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
• Article Data: 14

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

General Description

3-Methylbenzoylacetonitrile is a chemical compound that exists in a solid state and falls under the category of organic compounds. It has a molecular formula of C11H9NO and a molecular weight of 171.194 g/mol. The compound has a benzene ring in its structure, indicative of its aromatic characteristics. It is typically used in organic synthesis and, like all nitriles, carries a cyano functional group (-C≡N). However, there is not much accessible information about the specifics of its use or its effects on health and the environment. As with all chemicals, it should be handled responsibly, with adequate safety measures in place.

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

Upstream product

• 99-36-5 1-methoxycarbonyl-3-methylbenzene 
• 75-05-8 acetonitrile 
• 18293-53-3 2-trimethylsilylacetonitrile 
• 201230-82-2 carbon monoxide 
• 625-95-6 3-Iodotoluene 
• 13138-21-1 diazoacetonitrile 
• 620-23-5 m-tolyl aldehyde 
• 7677-24-9 trimethylsilyl cyanide 
• 59790-58-8 trimethyl[1-(3-methylphenyl)vinyloxy]silane 
• 587-03-1 3-methylbenzyl alcohol 
• 13939-06-5 molybdenum hexacarbonyl 
• 585-74-0 3-Methylacetophenone 
• 143-33-9 sodium cyanide 
• 51012-64-7 2-bromo-3'-methylacetophenone 

Downstream Products

• 80568-96-3 5-m-tolyl-2H-pyrazol-3-ylamine 
• 357284-73-2 2-Amino-4-(methylthio)-6-m-tolyl-pyrimidine-5-carbonitrile 
• 1476782-04-3 5-(m-tolyl)furan-2,3,4-tricarbonitrile 
• 144660-10-6 2,2-dichloro-1-(3-methylphenyl)ethanone 
• 136125-68-3 methyl 3-methylphenylglyoxylate 

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.

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.

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).