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Adamantane information


Adamantane
Skeletal formula of adamantane
Ball-and-stick model of the adamantane molecule
Space-filling model of the adamantane molecule
Sample of adamantane
Names
Preferred IUPAC name
Adamantane[1]
Systematic IUPAC name
Tricyclo[3.3.1.13,7]decane[2]
Identifiers
CAS Number
  • 281-23-2 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
Beilstein Reference
1901173
ChEBI
  • CHEBI:40519 checkY
ChEMBL
  • ChEMBL1614830 ☒N
ChemSpider
  • 8883 checkY
DrugBank
  • DB03627
ECHA InfoCard 100.005.457 Edit this at Wikidata
EC Number
  • 206-001-4
Gmelin Reference
26963
PubChem CID
  • 9238
UNII
  • PJY633525U
CompTox Dashboard (EPA)
  • DTXSID5022017
InChI
  • InChI=1S/C10H16/c1-7-2-9-4-8(1)5-10(3-7)6-9/h7-10H,1-6H2 checkY
    Key: ORILYTVJVMAKLC-UHFFFAOYSA-N checkY
  • InChI=1/C10H16/c1-7-2-9-4-8(1)5-10(3-7)6-9/h7-10H,1-6H2
    Key: ORILYTVJVMAKLC-UHFFFAOYAG
SMILES
  • C1C3CC2CC(CC1C2)C3
  • C1C2CC3CC1CC(C2)C3
Properties
Chemical formula
C10H16
Molar mass 136.238 g·mol−1
Appearance White to off-white powder
Density 1.07 g/cm3 (25 °C)[2]
Melting point 270 °C (518 °F; 543 K)[2]
Boiling point Sublimes[2]
Solubility in water
Poorly soluble
Solubility in other solvents Soluble in hydrocarbons
Refractive index (nD)
1.568[2][3]
Structure
Crystal structure
cubic, space group Fm3m
Coordination geometry
4
Dipole moment
0 D
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Flammable
GHS labelling:
Pictograms
GHS07: Exclamation markGHS09: Environmental hazard
Signal word
Warning
Hazard statements
H319, H400
Precautionary statements
P264, P273, P280, P305+P351+P338, P337+P313, P391, P501
Related compounds
Related compounds:
Memantine
Rimantadine
Amantadine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Adamantane is an organic compound with formula C10H16 or, more descriptively, (CH)4(CH2)6. Adamantane molecules can be described as the fusion of three cyclohexane rings. The molecule is both rigid and virtually stress-free. Adamantane is the most stable isomer of C10H16. The spatial arrangement of carbon atoms in the adamantane molecule is the same as in the diamond crystal. This similarity led to the name adamantane, which is derived from the Greek adamantinos (relating to steel or diamond).[4] It is a white solid with a camphor-like odor. It is the simplest diamondoid.

The discovery of adamantane in petroleum in 1933 launched a new field of chemistry dedicated to the synthesis and properties of polyhedral organic compounds. Adamantane derivatives have found practical application as drugs, polymeric materials, and thermally stable lubricants.

  1. ^ Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 169. doi:10.1039/9781849733069-FP001 (inactive 2024-04-25). ISBN 978-0-85404-182-4. The retained names adamantane and cubane are used in general nomenclature and as preferred IUPAC names.{{cite book}}: CS1 maint: DOI inactive as of April 2024 (link)
  2. ^ a b c d e Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.524. ISBN 978-1-4987-5429-3.
  3. ^ Bagrii, E.I. (1989). Adamantanes: synthesis, properties, applications (in Russian). Nauka. pp. 5–57. ISBN 5-02-001382-X. Archived from the original on 2024-03-08. Retrieved 2016-09-23.
  4. ^ Alexander Senning. Elsevier's Dictionary of Chemoetymology. Elsevier, 2006, p. 6 ISBN 0-444-52239-5.

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