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adamantane

Product name adamantane
Synonyms tricyclo[3.3.1.13,7]decane
GOST no data
CAS 281-23-2

Adamantane is a colorless, easily sublimable crystalline compound with a camphor-like odor. It is soluble in organic solvents, but almost insoluble in water. Adamantane is a cycloalkane with three condenced cyclohexane rings in chair conformation. This diamond-like structure is hard but unstrained. That is why adamantane have an extremely high thermal stability (up to 660°C). Adamantanr can be brominated with liquid bromine to form 1-bromoadamantane. This derivative is a raw material for many other adamantane derivatives. Adamantane was first synthesised by V. Prelog in 1941.

Production.

Adamantane is commercially produced by dicyclopentadiene hydrogenation on platinum catalyst followed by isomerization on aluminium chloride AlCl3 or aluminium bromide AlBr3. This method was found by Schleyer in 1957:

adamantane synthesis from dicyclopentadiene


Uses.

Adamantane is used:

  • in some polymers formulations, which is applied in optical glasses and as thickener in lubricating oil (polyadamantylacrilates);
  • in some dry etching masks;
  • as a common standard for chemical shift referencing in solid-state NMR spectroscopy;
  • in dye lasers to extend the life of the gain medium because it cannot be photoionised due to absence of ultraviolet absorption bands;
  • for the synthesis of antiviral drugs as well as neurological drugs such as rimantadine, amantadine, memantine and Parkinson's disease drugs.

  • Manufacturer(s) no data
    Chemical structure of adamantane

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