Trimethyl Orthoacetate from TCI (product code O0115) is an orthoester of acetic acid in which three methoxy groups are attached to a single carbon atom. Like its ethyl analogue, it is a versatile reagent in organic synthesis. It is best known for the Johnson–Claisen rearrangement, which converts allylic alcohols into γ,δ-unsaturated methyl esters. Laboratories also use trimethyl orthoacetate to build heterocycles, to form cyclic orthoesters that protect diols, as a mild methylating agent, and as a water scavenger in reactions that must stay dry. It is listed as a non-heterocyclic building block.
Researchers choose trimethyl orthoacetate when they want a methyl ester as the product, or when they want lighter by-products. It releases methanol and methyl acetate, which evaporate easily. Under acidic conditions the orthoester forms a reactive oxocarbenium intermediate. This makes it effective for closing benzimidazole, oxazoline and other methyl-substituted heterocyclic rings. The small size of the methoxy groups can also affect reaction rate and make purification easier. Because it reacts quickly with water, it helps keep a reaction free of moisture without extra solid drying agents.
In Indonesia, trimethyl orthoacetate is used by university organic chemistry laboratories, pharmaceutical and fine-chemical research groups, and research institutes working on synthetic methods. Common uses include making ester intermediates, preparing heterocyclic scaffolds for medicinal chemistry, and teaching or research work on sigmatropic rearrangements. AMI Scientific supplies the TCI grade so these laboratories can get a consistent reagent from a recognised brand for routine synthesis and method development.
Related TCI products
- Johnson–Claisen rearrangement: the reagent reacts with allylic alcohols to give γ,δ-unsaturated methyl esters directly, which makes it a standard choice when a methyl ester product is needed.
- Heterocycle formation: under acidic conditions it forms an oxocarbenium intermediate that closes rings efficiently, so it is useful for building methyl-substituted benzimidazoles, oxazolines and related heterocycles.
- Diol protection: it forms cyclic orthoesters with diols, giving chemists a way to protect hydroxyl groups temporarily during multi-step synthesis and remove the protection later under mild conditions.
- Mild methylation: its three methoxy groups let it act as a gentle methylating reagent where harsher alkylating agents would be unsuitable or would cause unwanted side reactions.
- Water scavenging: it reacts quickly with moisture to form volatile methanol and methyl acetate, so it keeps sensitive reactions dry without solid desiccants that would need to be filtered off.
| Brand | TCI (product code O0115) |
|---|---|
| CAS number | 1445-45-0 |
| Molecular formula | — |
| Purity | — |
| Category | Chemistry > Building Blocks > Non-Heterocyclic Building Blocks |
| Pack sizes | see the pack options listed on the product page |
| Physical form | liquid |
| Storage | keep tightly sealed, protected from moisture, in a cool and well-ventilated place |
Trimethyl orthoacetate reacts readily with water, so keep it in its original tightly closed container. Protect it from humidity and air, and ideally store it under dry inert gas once the container has been opened. Store it in a cool, dry, well-ventilated area, away from heat, sparks, open flames, acids and oxidising agents, because it is a flammable organic liquid. Handle it in a fume hood and wear chemical-resistant gloves, safety glasses and a lab coat. Use dry glassware and syringes when dispensing it. Always check the supplier's Safety Data Sheet for full hazard and disposal information before use.
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