34403-03-7

Basic information

• Product Name: 2-(3-METHYLPHENYL)ACETOPHENONE
• Synonyms: 2-(3-METHYLPHENYL)ACETOPHENONE
• CAS NO: 34403-03-7
• Molecular Formula: C₁₅H₁₄O
• Molecular Weight: 210.27
• Mol File: 34403-03-7.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 337.3°C at 760 mmHg
• Flash Point: 144.7°C
• Appearance: /
• Density: 1.062g/cm³
• Vapor Pressure: 0.000106mmHg at 25°C
• Refractive Index: 1.576
• CAS DataBase Reference: 2-(3-METHYLPHENYL)ACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-METHYLPHENYL)ACETOPHENONE(34403-03-7)
• EPA Substance Registry System: 2-(3-METHYLPHENYL)ACETOPHENONE(34403-03-7)

Safety Data

• Hazardous Substances Data: 34403-03-7(Hazardous Substances Data)

Usage

Type of Compound

Ketone

Usage

Flavoring agent, fragrance, pharmaceutical production, organic synthesis intermediate

Aroma

Sweet, floral

Physical State

Colorless to pale yellow liquid

Melting Point

23-24°C

Boiling Point

275-276°C

Potential Applications

Antioxidant, materials science

InChI:InChI=1/C15H14O/c1-12-6-5-7-13(10-12)11-15(16)14-8-3-2-4-9-14/h2-10H,11H2,1H3

Upstream product

• 16717-64-9 1-azidostyrene 
• 536-89-0 m-tolylhydrazine 
• 93-58-3 benzoic acid methyl ester 
• 108-38-3 m-xylene 
• 6919-61-5 N-methoxy-N-methylbenzamide 
• 591-17-3 meta-bromotoluene 
• 98-86-2 acetophenone 
• 1428905-30-9 C₁₀H₁₂O 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 620-23-5 m-tolyl aldehyde 
• 611-73-4 Benzoylformic acid 
• 108-67-8 1,3,5-trimethyl-benzene 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 197245-87-7 (2,4,6-trimethylphenyl)(3’-methylphenyl)iodonium triflate 

Downstream Products

• 1283117-19-0 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-phenyl-5-m-tolyl-3,4-dihydropyrimidin-2(1H)-one 
• 40103-79-5 1-(3-methylphenyl)-2-phenyl-1,2-ethanedione 
• 19419-02-4 8-methyl-3-phenylcinnoline 
• 10501-72-1 6-methyl-3-phenylcinnoline 

Relevant articles and documents

Benzylic Aroylation of Toluenes Mediated by a LiN(SiMe3)2/Cs+System

Chemoselective deprotonative functionalization of benzylic C-H bonds is challenging, because the arene ring contains multiple aromatic C(sp2)-H bonds, which can be competitively deprotonated and lead to selectivity issues. Recently it was found that bimetallic [MN(SiMe3)2 M = Li, Na]/Cs+ combinations exhibit excellent benzylic selectivity. Herein, is reported the first deprotonative addition of toluenes to Weinreb amides mediated by LiN(SiMe3)2/CsF for the synthesis of a diverse array of 2-arylacetophenones. Surprisingly, simple methyl benzoates also react with toluenes under similar conditions to form 2-arylacetophenones without double addition to give tertiary alcohol products. This finding greatly increases the practicality and impact of this chemistry. Some challenging substrates with respect to benzylic deprotonations, such as fluoro and methoxy substituted toluenes, are selectively transformed to 2-aryl acetophenones. The value of benzylic deprotonation of 3-fluorotoluene is demonstrated by the synthesis of a key intermediate in the preparation of Polmacoxib.

Aerobic oxygenation of α-methylene ketones under visible-light catalysed by a CeNi3complex with a macrocyclic tris(salen)-ligand

A hetero-tetranuclear CeNi3 complex with a macrocyclic ligand catalysed the aerobic oxygenation of a methylene group adjacent to a carbonyl group under visible-light radiation to produce the corresponding α-diketones. The visible-light induced homolysis of the Ce-O bond of a bis(enolate) intermediate is proposed prior to aerobic oxygenation.

Ruthenium(II)-Catalyzed Cross-Coupling of Benzoyl Formic Acids with Toluenes: Synthesis of 2-Phenylacetophenones

Herein, we report a direct method to synthesize 2-phenylacetophenone through a ruthenium(II)-catalyzed cross-coupling reaction between acyl and benzyl radical. The various derivatives of 2-phenylacetophenone were prepared easily in moderate to good yields. These reactions provide a straightforward pathway to synthesize a variety of ketones bearing various functional groups.