105728-75-4

Basic information

• Product Name: Methanone, [4-(dimethylamino)phenyl]-2-thienyl-
• CAS NO: 105728-75-4
• Molecular Formula: C13H13NOS
• Molecular Weight: 231.318
• Mol File: 105728-75-4.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Methanone, [4-(dimethylamino)phenyl]-2-thienyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Methanone, [4-(dimethylamino)phenyl]-2-thienyl-(105728-75-4)
• EPA Substance Registry System: Methanone, [4-(dimethylamino)phenyl]-2-thienyl-(105728-75-4)

Safety Data

• Hazardous Substances Data: 105728-75-4(Hazardous Substances Data)

Upstream product

• 579-49-7 2-(4-fluorobenzoyl)thiophene 
• 80-70-6 N,N,N',N'-tetramethylguanidine 
• 30717-57-8 N, N-dimethylthiophene-2-carboxamide 
• 24167-52-0 N,N-dimethyl-3-chlorobenzamide 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 88372-95-6 thiophen-2-yl(trimethylsilyl)methanone 
• 121-69-7 N,N-dimethyl-aniline 
• 105728-67-4 2-<4-(Dimethylamino)phenyl>-2-(2-thienyl)-1,3-dithian 
• 100-10-7 4-dimethylamino-benzaldehyde 

Relevant articles and documents

The Halogen–Samarium Exchange Reaction: Synthetic Applications and Kinetics

Fast I/Sm and Br/Sm exchanges take place when various aromatic or heterocyclic iodides and bromides are treated with nBu2SmCl?4 LiCl and nBu3Sm?5 LiCl, respectively. The resulting organosamarium reagents were efficiently quenched with aldehydes, ketones, and imines. Also, they undergo acylations when treated with N,N-dimethylamides leading to ketones. The rate of the Br/Sm exchange for a typical aryl bromide was determined and found to be 8.5×105 faster than the Br/Mg exchange, indicating that the rate of a metal-exchange is related to the ionic character of the carbon–metal bond and to the metal electronegativity.

Magnesium salt promoted tandem nucleophilic addition-Oppenauer oxidation of aldehydes with organozinc reagents

A magnesium salt promoted synthesis of ketones via tandem nucleophilic addition-Oppenauer oxidation of aldehydes using organozinc chemistry was demonstrated. Magnesium salts concomitantly generated via magnesium metal mediated organohalide zincation exhibit high efficacy for nucleophilic addition of organozinc reagents to aromatic aldehydes and thereafter Oppenauer oxidation whereby ketones are formed in high to excellent yields.

Reversed-polarity synthesis of Diaryl Ketones through palladium-catalyzed direct Arylation of 2-Aryl-1,3-dithianes

An umpolung approach to the synthesis of diaryl ketones has been developed based on in situ generation of acyl anion equivalents and their catalytic arylation. This method entails the base-promoted, palladium-catalyzed direct C-H arylation of 2- aryl-1,3-dithianes with aryl bromides. Use of MNACHTUNGTRENUNG( SiMe3)2 (M=Li, Na) base results in reversible deprotonation of the weakly acidic dithiane. In the presence of a Pd(NiXantphos)-based catalyst and aryl bromide, cross-coupling of the metallated 2-aryl- 1,3-dithiane takes place under mild conditions (2 h at rt) with yields as high as 96%. The resulting 2,2- diaryl-1,3-dithianes were converted into diaryl ketones by either molecular iodine, N-bromo succinimide (NBS) or Selectfluor in the presence of water. The dithiane arylation/hydrolysis can be performed in a one-pot procedure to yield a variety of diaryl ketones in good to excellent yields. This method is suitable for rapid and large-scale synthesis of diaryl ketones. A one-pot preparation of anti-cholesterol drug fenofibrate (TriCor) has been achieved on 10.0 mmol scale in 86% yield.