86364-02-5

Basic information

• Product Name: Methanesulfonic acid, trifluoro-, 2,6-dimethylphenyl ester
• Synonyms: 2,6-dimethylphenyl trifluoromethanesulphonate;2,6-dimethylphenyl trifluoromethanesulfonate;2,5-dimethylphenyl triflate;Methanesulfonic acid,trifluoro-,2,6-dimethylphenyl ester;2,6-dimethylphenyl triflate;2,6-dimethylphenyltrifluoromethylsulfonate
• CAS NO: 86364-02-5
• Molecular Formula: C9H9F3O3S
• Molecular Weight: 254.23
• Mol File: 86364-02-5.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: Methanesulfonic acid, trifluoro-, 2,6-dimethylphenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Methanesulfonic acid, trifluoro-, 2,6-dimethylphenyl ester(86364-02-5)
• EPA Substance Registry System: Methanesulfonic acid, trifluoro-, 2,6-dimethylphenyl ester(86364-02-5)

Safety Data

• Hazardous Substances Data: 86364-02-5(Hazardous Substances Data)

Upstream product

• 576-26-1 2.6-dimethylphenol 
• 1493-13-6 trifluorormethanesulfonic acid 
• 100379-00-8 2,6-dimethylbenzene boronic acid 
• 2926-30-9 sodium triflate 
• 108-48-5 2,6-dimethylpyridine 
• 17763-80-3 para-nitrophenyl triflate 
• 358-23-6 trifluoromethylsulfonic anhydride 

Downstream Products

• 325141-72-8 2-(2,6-bismethylphenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane 
• 1123-56-4 2,6-dimethylbenzaldehyde 
• 1139-60-2 2,6-dimethylbenzophenone 
• 14411-75-7 2-isopropyl-1,3-dimethylbenzene 
• 17059-45-9 1,3-dimethyl-2-propylbenzene 
• 632-46-2 2,6-dimethylbenzoic acid 
• 1425783-63-6 2-phenoxyethyl (2,6-dimethylphenyl)carbamate 
• 118604-67-4 S-2,6-dimethyl-N-(2-methoxy-1-methylethyl)-aniline 
• 441003-36-7 1-(2,6-dimethylphenyl)-3-methyl-1-butyn-3-ol 
• 28122-29-4 2,6-dimethyldiphenylmethane 
• 14920-81-1 methyl 2,6-dimethylbenzoate 
• 6575-13-9 2,6-dimethylbenzonitrile 
• 576-26-1 2.6-dimethylphenol 
• 39604-15-4 2,6-dimethylphenyl diethyl phosphate 

Relevant articles and documents

Ni-Catalyzed Cross-Electrophile Coupling of Aryl Triflates with Thiocarbonates via C-O/C-O Bond Cleavage

A nickel-catalyzed reductive coupling of aryl triflates with thiocarbonates is reported here. Both electron-rich and -deficient aryl C(sp2)-O electrophiles as well as a class of O-tBu S-alkyl thiocarbonates are compatible with the optimized reaction conditions, as evidenced by 49 examples. The reaction also proceeds with good chemoselective cleavage of the C-O bond with regard to thioesters. This work broadens the scope of nickel-catalyzed reductive cross-electrophile coupling reactions.

Bismuth-Catalyzed Oxidative Coupling of Arylboronic Acids with Triflate and Nonaflate Salts

Herein we present a Bi-catalyzed cross-coupling of arylboronic acids with perfluoroalkyl sulfonate salts based on a Bi(III)/Bi(V) redox cycle. An electron-deficient sulfone ligand proved to be key for the successful implementation of this protocol, which allows the unusual construction of C(sp2)-O bonds using commercially available NaOTf and KONf as coupling partners. Preliminary mechanistic studies as well as theoretical investigations reveal the intermediacy of a highly electrophilic Bi(V) species, which rapidly eliminates phenyl triflate.

Palladium nanoparticles: Chemoselective control for reductive Heck with aryl triflates and 2,3-dihydrofuran

The reductive-Heck reaction offers a unique entry to formal Csp2-Csp3 cross-coupling reactions that proceed in the absence of a main group organometallic coupling partner. Consequently, further development of new variants would be transformative. Unfortunately, controlling the relative rates of the organopalladium intermediates has proven difficult with homogenous, single-site Pd catalysts. This work describes a selective reductive Heck reaction catalyzed by Pd-nanoparticles. The reaction works well with electron-deficient aryl triflates at room temperature in the absence of ligands. This work addresses some of the challenges found in the reductive-Heck literature.