5697-42-7

Basic information

• Product Name: Sulfonium, dimethyl[2-(4-nitrophenyl)-2-oxoethyl]-, bromide
• CAS NO: 5697-42-7
• Molecular Formula: C10H12NO3S.Br
• Molecular Weight: 306.18
• Mol File: 5697-42-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Sulfonium, dimethyl[2-(4-nitrophenyl)-2-oxoethyl]-, bromide(CAS DataBase Reference)
• NIST Chemistry Reference: Sulfonium, dimethyl[2-(4-nitrophenyl)-2-oxoethyl]-, bromide(5697-42-7)
• EPA Substance Registry System: Sulfonium, dimethyl[2-(4-nitrophenyl)-2-oxoethyl]-, bromide(5697-42-7)

Safety Data

• Hazardous Substances Data: 5697-42-7(Hazardous Substances Data)

Upstream product

• 75-18-3 dimethylsulfide 
• 99-81-0 4-Nitrophenacyl bromide 

Downstream Products

• 13573-34-7 4-(4-nitrophenyl)-2,6-bisphenylpyrimidine 
• 2126-08-1 (4-nitrophenyl)(3-phenyl-4,5-dihydroisoxazol-5-yl)methanone 
• 93944-58-2 benzofuran-2-yl(4-nitrophenyl)methanone 
• 1361406-72-5 C₂₁H₁₉NO₅S 
• 7380-84-9 2-(dimethyl-λ⁴-sulfanylidene)-1-(4-nitrophenyl)ethan-1-one 

Relevant articles and documents

Synthesis of functionalized thietanes via electrophilic carbenoid-induced ring expansion of thiiranes with sulfonium acylmethylides as carbene precursors

Various functionalized thietanes were prepared from thiiranes via an electrophilic ring expansion with rhodium carbenoids as electrophiles generated from safe and readily accessible dimethylsulfonium acylmethylides. The reaction appears to proceed through electrophilic metallocarbenoid-induced activation of thiiranes, nucleophilic ring-opening of the activated thiiranes with dimethyl sulfide as a transient nucleophile, and nucleophilically intramolecular cyclization. The Umpolung from the nucleophilic ylides to the electrophilic carbenoids plays an important role in both the activation and ring opening of thiiranes and subsequent cyclization. The current method provides a new strategy for the efficient preparation of functionalized thietanes from readily available thiiranes.

Functionalized α-keto stabilized sulfonium ylides as highly active ligand precursors for palladium catalyzed Suzuki-Miyaura cross-couplings

Five α-keto stabilized sulfonium ylides as type (Me) 2SCHC(O)C6H4-p-X (X = H, Br, NO2, CH3 and OCH3) {L1-L5} were used as ligand precursors in the Suzuki-Miyaura cross-coupling reaction. The best catalytic performance was obtained by using a sulfonium ylide/Pd ratio of 2:1. The catalytic systems displayed high activities, which increased in the order R = NO2 (L3) 2) 1) 3 (L4) 3 (L5). The coupling reactions proceeded smoothly with 0.05 mol% PdCl2 and 0.1 mol% L5 in DMF at 130 °C between varieties of electronically activated, deactivated and neutral aryl halides and aryl boronic acids within short reaction times and without the need for exclusion of air which gave good to high yields of the corresponding products. All the studied ligands demonstrated very high activity in the Suzuki-Miyaura cross-coupling, which yielded turnover numbers up to 1940. Comparative studies showed that the performance of sulfonium ylide L5 is significantly superior to that of related phosphine-free ligands.

Synthesis of some new 2,4,6-trisubstituted phenyl pyrimidines using 4-nitro and 4-fluorophenacyldimethylsulfonium bromides with aromatic aldehydes

4-Nitrophenacyldimethylsulfonium bromide and 4- fluorophenacyldimethylsulfonium bromide have been prepared by the reaction of dimethyl sulfide with 4-substitutedphenacyl bromide in benzene at reflux temperature under nitrogen atmosphere. These sulfonium s