One-Pot High-Yield Synthesis of a Tripodal Triamine Building Block in an Ammonia Ethanolic Solution
An improved, one-pot synthesis of tripodal triamine 1,1,1-tris(aminomethyl)ethane (<b>tame</b>), CH<sub>3</sub>C(CH<sub>2</sub>NH<sub>2</sub>)<sub>3</sub>, is reported, achieving a high yield of 70%. This method addresses the limitations of the existing low-yield (15%) route by systematically eliminating side reactions. The synthesis involves reacting 1,1,1-tris(bromomethyl)ethane, CH<sub>3</sub>C(CH<sub>2</sub>Br)<sub>3</sub>, with ammonia in ethanol at 150 °C, above the critical temperature of neat ammonia, for an extended period to suppress byproducts. The <b>tame</b>·3HBr salt is isolated via crystallization without column chromatography, yielding a SC-XRD quality material.
Authors
- Kazuma Takahara (ORCID: https://orcid.org/0009-0006-9141-8884)
- Høgni Weihe (ORCID: https://orcid.org/0000-0001-6194-1486)
- Jesper Bendix (ORCID: https://orcid.org/0000-0003-1255-2868)
Institutions
- University of Copenhagen (DK)
- Okayama University (JP)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-06-30
- DOI
- https://doi.org/10.1021/acs.joc.5c00474
- Primary Topic
- Metal-Organic Frameworks: Synthesis and Applications
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Iketani Science and Technology Foundation
- Novo Nordisk Fonden
- Japan Society for the Promotion of Science
- Japan Science and Technology Agency