TCI
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Description
TCI C2140 5-Chloro-2-adamantanone is an adamantane-derived compound carrying a ketone group at the two position and a chlorine atom at the five position of the rigid adamantane framework. As a non-heterocyclic building block, it is used in organic synthesis laboratories to introduce the three-dimensional, cage-shaped adamantyl skeleton into target molecules. The adamantane framework is known for imparting structural rigidity, a distinctive spatial volume, and high lipophilicity, which is why it is widely applied in drug molecule design, functional materials, and model compounds for structural studies.
The property that makes this compound a preferred choice is the presence of two complementary reactive sites. The ketone group can be elaborated further through reduction, reductive amination, Grignard reactions, Wittig olefination, or the formation of oxime and hydrazone derivatives. Meanwhile, the chlorine atom at the bridgehead position provides a substitution pathway for building doubly substituted adamantane derivatives. The combination of the two allows researchers to design multi-step synthetic routes starting from a single starting material. The rigid adamantane structure also tends to give its derivatives good thermal stability.
In Indonesian laboratories, this building block is typically handled in university organic synthesis groups, medicinal chemistry research units, and industrial or institutional research and development laboratories working on functional molecules. It is generally used at bench scale, where small quantities are weighed out for exploratory reactions, route development, and the preparation of intermediates that are then carried forward to further transformation and characterization steps.
Laboratory Applications
- Medicinal chemistry scaffold construction — the cage-shaped adamantyl framework introduces rigidity and lipophilicity into candidate structures, properties frequently sought when designing drug molecules.
- Ketone functionalization studies — the carbonyl at the two position supports reduction, reductive amination, Grignard addition, and Wittig olefination, giving a single substrate access to several product families.
- Oxime and hydrazone derivative preparation — the ketone group readily forms these nitrogen-containing derivatives, which serve as intermediates or as characterization handles in structural work.
- Synthesis of disubstituted adamantanes — the bridgehead chlorine offers a substitution pathway, letting researchers install a second functional group on the same rigid cage framework.
- Model compound preparation for structural studies — the well-defined, conformationally rigid adamantane skeleton makes derivatives useful as reference structures when investigating molecular geometry and structure-property relationships.
Specifications
- Brand: TCI
- CAS Number: 20098-17-3
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Chemical class: adamantane derivative, non-heterocyclic building block
- Pack sizes: available in standard research-scale packaging as supplied by the manufacturer
- Storage: keep in a tightly closed original container, in a cool, dry, well-ventilated place away from light and moisture
Handling and Storage
Store the material in its tightly closed original container in a cool, dry, well-ventilated area, protected from direct sunlight, moisture, and sources of heat or ignition. Amber glass or the manufacturer's supplied container is suitable; keep the closure secure between uses to limit exposure to atmospheric moisture. Handle in a fume hood using standard personal protective equipment, including safety goggles, gloves, and a laboratory coat, and avoid inhalation of dust or contact with skin and eyes. Weigh out only the quantity required, return the container promptly to storage, and keep it separate from strong oxidizing agents and incompatible reagents. Always consult the manufacturer's safety data sheet before use and dispose of residues according to applicable laboratory waste procedures.
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