87241-55-2

Basic information

• Product Name: Methanesulfonic acid, trifluoro-, 4-(1-oxopropyl)phenyl ester
• CAS NO: 87241-55-2
• Molecular Formula: C10H9F3O4S
• Molecular Weight: 282.24
• Mol File: 87241-55-2.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Methanesulfonic acid, trifluoro-, 4-(1-oxopropyl)phenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Methanesulfonic acid, trifluoro-, 4-(1-oxopropyl)phenyl ester(87241-55-2)
• EPA Substance Registry System: Methanesulfonic acid, trifluoro-, 4-(1-oxopropyl)phenyl ester(87241-55-2)

Safety Data

• Hazardous Substances Data: 87241-55-2(Hazardous Substances Data)

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 70-70-2 4-hydroxypropiophenone 
• 17763-67-6 Phenyl triflate 
• 108-95-2 phenol 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 66107-30-0 4-bromophenyl trifluoromethanesulfonate 
• 109586-39-2 4-iodophenyl trifluoromethanesulfonate 
• 123-62-6 propionic acid anhydride 

Downstream Products

• 17745-40-3 methyl p-propanoylbenzoate 
• 79219-21-9 1-butyl-4-propionylbenzene 
• 52129-98-3 4-propionylbenzonitrile 

Relevant articles and documents

Olefin Metathesis, p-Cresol, and the Second Generation Grubbs Catalyst: Fitting the Pieces

p-Cresol as additive to the Grubbs second generation catalyst (GII) allows the cross-metathesis of acrylates with prop-1-en-1-ylbenzenes under conditions that only give the prop-1-en-1-ylbenzene self-metathesis product in the absence of cresol. NMR and IR spectroscopy, MALDI-TOF MS and XPS supported the formation of a ruthenium benzylidene with hydrogen bonds between p-cresol and the chloride ligands of GII. XPS furthermore confirmed p-cresol to increase the binding energies of the GII Ru 3d5/2, 3d3/2, 3p3/2 and 3p1/2 photoelectron lines, whereas 1H NMR spectroscopy indicated the carbene carbon and hydrogen to be shielded. It is thus postulated that p-cresol allows for more facile interaction between electron-deficient compounds and the ruthenium benzylidene by decreasing the electron density on the metal center and increasing the electron density on the carbene.

Biaryl and aryl ketone synthesis via Pd-catalyzed decarboxylase coupling of carboxylate salts with aryl triflates

A bimetallic catalyst system has been developed that for the first time allows the decarboxylative crosscoupling of aryl and acyl carboxylates with aryl triflates. In contrast to aryl halides, these electrophiles give rise to non-coordinating anions as byproducts, which do not interfere with the decarboxylation step that leads to the generation of the carbon nucleophilic crosscoupling partner. As a result, the scope of carboxylate substrates usable in this transformation was extended from ortho-substituted or otherwise activated derivatives to a broad range of ortho-, meta-, and para-substituted aromatic carboxylates. Two alternative protocols have been optimized, one involving heating the substrates in the presence of CuI/1,10- phenanthroline (10-15 mol %) and PdI2/phosphine (23 mol%) in NMP for 1-24 h, the other involving CuI/l,10-phenanthroline (615mol%) and PdBr2/Tol-BINAP (2 mol % ) in NMP using microwave heating for 5-10 min. While most products are accessible using standard heating, the use of microwave irradiation was found to be beneficial especially for the conversion of non-activated carboxylates with functionalized aryl triflates. The synthetic utility of the transformation is demonstrated with 48 examples showing the scope and limitations of both protocols. In mechanistic studies, the special role of microwave irradiation is elucidated, and further perspectives of decarboxylase crosscouplings are discussed.

Aryl fluoroalkanesulfonate chemistry. A new approach to labelled arene elaboration

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