Tricyclo[3.3.1.13,7]decane-1,3,5,7-tetramine
[CAS# 16004-77-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: Tricyclo[3.3.1.13,7]decane-1,3,5,7-tetramine
• Synonyms: adamantane-1,3,5,7-tetramine
• Molecular Formula: C₁₀H₂₀N₄
• Molecular Weight: 196.29
• CAS Registry Number: 16004-77-6
• SMILES: C1C2(CC3(CC1(CC(C2)(C3)N)N)N)N

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08 Danger
• Hazard Statements: H302-H314-H361-H412
• Precautionary Statements: P501-P273-P260-P270-P202-P201-P264-P280-P308+P313-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405
• Transport Information: UN 3259

Discovory and Applicatios

Tricyclo[3.3.1.1^3,7]decane-1,3,5,7-tetramine is a polycyclic tetraamine compound with a rigid cage-like structure. It belongs to the class of adamantane-like polyamines, characterized by a tricyclic hydrocarbon backbone in which four primary amine groups are symmetrically positioned at the bridgehead carbon atoms. The chemical structure is derived from the tricyclo[3.3.1.1^3,7]decane framework, a saturated hydrocarbon system that provides high molecular symmetry and steric stability.

The discovery of tricyclo[3.3.1.1^3,7]decane-1,3,5,7-tetramine is associated with research into cage compounds in the mid-20th century, during a period of active investigation into polycyclic hydrocarbons and their functionalized derivatives. This class of compounds gained attention for their unique geometric features and the possibility of exploiting their structural rigidity for applications in supramolecular chemistry, materials science, and ligand design. The synthesis of the parent tricyclic hydrocarbon structure typically involves cyclization reactions followed by functional group modifications to introduce amine substituents.

Tricyclo[3.3.1.1^3,7]decane-1,3,5,7-tetramine has been studied for its application in coordination chemistry, particularly as a multidentate ligand. The spatial orientation of the four amine groups allows for tetrahedral coordination around metal centers, making it suitable for forming stable complexes with transition metals and lanthanides. This property has led to its evaluation in catalysis and materials synthesis, where metal-organic frameworks or coordination polymers benefit from rigid, polyfunctional building blocks.

The tetramine structure also lends itself to use in host–guest chemistry and the construction of molecular cages. Due to the defined geometry of the amine positions, it can serve as a core unit in the design of larger supramolecular assemblies. Such applications are important in the development of molecular recognition systems, selective encapsulation, and transport of small molecules or ions.

In polymer chemistry, derivatives of tricyclo[3.3.1.1^3,7]decane-1,3,5,7-tetramine have been investigated as crosslinking agents. The multiple amine groups are reactive toward a variety of electrophilic species, including epoxides and isocyanates, facilitating the formation of highly crosslinked polymer networks. This property is useful in the development of thermosetting resins and high-performance materials that require dimensional stability and resistance to thermal or chemical degradation.

Another application area involves the potential use of the tetramine in ion exchange and chelation. The presence of multiple amine functionalities allows the compound to act as a chelating agent, especially in aqueous environments, where it can bind to metal cations through its nitrogen atoms. This function is relevant in analytical chemistry and environmental applications where selective binding and removal of metal ions are required.

Due to the presence of four primary amine groups, tricyclo[3.3.1.1^3,7]decane-1,3,5,7-tetramine is strongly basic and hydrophilic. It exhibits good solubility in water and polar organic solvents, depending on the pH and presence of counterions. The compound’s reactivity is governed largely by the amine groups, which are nucleophilic and capable of undergoing a range of substitution, condensation, and redox reactions. This chemical versatility makes it an adaptable building block in both organic and inorganic synthesis.

Safety handling of tricyclo[3.3.1.1^3,7]decane-1,3,5,7-tetramine requires attention due to the reactive nature of primary amines, which can be irritants and may form potentially harmful products upon degradation. Storage conditions must prevent moisture uptake and oxidative degradation. Proper laboratory procedures, including use of gloves and ventilation, are recommended during its handling.

In summary, tricyclo[3.3.1.1^3,7]decane-1,3,5,7-tetramine is a structurally rigid tetraamine compound with a wide range of well-established applications in coordination chemistry, polymer synthesis, supramolecular assembly, and metal ion binding. Its unique polycyclic structure and multidentate functionality make it valuable for scientific and industrial use in contexts that demand chemical stability, spatial control, and multifunctionality.

References

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