methylbenzoylacetonitrile
• Synonyms: 3-METHYLBENZOYLACETONITRILE;3-TOLUOYLACETONITRILE;3-OXO-3-M-TOLYLPROPANENITRILE;3-(3-METHYLPHENYL)-3-OXOPROPANENITRILE;BUTTPARK 94\04-26;m-Toluoylacetonitrile, 97%;3-Methyl-b-oxo-benzenepropanenitrile
• CAS NO: 53882-81-8
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.18
• Mol File: 53882-81-8.mol

Chemical Properties

• Melting Point: 73 °C
• Boiling Point: 318.6 °C at 760 mmHg
• Flash Point: 146.5 °C
• Appearance: powder
• Density: 1.081 g/cm³
• Vapor Pressure: 0.000358mmHg at 25°C
• Refractive Index: 1.532
• Storage Temp.: 2-8°C
• PKA: 7.84±0.10(Predicted)
• BRN: 2717335
• CAS DataBase Reference: 3-Methylbenzoylacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methylbenzoylacetonitrile(53882-81-8)
• EPA Substance Registry System: 3-Methylbenzoylacetonitrile(53882-81-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-36/37/39
• RIDADR: 3439
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 53882-81-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-Methylbenzoylacetonitrile is used as a key intermediate in the synthesis of various organic compounds. Its presence in the structure allows for the formation of different functional groups, making it a versatile building block in the creation of complex molecules.
Used in Pharmaceutical Industry:
3-Methylbenzoylacetonitrile is used as a starting material for the synthesis of pharmaceutical compounds. Its unique structure and reactivity enable the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
3-Methylbenzoylacetonitrile is used as a research compound in academic and industrial laboratories. Its properties and reactivity are studied to gain insights into the behavior of nitriles and aromatic compounds, which can lead to the discovery of new chemical reactions and applications.

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

Upstream product

• 120-33-2 ethyl 3-methylbenzoate 
• 75-05-8 acetonitrile 
• 99-36-5 1-methoxycarbonyl-3-methylbenzene 
• 143-33-9 sodium cyanide 
• 51012-64-7 2-bromo-3'-methylacetophenone 
• 585-74-0 3-Methylacetophenone 
• 18293-53-3 2-trimethylsilylacetonitrile 
• 201230-82-2 carbon monoxide 
• 625-95-6 3-Iodotoluene 
• 13939-06-5 molybdenum hexacarbonyl 
• 587-03-1 3-methylbenzyl alcohol 
• 7677-24-9 trimethylsilyl cyanide 
• 59790-58-8 trimethyl[1-(3-methylphenyl)vinyloxy]silane 
• 13138-21-1 diazoacetonitrile 

Downstream Products

• 80568-96-3 5-m-tolyl-2H-pyrazol-3-ylamine 
• 934340-21-3 C₁₃H₁₃NO₃ 
• 357284-73-2 2-Amino-4-(methylthio)-6-m-tolyl-pyrimidine-5-carbonitrile 
• 1401051-57-7 4-methyl-2,3,7,8-tetraphenylnaphtho[1,8-bc]pyran-9-carbonitrile 
• 1401051-64-6 6-methyl-2,3,7,8-tetraphenylnaphtho[1,8-bc]pyran-9-carbonitrile 
• 1426916-66-6 3-(3-methylphenyl)quinoxaline-2-carbonitrile-1,4-dioxide 
• 1426916-74-6 7-methyl-3-(3-methylphenyl)quinoxaline-2-carbonitrile-1,4-dioxide 
• 1426916-80-4 7-methoxy-3-(3-methylphenyl)quinoxaline-2-carbonitrile-1,4-dioxide 
• 1426916-84-8 7-chloro-3-(3-methylphenyl)quinoxaline-2-carbonitrile-1,4-dioxide 
• 1435943-38-6 methyl 5-cyano-6-(3-methylphenyl)-2-hydroxy-4-phenyl-3,4-dihydro-2H-pyran-2-carboxylate 

Relevant articles and documents

Asymmetric Hydroacylation Involving Alkene Isomerization for the Construction of C3-Chirogenic Center

A new transformation pattern for enantioselective intramolecular hydroacylation has been developed involving an alkene isomerization strategy. Proceeding through a five-membered rhodacycle intermediate, 3-enals were converted to C3- or C3,C5-chirogenic cyclopentanones with satisfactory yields, diastereoselectivities, and enantioselectivities. A catalytic cycle has been theoretically calculated and the origin of the stereoselection is rationally explained.

Synthesis and Structure-Activity Relationship of Dual-Stage Antimalarial Pyrazolo[3,4- b]pyridines

Malaria remains one of the most deadly infectious diseases, causing hundreds of thousands of deaths each year, primarily in young children and pregnant mothers. Here, we report the discovery and derivatization of a series of pyrazolo[3,4-b]pyridines targeting Plasmodium falciparum, the deadliest species of the malaria parasite. Hit compounds in this series display sub-micromolar in vitro activity against the intraerythrocytic stage of the parasite as well as little to no toxicity against the human fibroblast BJ and liver HepG2 cell lines. In addition, our hit compounds show good activity against the liver stage of the parasite but little activity against the gametocyte stage. Parasitological profiles, including rate of killing, docking, and molecular dynamics studies, suggest that our compounds may target the Qo binding site of cytochrome bc1.

Catalytic Activation of 1-Cyano-3,3-dimethyl-3-(1H)-1,2-benziodoxole with B(C6F5)3 Enabling the Electrophilic Cyanation of Silyl Enol Ethers

The Lewis acidic activation of a hypervalent iodine reagent containing a transferable cyano group, 1-cyano-3,3-dimethyl-3-(1H)-1,2-benziodoxole (CDBX), with B(C6F5)3, to achieve the catalytic electrophilic cyanation of silyl enol ethers is presented. Mechanistic studies indicate that CDBX is activated through coordination of its cyano group to B(C6F5)3, thus enabling the electrophilic cyanation reaction to occur.

One-pot dichlorinative deamidation of primary β-ketoamides

An approach to the dichlorinative deamidation of primary β-ketoamides through ketonic cleavage is described, and a series of α,α-dichloroketones were furnished mostly in the presence of TEMPO. Based on control experiments, a mechanism involving tandem dichlorination and deamidation is proposed to interpret the observed reactivity.

Palladium-Catalyzed Carbonylative α-Arylation of tert -Butyl Cyanoacetate with (Hetero)aryl Bromides

A three-component coupling protocol has been developed for the generation of 3-oxo-3-(hetero)arylpropanenitriles via a carbonylative palladium-catalyzed α-arylation of tert-butyl 2-cyanoacetates with (hetero)aryl bromides followed by an acid-mediated decarboxylation step. Through the combination of only a stoichiometric loading of carbon monoxide and mild basic reaction conditions such as MgCl2 and dicyclohexylmethylamine for the deprotonation step, an excellent functional group tolerance was ensured for the methodology. Through the use of 13C-labeled carbon monoxide generated from 13COgen, the corresponding 13C-isotopically labeled β-ketonitriles were obtained, and these products could subsequently be converted into cyanoalkynes and 3-cyanobenzofurans with site specific 13C-isotope labeling. (Chemical Equation Presented).

Umpolung Strategy for Synthesis of β-Ketonitriles through Hypervalent Iodine-Promoted Cyanation of Silyl Enol Ethers

An efficient method to synthesize β-ketonitriles from silyl enol ethers by an umploung hypervalent iodine(III)-CN species generated in situ from PhIO/BF3·Et2O/TMSCN has been developed for the first time. This method can be applied to structurally diverse aromatic and aliphatic substrates and further extended to preparation of bioactive compounds like 5-aminopyrazole and 5-aminoisoxazole.

Specific 1,2-Hydride Shift in the Boron Trifluoride Catalyzed Reactions of Aromatic Aldehydes with Diazoacetonitrile: Simple Synthesis of β-Ketonitriles

A series of β-ketonitriles was synthesized within 30 min under mild conditions through the BF3 ·OEt2-catalyzed addition reactions of diazoacetonitrile to aromatic aldehydes and subsequent 1,2-hydride shift. This method is advantageous in that it is operationally simple, mild and metal-free conditions are used, the substrate scope is wide, and the products are obtained in moderate to high yields (up to 81 %). Additionally, γ,δ-unsaturated β-ketonitriles are also accessible by this method by using cinnamaldehydes.

Copper-catalyzed Aerobic Oxidative coupling of Aromatic Alcohols and Acetonitrile to β-Ketonitriles

A practical, convenient, and cheap coppercatalyzed aerobic oxidative coupling of aromatic alcohols and acetonitrile to β-ketonitriles has been developed. The green C-C bond formation involving the loss of two hydrogen atoms from the corresponding two carbons, respectively, unlocks opportunities for markedly different synthetic strategies.

Cascade synthesis of 3-aza-bicyclo[3.1.0]hex-2-ene derivatives from N-allyl enamines

An efficient iodine-mediated cascade synthesis of 3-aza-bicyclo[3.1.0]hex-2-ene derivatives from easily prepared N-allyl enamines has been developed. The advantages of the reaction include facilitative preparation of substrates 3a-t, good functional group tolerance and transition-metal-free conditions.

Palladium-catalyzed carbonylation with Mo(CO)for the synthesis of benzoylacetonitriles

Benzoylacetonitriles were synthesized by the palladium-catalyzed carbonylation of aryl iodides and trimethylsilylacetonitrile using Mo(CO)as a carbon monoxide source. Pd(PPhCland CuFwere employed as the catalyst and activator, respectively. A variety of aryl iodides bearing alkyl, alkoxy, fluoro, chloro, bromo, nitrile, ester, and ketone groups afforded the corresponding benzoylacetonitriles in moderate to good yields. Georg Thieme Verlag Stuttgart ? New York.