Bis(triphenyl-λ5-phosphanylidene)ammonium hydrogendifluoride

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PNP+[FHF]-, Bifluoride salt SuFEx catalyst, Triphenyl((triphenyl-phosphaneylidene)amino)phosphonium fluoride hydrofluoride, [Ph3P=N-PPh3]+[HF2]-
Empirical Formula (Hill Notation):
CAS Number:
Molecular Weight:





reaction suitability

reagent type: catalyst

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General description

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Bifluoride salt reported by K. Barry Sharpless and colleagues as a catalyst for sulfur(VI) fluoride exchange (SuFEx)-based AA-BB polycondensation reactions to prepare polysulfonates with diverse structures, narrow polydispersity, and excellent thermal and hydrolytic stability. Bisalkylsulfonyl fluorides, the AA monomers, were prepared from ethenesulfonyl fluoride (746959) and amines/anilines while bisphenol bis(t-butyldimethylsilyl) ethers, the BB monomers, were synthesized using tert-butyldimethylsilyl chloride (190500) and bisphenols. Varying the amines, anilines, and bisphenols results in assorted polymeric backbones, including those bearing orthogonal side chains for modification post-polymerization (e.g. by CuAAC). Reaction is amenable to scale up.


NONH for all modes of transport

WGK Germany


Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Bing Gao et al.
Nature chemistry, 9(11), 1083-1088 (2017-10-25)
Polysulfates and polysulfonates possess exceptional mechanical properties making them potentially valuable engineering polymers. However, they have been little explored due to a lack of reliable synthetic access. Here we report bifluoride salts (Q
Hua Wang et al.
Angewandte Chemie (International ed. in English), 56(37), 11203-11208 (2017-08-10)
The SuFEx-based polycondensation between bisalkylsulfonyl fluorides (AA monomers) and bisphenol bis(t-butyldimethylsilyl) ethers (BB monomers) using [Ph
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The Sharpless Lab pursues useful new reactivity and general methods for selectively controlling chemical reactions.
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