Phenoxyacetic Anhydride from TCI is a carboxylic acid anhydride made from two molecules of phenoxyacetic acid. In the laboratory it works as an acylating reagent that transfers the phenoxyacetyl group to nucleophiles such as amines and alcohols. Its best-known role is in oligonucleotide synthesis. There, the phenoxyacetyl group serves as an easily removable protecting group, and phenoxyacetic anhydride is used as a capping reagent in synthesis strategies that rely on milder deprotection conditions. It is catalogued as a non-heterocyclic building block for synthetic organic chemistry.
Chemists choose phenoxyacetic anhydride because it acylates well but is generally milder than the corresponding acid chloride. This makes reactions easier to control, and it does not release hydrogen chloride as a by-product. Instead, the by-product is phenoxyacetic acid, which is relatively easy to separate from the reaction mixture. The phenoxyacetyl group it introduces can be removed under milder basic conditions than certain simple acyl groups. This is especially valuable when working with sensitive molecules that cannot tolerate harsh deprotection. Like other anhydrides, however, this material is sensitive to moisture and must be handled with that in mind.
In Indonesia, phenoxyacetic anhydride is relevant to molecular biology, biotechnology and synthetic chemistry laboratories at universities, research institutes and industry. Research groups that synthesise or modify oligonucleotides can use it as a capping reagent under milder deprotection protocols. Organic chemistry groups can use it to introduce a removable phenoxyacetyl protecting group onto amines and alcohols. Teaching and research laboratories studying acylation chemistry may also find it a convenient, controllable alternative to more aggressive acid chloride reagents.
- Oligonucleotide synthesis capping: phenoxyacetic anhydride is used as a capping reagent in synthesis strategies built around milder deprotection conditions, which helps keep sensitive nucleotide products intact.
- Protection of amines: it transfers the phenoxyacetyl group to amine nucleophiles, giving a protecting group that can later be removed under comparatively mild basic conditions.
- Protection of alcohols: hydroxyl groups can be acylated with the phenoxyacetyl group, which is useful when a temporary, easily removable protecting group is needed during multistep synthesis.
- Controlled acylation reactions: because it is generally milder than the acid chloride, it gives more controllable acylation and avoids hydrogen chloride as a by-product in acid-sensitive systems.
- Work with sensitive molecules: the mild removal of the phenoxyacetyl group makes this reagent useful when substrates cannot survive the harsher conditions needed to remove some simple acyl groups.
| Brand | TCI (product code P0111) |
|---|---|
| CAS number | 14316-61-1 |
| Molecular formula | — |
| Purity | — |
| Category | Chemistry > Building Blocks > Non-Heterocyclic Building Blocks |
| Pack sizes | as listed in the TCI catalogue for product P0111 |
| Physical form | see the TCI product documentation and certificate of analysis |
| Storage | moisture-sensitive anhydride; keep tightly closed and protected from humidity |
Phenoxyacetic anhydride is a moisture-sensitive acid anhydride, so keep it in its original, tightly sealed container and store it in a cool, dry place away from humidity. Because Indonesia's climate is humid, extra protection such as a desiccator or storage under dry inert gas is recommended once the container has been opened. Keep it away from water, alcohols, amines and strong bases unless you are using it in a planned reaction. Weigh and transfer it quickly with dry glassware, and reseal the container immediately after use. Handle it in a fume hood while wearing suitable gloves, safety glasses and a lab coat. Always check the TCI safety data sheet for specific hazard, storage and disposal guidance.
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