Synlett 2012; 23(14): 2142-2143
DOI: 10.1055/s-0032-1317162
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© Georg Thieme Verlag Stuttgart · New York

Tetrabutylammonium Hydrogen Sulfate

Aditya Bhattacharyya
Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India, eMail: aditya8000@gmail.com
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Publikationsverlauf

Publikationsdatum:
09. August 2012 (online)

Introduction

Tetrabutylammonium hydrogen sulfate (TBAHS, 1), is a stable, hygroscopic, white solid (mp 169–171 °C). It is widely used in various fields of chemistry as phase-transfer catalyst (PTC) and ion-pairing reagent as mobile phase additive in HPLC. It has been also used in a variety of organic transformations some of which include the syntheses of triarylpyridines,[ 1 ] N-monosubstituted α-keto amides,[ 2 ] cyclic and acyclic β-disubstituted, α,β-unsaturated ketones,[ 3 ] 3-alkylated indoles,[ 4 ] benzopyran-annulated pyrano[2,3-c]pyrazoles,[ 5 ] N1-alkylated 3,4-dihydropyrimidine-2(1H)-ones,[ 6 ] 2-O-deacetylated glucosyl hydroxamates,[ 7 ] 1,2,3-triazoles,[ 8 ] 1,8-dioxooctahydroxanthenes,[ 9 ] β- and γ-amino ethers, morpholines and their higher homologues,[ 10 ] etc.

Although TBAHS is commercially available and inexpensive, it can be prepared from tetrabutylammonium azide[ 11 ] by treating it with potassium hydrogen sulfate and 10% aqueous sulfuric acid in aqueous medium (Scheme [1], eq. 1) or from tetrabutylammonium thiocyanate[ 12 ] by treating it with relatively concentrated sulfuric acid (70%) at 75 °C (Scheme [1], eq. 2).

Zoom Image
Scheme 1 Synthesis of tetrabutylammonium hydrogen sulfate (TBAHS, 1)
 
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