1-Bromoadamantane
[CAS# 768-90-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Halogenated aliphatic hydrocarbon
• Name: 1-Bromoadamantane
• Synonyms: 1-Bromotricyclo[3.3.1.1(3,7)]decane
• Molecular Formula: C₁₀H₁₅Br
• Molecular Weight: 215.13
• CAS Registry Number: 768-90-1
• EC Number: 212-200-7
• SMILES: C1C2CC3CC1CC(C2)(C3)Br

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Melting point: 117-121 °C (decomp.) (Expl.)
• Index of Refraction: 1.587, Calc.^*
• Boiling Point: 240.5±9.0 °C (760 mmHg), Calc.^*
• Flash Point: 96.4±8.4 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

1-Bromoadamantane is a chemical compound that belongs to the class of adamantane derivatives. It is a halogenated derivative of adamantane, where a bromine atom is substituted at the 1-position of the adamantane structure. The compound has garnered interest in both research and industrial applications due to its unique structural properties and potential chemical reactivity.

The discovery of adamantane derivatives, including 1-bromoadamantane, dates back to the mid-20th century when the compound adamantane itself was first synthesized and studied for its unique cage-like structure. This structure consists of a fused polycyclic arrangement of carbon atoms, resembling a molecular cage. The versatility of the adamantane structure allowed researchers to explore various modifications of the molecule, leading to the creation of numerous derivatives, including halogenated forms like 1-bromoadamantane.

The synthesis of 1-bromoadamantane typically involves the halogenation of adamantane using bromine, often facilitated by the presence of a catalyst or under specific reaction conditions. This substitution at the 1-position results in the formation of 1-bromoadamantane, which can then be further characterized and analyzed for its chemical and physical properties.

In terms of applications, 1-bromoadamantane has been used in organic synthesis as a reagent in various chemical reactions. Its unique structure makes it a valuable building block for the creation of more complex molecules, especially in the development of new materials or compounds with interesting electronic or structural properties. For instance, it has been explored in the synthesis of novel polymers, where the adamantane framework offers rigidity and stability to the polymer backbone.

Moreover, 1-bromoadamantane has been investigated for its potential use in medicinal chemistry. While not as extensively studied as other adamantane derivatives such as amantadine, which is used as an antiviral and antiparkinsonian drug, 1-bromoadamantane and other halogenated adamantanes have been considered for their biological activity. Research has suggested that such compounds may exhibit interesting pharmacological properties, particularly in the realm of drug design, where the unique structure of adamantane derivatives could influence the binding affinity and activity of various receptors or enzymes.

Additionally, 1-bromoadamantane has found applications in materials science. The adamantane core is known for its high thermal stability and rigid structure, which are desirable properties in certain high-performance materials. As a result, derivatives like 1-bromoadamantane are explored for potential use in electronic materials, coatings, and other applications where stability and mechanical properties are crucial.

Overall, 1-bromoadamantane is an important compound in both synthetic chemistry and material science. Its applications, while diverse, are primarily focused on its use as a building block for more complex molecules and materials. Further research may continue to explore its potential in pharmaceutical and industrial applications, leveraging its unique molecular structure for the development of innovative compounds and materials.

References

1973. Bromination of 2-halo- and 2,2-dihaloadamantanes. Bulletin of the Academy of Sciences of the USSR, Division of chemical science, 22(1).
DOI: 10.1007/bf00854111

2020. A Catalyst-Free, Temperature-Driven One-Pot Synthesis of 1-Adamantylhydrazine Hydrochloride. Synthesis, 53(04).
DOI: 10.1055/s-0040-1707353

2024. Efficient one-pot process for synthesis of antiviral drug amantadine hydrochloride. Journal of Chemical Sciences, 136(2).
DOI: 10.1007/s12039-024-02275-5