884504-20-5

Basic information

• Product Name: 3,4-DIMETHYLBENZOYLACETONITRILE
• Synonyms: 3,4-DIMETHYLBENZOYLACETONITRILE
• CAS NO: 884504-20-5
• Molecular Formula: C₁₁H₁₁NO
• Molecular Weight: 173.21
• Mol File: 884504-20-5.mol

Chemical Properties

• Boiling Point: 344.3°C at 760 mmHg
• Flash Point: 162°C
• Appearance: /
• Density: 1.06g/cm³
• Vapor Pressure: 6.66E-05mmHg at 25°C
• Refractive Index: 1.53
• CAS DataBase Reference: 3,4-DIMETHYLBENZOYLACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIMETHYLBENZOYLACETONITRILE(884504-20-5)
• EPA Substance Registry System: 3,4-DIMETHYLBENZOYLACETONITRILE(884504-20-5)

Safety Data

• Hazardous Substances Data: 884504-20-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
3,4-Dimethylbenzoylacetonitrile is used as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals due to its ability to form carbon-carbon bonds and its role in the preparation of heterocyclic compounds. Its reactivity and structural properties make it an essential component in the development of new and effective drugs and agricultural products.
Used in Organic Synthesis:
In the realm of organic synthesis, 3,4-Dimethylbenzoylacetonitrile is utilized as a reagent, particularly for the formation of carbon-carbon bonds. Its unique structure allows for the creation of complex organic molecules, contributing to the advancement of organic chemistry.
Used in Dye and Pigment Production:
3,4-Dimethylbenzoylacetonitrile is also employed in the production of dyes and pigments, where its chemical properties contribute to the development of specialty chemicals with specific color and stability characteristics. This application highlights its versatility beyond pharmaceutical and agrochemical synthesis.
Used in Specialty Chemicals Production:
3,4-DIMETHYLBENZOYLACETONITRILE's diverse applications extend to the production of specialty chemicals, where its unique properties are harnessed to create high-value products for various industries, further emphasizing its importance in the chemical sector.

InChI:InChI=1/C11H11NO/c1-8-3-4-10(7-9(8)2)11(13)5-6-12/h3-4,7H,5H2,1-2H3

Upstream product

• 18293-53-3 2-trimethylsilylacetonitrile 
• 201230-82-2 carbon monoxide 
• 31599-61-8 3,4-dimethyliodobenzene 
• 38404-42-1 methyl 3,4-dimethylbenzoate 
• 75-05-8 acetonitrile 
• 13138-21-1 diazoacetonitrile 
• 5973-71-7 3,4-dimethylbenzaldehyde 
• 13939-06-5 molybdenum hexacarbonyl 

Downstream Products

• 1556864-79-9 3-(3,4-dimethylphenyl)-6,7-dimethyl-5,8-dinitro-2-naphthonitrile 
• 1556864-68-6 5,8-dibromo-3-(3,4-dimethylphenyl)-2-naphthonitrile 
• 1556864-60-8 3-(3,4-dimethylphenyl)-6,7-dimethyl-2-naphthonitrile 
• 1556864-49-3 3-(4-bromophenyl)-2-naphthonitrile-3-(3,4-dimethylphenyl)-2-naphthonitrile 

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.

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.

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.

Synthesis of benzoylacetonitriles from Pd-catalyzed carbonylation of aryl iodides and trimethylsilylacetonitrile

Palladium-catalyzed carbonylation of aryl iodides and trimethylsilylacetonitrile to produce benzoylacetonitrile derivatives through a one-pot, three-component reaction is described. This preparation method provides good yields of the carbonylated products without any additional ligands. It has a broad substrate scope with a high tolerance for a variety of functional groups.