1276113-19-9

Usage

Chemical structure

A compound consisting of a trimethylsilylphenyl group attached to a nonafluorobutane-1-sulfonate group.

Usage

Commonly used as a reagent in organic synthesis, particularly in the fluorination of organic compounds.

Reactivity

Highly reactive and versatile, capable of selectively introducing fluorine atoms into various organic molecules.

Protecting group

The trimethylsilyl group can serve as a protecting group for alcohols and amines, making it a valuable tool in organic chemistry.

Stability

The nonafluorobutane-1-sulfonate group provides stability to the compound.

Solubility

The nonafluorobutane-1-sulfonate group enhances solubility in many organic solvents.

Utility

Highly useful in a wide range of chemical reactions due to its stability and solubility.

Upstream product

• 95-57-8 2-monochlorophenol 
• 17881-65-1 (2-chlorophenoxy)trimethylsilane 
• 375-72-4 Nonafluorobutanesulfonyl fluoride 
• 3376-24-7 N-tert-butyl-α-phenylnitrone 
• 18036-83-4 o-(trimethylsilyl)phenol trimethylsilyl ether 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 15288-53-6 o-(trimethylsilyl)phenol 
• 4466-24-4 2-Butylfuran 

Downstream Products

• 4706-43-8 1-benzyl-1H-benzotriazole 
• 4107-98-6 N,N-diisopropylaniline 
• 15288-53-6 o-(trimethylsilyl)phenol 
• 7115-18-6 methyl 2-(2-oxopropyl)benzoate 
• 23699-69-6 phenyl(2-(phenylamino)phenyl)methanone 
• 205642-01-9 9-(toluene-4-sulphonyl)-2,3,4,9-tetrahydro-1H-carbazole 
• 217-59-4 triphenylene 

Relevant academic research and scientific papers

2-(Trimethylsilyl)phenyl Trimethylsilyl Ethers as Stable and Readily Accessible Benzyne Precursors

Stable 2-(trimethylsilyl)phenyl trimethylsilyl ethers, readily obtained from the corresponding halogenated phenols in two steps, were identified as novel benzyne precursors. These species were converted to benzynes by a domino reaction of O-desilylation,

Continuous-flow synthesis of trimethylsilylphenyl perfluorosulfonate benzyne precursors

2-(Trimethylsilyl)phenyl perfluorosulfonated aryne precursors may now be accessed using flow chemistry, enabling the fast preparation of pure compounds with no requirement for low temperature lithiation or column chromatography. The process has been adapted to novel nonaflate precursors, utilizing the cheaper and more user-friendly nonaflyl fluoride reagent. The resultant nonaflates are shown to successfully participate in a range of aryne reaction classes.

A domino process for benzyne preparation: Dual activation of o-(trimethylsilyl)phenols by nonafluorobutanesulfonyl fluoride

Benzynes were generated from o-(trimethylsilyl)phenols using nonafluorobutanesulfonyl fluoride (NfF) by a domino process, i.e., the nonaflation of the phenolic hydroxyl group of o-(trimethylsilyl)phenols by NfF followed by the attack of the produced fluoride ion on the trimethylsilyl group. The generated benzyne immediately underwent various reactions to give polysubstituted benzenes.