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901741

Sigma-Aldrich

Bis(triphenyl-λ5-phosphanylidene)ammonium hydrogendifluoride

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Synonym(s):

Bifluoride salt SuFEx catalyst, PNP+[FHF]-, Triphenyl((triphenyl-phosphaneylidene)amino)phosphonium fluoride hydrofluoride, [Ph3P=N-PPh3]+[HF2]-

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About This Item

Empirical Formula (Hill Notation):
C36H31F2NP2
CAS Number:
2055837-32-4
Molecular Weight:
577.58
UNSPSC Code:
12352101

Assay

≥95%

form

solid

reaction suitability

reagent type: catalyst

greener alternative product characteristics

Catalysis
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Aligned,

storage temp.

2-8°C

General description

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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.

Other Notes

1.SuFEx-Based Polysulfonate Formation from Ethenesulfonyl Fluoride–Amine Adducts

2.Bifluoride-catalysed sulfur(vi) fluoride exchange reaction for the synthesis of polysulfates and polysulfonates

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Description
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Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

901741-VAR:
901741-100MG:
901741-250MG:
901741-BULK:

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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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