Pyrylium tetrafluoroborate is an unsubstituted pyrylium salt: an aromatic, six-membered, oxygen-containing ring cation paired with a tetrafluoroborate anion. TCI supplies it under product code P2823 in its heterocyclic building blocks category. Synthesis chemists know it as a highly reactive electrophile toward primary amines, which it converts into pyridinium salts. This reaction underpins several modern methods for turning amino groups into other functional groups. It is also a classic route to pyridinium derivatives and other heterocycles.
The reagent's main appeal is its selectivity for primary amino groups. That includes amines on heteroaromatic rings, which are usually difficult to activate. Once the amine becomes a pyridinium salt, the original nitrogen is a good leaving group. This opens the way to nucleophilic substitution under relatively mild conditions, for example to form halides or ethers. The approach is especially useful for late-stage modification of complex molecules, where harsh conditions could damage sensitive groups. The non-nucleophilic tetrafluoroborate anion also helps keep the pyrylium cation stable as a salt that can be handled.
In Indonesian laboratories, this compound suits university organic chemistry research groups, medicinal chemistry and pharmaceutical development teams, and institutions that work on heterocyclic synthesis. Researchers who need to convert amino groups or prepare pyridinium compounds can add it to their synthetic toolbox. Because it is a TCI product, laboratories get a consistently identified reagent that fits well into documented, reproducible procedures for academic research, method development and student training in advanced synthetic chemistry.
Advantages (TCI brochure)
- Activates the amino group of amino heteroaromatics, converting it to the leaving group.
- The resulting pyridinium salts can be applied to aromatic nucleophilic substitution under mild conditions without purification.
- Suitable for late-stage functionalization due to high functional-group tolerance.
TCI brochures (PDF)
- Pyrylium Salt for Nucleophilic Aromatic Substitution Reactions 2023-10-17 · p. 1
Related TCI products
- TCI T3968 448-61-3 2,4,6-Triphenylpyrylium Tetrafluoroborate
- TCI T2375 773-01-3 2,4,6-Trimethylpyrylium Tetrafluoroborate
- TCI C0905 63212-53-3 2-Chloro-3-ethylbenzoxazolium Tetrafluoroborate
- TCI T2648 429-42-5 Tetrabutylammonium Tetrafluoroborate
- TCI T2224 105832-38-0 N,N,N',N'-Tetramethyl-O-(N-succinimidyl)uronium Tetrafluoroborate
- TCI T2198 69444-47-9 Triethylmethylammonium Tetrafluoroborate
- Pyridinium salt formation from primary amines: the pyrylium cation reacts readily and selectively with primary amino groups, so it is a dependable way to prepare pyridinium salts.
- Deaminative functionalization: converting an amino group into a pyridinium leaving group lets chemists replace nitrogen with other functional groups using modern deamination strategies.
- Activation of heteroaromatic amines: the reagent can activate amines on heteroaromatic rings, which are usually hard to activate, so it widens the range of usable substrates.
- Nucleophilic substitution to form halides or ethers: the pyridinium intermediate acts as a good leaving group, so substitution can proceed under relatively mild conditions.
- Late-stage modification of complex molecules: its selectivity and mild reaction conditions suit medicinal chemistry projects where amino groups must be transformed without disturbing other sensitive functional groups.
From the TCI brochure
- Nucleophilic aromatic substitution of amino heteroaromatics
- Arylamination of amino heteroaromatics
- Deaminative chlorination of amino heteroaromatics
| Brand | TCI (product code P2823) |
|---|---|
| CAS number | 80279-50-1 |
| Molecular formula | — |
| Purity | — |
| Category | Chemistry > Building Blocks > Heterocyclic Building Blocks |
| Pack sizes | available in the pack sizes TCI offers for product P2823 |
| Physical form | pyrylium salt with a tetrafluoroborate counter-anion |
| Storage | keep in the original tightly closed container, as specified on the TCI label and Safety Data Sheet |
Data from the TCI brochure
| Kemasan | 1g |
|---|
Source: TCI brochure RR192 (2023-10-17)
Store pyrylium tetrafluoroborate in its original, tightly sealed TCI container in a cool, dry, well-ventilated chemical storage area, away from moisture, heat sources and incompatible substances such as strong bases and amines. Keep the label legible and record the date the container was opened. Handle the compound in a fume hood and wear appropriate personal protective equipment, including chemical-resistant gloves, safety glasses and a laboratory coat. Avoid creating dust, inhaling it, or letting it touch skin and eyes. Always check the TCI Safety Data Sheet for specific hazard, first-aid and disposal guidance before use, and dispose of residues according to institutional and local regulations.
References cited in the TCI brochure
- Daniel Moser. Selective Functionalization of Aminoheterocycles by a Pyrylium Salt Angewandte Chemie International Edition, 2018. doi:10.1002/anie.201806271
- Clément Ghiazza. Deaminative chlorination of aminoheterocycles Nature Chemistry, 2021. doi:10.1038/s41557-021-00812-0
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