59099-58-0

Basic information

• Product Name: Methanesulfonic acid, trifluoro-, 2-methoxyphenyl ester
• Synonyms: Methanesulfonic acid,trifluoro-,2-methoxyphenyl ester;trifluoromethanesulfonic acid 2-methoxyphenyl ester;o-anisyl trifluoromethanesulfonate;2-methoxyphenyltrifluoromethanesulfonate;2-methoxyphenyl 1-trifluoromethanesulfonate;o-anisyl triflate;2-methoxyphenyl triflate
• CAS NO: 59099-58-0
• Molecular Formula: C8H7F3O4S
• Molecular Weight: 256.202
• Mol File: 59099-58-0.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 116°C/17mmHg(lit.)
• Refractive Index: 1.4540 to 1.4580
• CAS DataBase Reference: Methanesulfonic acid, trifluoro-, 2-methoxyphenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Methanesulfonic acid, trifluoro-, 2-methoxyphenyl ester(59099-58-0)
• EPA Substance Registry System: Methanesulfonic acid, trifluoro-, 2-methoxyphenyl ester(59099-58-0)

Safety Data

• Hazardous Substances Data: 59099-58-0(Hazardous Substances Data)

Usage

General Description

Methanesulfonic acid, trifluoro-, 2-methoxyphenyl ester is a chemical compound that belongs to the class of organic compounds known as trifluoromethanesulfonates. It is commonly used as a reagent in organic synthesis, particularly in the production of pharmaceuticals and agrochemicals. Methanesulfonic acid, trifluoro-, 2-methoxyphenyl ester is highly reactive and can serve as a strong acid catalyst in various chemical reactions. It is also used as a solvent in electrochemical applications and as an electrolyte additive in lithium-ion batteries. Additionally, it may have potential uses in the field of industrial and electronic materials. However, it is important to handle this compound with care due to its corrosive and toxic nature.

Upstream product

• 109-72-8 n-butyllithium 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 492-95-5 2-methoxyphenyldiazonium tetrafluoroborate 
• 335-05-7 Trifluoromethanesulfonyl fluoride 
• 90-05-1 2-methoxy-phenol 
• 612-16-8 (2-methoxyphenyl)methanol 
• 1493-13-6 trifluorormethanesulfonic acid 
• 4416-67-5 2-tosyloxyanisole 
• 98910-57-7 2-methoxyphenyl mesylate 
• 100-02-7 4-nitro-phenol 
• 621-59-0 isovanillin 
• 17763-80-3 para-nitrophenyl triflate 

Downstream Products

• 839721-39-0 1-(1-Butoxy-vinyl)-2-methoxy-benzene 
• 190788-60-4 pinacol 2-anisylboronate 
• 86-26-0 2-methoxy-1,1'-biphenyl 
• 50798-94-2 N-benzyl-2-methoxyaniline 
• 1057402-38-6 C₁₉H₃₀O₈ 
• 321-28-8 1-fluoro-2-methoxybenzene 
• 15286-17-6 diethyl [2-(methoxy)phenyl]phosphonate 
• 1413281-94-3 C₂₂H₃₀F₃NO₇S*ClH 
• 92862-65-2 (E)-1-(2-methoxyphenyl)cyclohept-1-en 
• 500585-18-2 1-(o-anisyl)cyclooctene 
• 39877-86-6 1-(1-cyclopentenyl)-2-methoxy-benzene 
• 185347-49-3 α-(o-anisyl)-γ-butyrolactone 
• 1443013-44-2 (S)-α-(o-anisyl)-γ-butyrolactone 
• 1443013-75-9 (αS,βS)-α-(o-anisyl)-β-benzyloxymethyl-γ-butyrolactone 

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.

Dynamic Kinetic Cross-Electrophile Arylation of Benzyl Alcohols by Nickel Catalysis

Catalytic transformation of alcohols via metal-catalyzed cross-coupling reactions is very important, but it typically relies on a multistep procedure. We here report a dynamic kinetic cross-coupling approach for the direct functionalization of alcohols. The feasibility of this strategy is demonstrated by a nickel-catalyzed cross-electrophile arylation reaction of benzyl alcohols with (hetero)aryl electrophiles. The reaction proceeds with a broad substrate scope of both coupling partners. The electron-rich, electron-poor, and ortho-/meta-/para-substituted (hetero)aryl electrophiles (e.g., Ar-OTf, Ar-I, Ar-Br, and inert Ar-Cl) all coupled well. Most of the functionalities, including aldehyde, ketone, amide, ester, nitrile, sulfone, furan, thiophene, benzothiophene, pyridine, quinolone, Ar-SiMe3, Ar-Bpin, and Ar-SnBu3, were tolerated. The dynamic nature of this method enables the direct arylation of benzylic alcohol in the presence of various nucleophilic groups, including nonactivated primary/secondary/tertiary alcohols, phenols, and free indoles. It thus offers a robust alternative to existing methods for the precise construction of diarylmethanes. The synthetic utility of the method was demonstrated by a concise synthesis of biologically active molecules and by its application to peptide modification and conjugation. Preliminary mechanistic studies revealed that the reaction of in situ formed benzyl oxalates with nickel, possibly via a radical process, is an initial step in the reaction with aryl electrophiles.

Barbier–Negishi Coupling of Secondary Alkyl Bromides with Aryl and Alkenyl Triflates and Nonaflates

A mild and practical Barbier–Negishi coupling of secondary alkyl bromides with aryl and alkenyl triflates and nonaflates has been developed. This challenging reaction was enabled by the use of a very bulky imidazole-based phosphine ligand, which resulted in good yields as well as good chemo- and site selectivities for a broad range of substrates at room temperature and under non-aqueous conditions. This reaction was extended to primary alkyl bromides by using an analogous pyrazole-based ligand.