Adamantane
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| Adamantane | |
|---|---|
| |
| General | |
| Systematic name | Adamantane |
| Other names | Tricyclo[3.3.1.13,7]decane |
| Molecular formula | C10H16 |
| SMILES | C1C2CC3CC1CC(C2)C3 |
| Molar mass | 136.23 g/mol |
| Appearance | white to off-white powder |
| CAS number | [281-23-2] |
| Properties | |
| Density and phase | 1.07 g/cm3 (20 °C), ? |
| Solubility in water | ? g/100 ml (? °C) |
| Melting point | 270 °C (543 K) |
| Boiling point | ? °C (? K) |
| Acidity (pKa) | ? |
| Basicity (pKb) | ? |
| Chiral rotation | ?° |
| Viscosity | ? cP at ? °C |
| Structure | |
| Crystal structure | face-centered cubic |
| Dipole moment | ? D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | |
| NFPA 704 | |
| Flash point | ? °C |
| R/S statement | R: ? S: 24/25/28/37/45 |
| RTECS number | ? |
| Supplementary data page | |
| Structure and properties | n, εr, etc. |
| Thermodynamic data | Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Related compounds: | memantine, rimantadine, amantadine |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) [Chemical infoboxInfobox disclaimer and references] | |
The first synthesis was done by Prelog in 1941. A more convenient method was found by Schleyerin 1957, using rearrangement reactions.
It melts at 270 °C and in atmospheric pressure sublimes before boiling. It is slightly soluble in water, and has a density of 1.07 g/cm³. Adamantane is very stable hence its name derived from adamant. It is used in polymers to give them special properties. It is also used in pharmacy, as eg. its derivates amantadine and rimantadine. It is also used in some dry etching masks.↑
In solid-state NMR spectroscopy, adamantane is a common standard for chemical shift referencing.
In dye lasers, adamantane may be used to stretch the life of the gain medium; it cannot be photoionized because it lacks ultraviolet absorption bands.
Adamantane derivatives
Adamantane derivatives with application in medicine are amantadine, memantine and rimantadine. Condensed adamantanes or diamondoids have been isolated from petroleum fractions, where they occur in small amounts. These species are of interest as molecular approximations of the cubic diamond framework, terminated with C-H bonds. 1,3-dehydroadamantane is a member of the propellane family.References
External links
- For a full list of external links to MSDSs, spectroscopic data, commercial chemicals suppliers etc. for this compound, see [Chemical sources].
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