TCI M1305, CAS 78440-76-3, is 3-Methoxymethylindole, an indole derivative carrying a methoxymethyl group at the 3-position. The compound is known as a synthetic reagent that serves as a source of the indol-3-ylmethyl unit, a fragment that is highly useful for attaching an indole framework onto target nucleophiles. In the organic chemistry laboratory, this material is a practical alternative to classical reagents such as gramine, because the methoxy group acts as a leaving group that can be substituted under controlled conditions, so alkylation proceeds more cleanly and is easier to manage.
The property that makes this reagent a preferred choice is the characteristic reactivity of the third position of the electron-rich indole ring. Under mild acidic or thermal conditions, the methoxy group can be released to form an electrophilic indol-3-ylmethyl intermediate, which is immediately captured by nucleophiles such as active methylene compounds, thiols, amines, or enolates. This pathway allows carbon-carbon as well as carbon-heteroatom bond formation to proceed efficiently without requiring benzylic halides, which tend to be unstable. The simple structure and moderate molecular weight also make product purification and reaction monitoring by chromatography more straightforward.
In Indonesian laboratories, TCI M1305 is typically used in university and institutional organic synthesis groups working on indole chemistry, in medicinal chemistry programmes that build tryptamine- and tryptophan-related frameworks, and in research units preparing intermediates for natural product studies. Because the reagent is a TCI-brand fine chemical intended for research use, it is generally handled in small quantities on the bench scale, stored in the laboratory chemical cabinet, and dispensed as needed for individual synthetic steps rather than bulk production.
Related TCI products
- Indol-3-ylmethylation of active methylene compounds: the reagent releases an electrophilic indol-3-ylmethyl intermediate that is captured directly by the enolizable carbon, forming the new bond cleanly.
- Synthesis of tryptamine- and tryptophan-related frameworks: attaching the indol-3-ylmethyl fragment to amine or amino acid derived nucleophiles builds the core skeleton needed for further medicinal chemistry work.
- Carbon-heteroatom bond formation with thiols and amines: the methoxy leaving group allows substitution under controlled mild acidic or thermal conditions without resorting to unstable benzylic halides.
- Replacement for gramine in alkylation protocols: chemists select this reagent when they want the same indol-3-ylmethyl transfer but with a more manageable and tidier reaction profile.
- Preparation of indole-containing intermediates for natural product studies: the simple structure and moderate molecular weight simplify purification and let reactions be followed easily by chromatography.
| Brand | TCI (Tokyo Chemical Industry) |
|---|---|
| CAS number | 78440-76-3 |
| Molecular formula | — |
| Purity | — |
| Category | Chemistry > Building Blocks > Heterocyclic Building Blocks |
| Pack sizes | available in standard TCI research-scale packaging; please confirm the available size when ordering |
| Physical form | — |
| Storage | keep in a tightly closed original container in a cool, dry place away from light, acids, and heat sources |
- Chemical name: 3-Methoxymethylindole
Store the container tightly closed in a cool, dry, well-ventilated area, away from direct sunlight, heat sources, and acidic vapours, since mild acid or elevated temperature can trigger loss of the methoxy group. Keep the material in its original TCI container or in a clean, chemically compatible amber glass bottle with a secure closure, and label any transferred portion clearly. Handle the compound inside a fume hood while wearing a laboratory coat, safety goggles, and suitable chemical-resistant gloves. Avoid inhaling dust and avoid skin or eye contact. Weigh and dispense only the quantity required for the reaction, close the container promptly to limit moisture uptake, and dispose of residues and contaminated materials as chemical waste according to institutional laboratory procedures.
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