901741

Sigma-Aldrich

Bis(triphenyl-λ5-phosphanylidene)ammonium hydrogendifluoride

greener alternative
Synonym(s):
PNP+[FHF]-, Bifluoride salt SuFEx catalyst, Triphenyl((triphenyl-phosphaneylidene)amino)phosphonium fluoride hydrofluoride, [Ph3P=N-PPh3]+[HF2]-
Empirical Formula (Hill Notation):
C36H31F2NP2
CAS Number:
Molecular Weight:
577.58

assay

≥95%

form

solid

reaction suitability

reagent type: catalyst

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

greener alternative category

Aligned

storage temp.

2-8°C

General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

Application

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.

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

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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