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Description
TCI D4288 is N,N-Dimethyl-1,4-cyclohexanediamine supplied as a mixture of cis- and trans- isomers, a cyclic aliphatic diamine that serves as a non-heterocyclic building block in organic synthesis laboratories. The molecule is built on a cyclohexane framework carrying two amine groups at the 1- and 4-positions: one of these has been dimethylated and is therefore a tertiary amine, while the other remains a primary amine. This combination of two nitrogen centres at different levels of substitution is what makes the compound a versatile reagent for assembling larger molecular frameworks in a controlled manner.
The characteristic that makes this material a preferred choice is the difference in reactivity between the primary amine and the tertiary amine within a single molecule. The primary amine can be directed toward acylation, sulfonylation, reductive amination, urea formation, and nucleophilic aromatic substitution, while the dimethylamino group tends to act as a base, as a solubility-enhancing group, or as a coordination point for metals. The saturated cyclohexane framework provides conformational rigidity together with a relatively fixed distance between the two nitrogen atoms, a property that is useful when researchers want defined geometry rather than the flexibility of an open-chain diamine.
In Indonesian laboratories, this building block is typically used in university and institutional research groups working on medicinal chemistry, materials chemistry, and coordination chemistry, as well as in industrial R&D laboratories developing new molecular candidates. It is normally handled at bench scale for exploratory route development, where a small quantity of a well-defined difunctional reagent is enough to construct and screen a series of analogues. Because it is delivered as an isomer mixture, it is generally selected for work where the cis/trans ratio is not the deciding factor in the outcome.
Laboratory Applications
- Medicinal chemistry scaffold construction — the primary amine allows analogue libraries to be built by acylation or reductive amination while the dimethylamino group is retained as a basic solubilising handle.
- Amide and sulfonamide synthesis — the accessible primary amine reacts selectively with acyl chlorides, anhydrides, and sulfonyl chlorides, leaving the tertiary amine untouched under standard bench conditions.
- Urea and carbamate formation — reaction of the free primary amine with isocyanates or carbonyl equivalents gives rigid, conformationally defined linkers built on the saturated cyclohexane core.
- Nucleophilic aromatic substitution — the primary amine displaces activated halides on electron-poor aromatic rings, installing a basic side chain onto heteroaryl and aryl frameworks in a single step.
- Ligand preparation for coordination chemistry — the two nitrogen donors at fixed 1,4-spacing on a rigid ring make it a useful precursor for metal-binding ligands and complexation studies.
Specifications
- Brand: TCI (Tokyo Chemical Industry)
- CAS number: 42389-50-4
- Chemical name: N,N-Dimethyl-1,4-cyclohexanediamine (cis- and trans- mixture)
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Pack sizes: available in standard TCI research-scale catalogue packs; please confirm the currently offered size when ordering
- Storage note: keep tightly closed in a cool, dark place under the conditions stated on the manufacturer's label and Safety Data Sheet
Handling and Storage
Store the container tightly closed in a cool, dark, and well-ventilated place, following the storage conditions printed on the manufacturer's label and Safety Data Sheet. As an aliphatic amine, the material is best kept in its original tightly sealed container or in a compatible, clearly labelled glass container with a chemically resistant closure, and protected from moisture, air, and carbon dioxide, which can degrade amines over time. Keep it separated from acids, acyl halides, and strong oxidising agents. All handling, weighing, and transfers should be carried out in a fume hood using appropriate personal protective equipment, including chemical-resistant gloves, safety goggles, and a laboratory coat. Consult the current Safety Data Sheet before use and dispose of residues and contaminated materials through the laboratory's chemical waste procedure.
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