68723-25-1

Basic information

• Product Name: (2-methylphenyl)-1-naphthylmethanone
• Synonyms: (2-methylphenyl)-1-naphthylmethanone
• CAS NO: 68723-25-1
• Molecular Weight: 246.309
• Mol File: 68723-25-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (2-methylphenyl)-1-naphthylmethanone(CAS DataBase Reference)
• NIST Chemistry Reference: (2-methylphenyl)-1-naphthylmethanone(68723-25-1)
• EPA Substance Registry System: (2-methylphenyl)-1-naphthylmethanone(68723-25-1)

Safety Data

• Hazardous Substances Data: 68723-25-1(Hazardous Substances Data)

Upstream product

• 91-20-3 naphthalene 
• 933-88-0 ortho-toluoyl chloride 
• 529-19-1 2-Methylbenzonitrile 
• 703-55-9 1-naphthylmagnesiumbromide 
• 7496-12-0 1-o-toluoyl-[2]naphthoic acid 
• 86785-12-8 3-methyl-2-[1]naphthoyl-benzoic acid 
• 932-31-0 ortho-tolylmagnesium bromide 
• 5343-99-7 1,2-naphthalenedicarboxylic anhydride 
• 4792-30-7 3-methylphthalic acid anhydride 
• 33872-80-9 o-tolyl magnesium chloride 
• 879-18-5 naphthalene-1-carbonic acid chloride 
• 86-53-3 1-Cyanonaphthalene 
• 68971-87-9 (2-tolyl)tributyltin 
• 20204-73-3 1-(2-methylbenzyl)naphthalene 

Downstream Products

• 56-55-3 benz[a]anthracene 
• 62784-64-9 1-naphthyl-2-(tolyl)methanol 
• 20204-73-3 1-(2-methylbenzyl)naphthalene 

Relevant articles and documents

Sterically Hindered Ketones via Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Amides by N-C(O) Activation

Herein, we report a new protocol for the synthesis of sterically hindered ketones that proceeds via palladium-catalyzed Suzuki-Miyaura cross-coupling of unconventional amide electrophiles by selective N-C(O) activation. Mechanistic studies demonstrate that steric bulk on the amide has a major impact, which is opposite to the traditional Suzuki-Miyaura cross-coupling of sterically hindered aryl halides. Structural and computational studies provide insight into ground-state distortion of sterically hindered amides and show that ortho-substitution alleviates the N-C(O) bond twist.

Selective synthetic routes to sterically hindered unsymmetrical diaryl ketones via arylstannanes

Bulky arylstannanes and bulky aroyl chlorides are good reaction partners for the synthesis of two-, three-, and even four-ortho-substituted benzophenones, in good to excellent isolated yields (47-91%). Three simple and direct routes, with differential advantages, are proposed: (i) a catalyst-free protocol, in o-dichlorobenzene (ODCB) at 180 °C; (ii) a room temperature protocol, using AlCl3 (0.5 equiv), in dichloromethane (DCM); and (iii) a solvent-free, indium-promoted procedure. A radical mechanism is proposed for the indium-mediated reactions.2011 American Chemical Society.

Palladium-phosphinous acid-catalyzed cross-coupling of aryl and acyl halides with aryl-, alkyl-, and vinylzinc reagents

(Chemical Equation Presented) Several palladium-phosphinous acids have been prepared and employed in cross-coupling reactions of aryl or acyl halides with aliphatic and aromatic organozinc reagents. The POPd7-catalyzed reaction of aryl halides, including electron-rich aryl chlorides, and arylzinc reagents was found to afford biaryls exhibiting alkoxy, alkylthio, amino, ketone, cyano, nitro, ester, and heteroaryl groups in 75-93% yield. Excellent results were obtained with sterically hindered substrates which gave di- and tri-ortho-substituted biaryls in up to 92% yield. Aryl halides also undergo POPd7-catalyzed aryl-vinyl and aryl-alkyl bond formation under mild conditions. Styrenes and alkylarenes were prepared in 79-93% yield from aryl halides and vinyl or alkylzinc reagents. The replacement of aryl halides by acyl halides provides access to ketones which were produced in up to 98% yield when POPd was used as catalyst. This approach overcomes the limited substrate scope, reduced regiocontrol, and low functional group tolerance of traditional Friedel-Crafts acylation methods.