36439-44-8

Basic information

• Product Name: tetramethylammonium phenoxide
• Synonyms: tetramethylammonium phenoxide
• CAS NO: 36439-44-8
• Molecular Weight: 167.251
• Mol File: 36439-44-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: tetramethylammonium phenoxide(CAS DataBase Reference)
• NIST Chemistry Reference: tetramethylammonium phenoxide(36439-44-8)
• EPA Substance Registry System: tetramethylammonium phenoxide(36439-44-8)

Safety Data

• Hazardous Substances Data: 36439-44-8(Hazardous Substances Data)

Upstream product

• 75-59-2 tetramethyl ammoniumhydroxide 
• 108-95-2 phenol 
• 115-86-6 phosphoric acid triphenyl ester 
• 373-68-2 tetramethylammonium fluoride 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 37397-35-6 tetramethyl-ammonium; ethylate 
• 122-79-2 Phenyl acetate 

Downstream Products

• 791-28-6 Triphenylphosphine oxide 
• 636-46-4 4-hydroxyisophthalic acid 
• 69-72-7 salicylic acid 
• 99-96-7 4-hydroxy-benzoic acid 
• 119-61-9 benzophenone 
• 5623-46-1 4-(4'-hydroxyphenyl)benzophenone 
• 114746-23-5 2-hydroxy-4'-benzoylbiphenyl 
• 91-22-5 quinoline 
• 40515-82-0 2-(2-quinolinyl)phenol 

Relevant articles and documents

Multiple Approaches to the in Situ Generation of Anhydrous Tetraalkylammonium Fluoride Salts for SNAr Fluorination Reactions

This article focuses on the development of practical approaches to the in situ generation of anhydrous fluoride salts for applications in nucleophilic aromatic substitution (SNAr) reactions. We report herein that a variety of combinations of inexpensive nucleophiles (e.g., tetraalkylammonium cyanide and phenoxide salts) and fluorine-containing electrophiles (e.g., acid fluoride, fluoroformate, benzenesulfonyl fluoride, and aryl fluorosulfonate derivatives) are effective for this transformation. Ultimately, we demonstrate that the combination of tetramethylammonium 2,6-dimethylphenoxide and sulfuryl fluoride (SO2F2) serves as a particularly practical route to anhydrous tetramethylammonium fluoride. This procedure is applied to the SNAr fluorination of a range of electron-deficient aryl and heteroaryl chlorides as well as nitroarenes.

C(sp3)-O bond-forming reductive elimination from PdIV with diverse oxygen nucleophiles

This article describes an investigation of C(sp3)-O bond-forming reductive elimination reactions from PdIV complexes. Phenoxide, acetate, difluoroacetate, dimethylphosphate, tosylate, and nitrate nucleophiles are shown to participate in this reaction. In all cases, C(sp3)-O bond formation occurs with high selectivity over potentially competing C(sp2)-O coupling. Additives have a profound impact on the chemoselectivity of these reductive elimination reactions. An excess of RO- was found to limit competing C(sp3)-C(sp2) bond-forming reductive elimination, while the presence of Lewis acidic cations was found to suppress competing C(sp3)-F coupling. Mechanistic investigations were conducted, and the available data are consistent with a sequence involving pre-equilibrium dissociation of the oxyanion ligand (RO-) followed by nucleophilic attack of RO- on a cationic PdIV-alkyl intermediate.

A dinuclear strontium(II) complex as substrate-selective catalyst of ester cleavage

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