Adamantane

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). It is a white solid with a camphor-like odor. It is the simplest diamondoid.

Not to be confused with Adamantine or Amantadine.
Adamantane
Names
Preferred IUPAC name
Adamantane
Systematic IUPAC name
Tricyclo[3.3.1.13,7]decane
Identifiers
3D model (JSmol)
1901173
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.005.457
EC Number
  • 206-001-4
26963
PubChem CID
UNII
  • InChI=1S/C10H16/c1-7-2-9-4-8(1)5-10(3-7)6-9/h7-10H,1-6H2 Y
    Key: ORILYTVJVMAKLC-UHFFFAOYSA-N Y
  • 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
C10H16
Molar mass 136.238 g·mol−1
Appearance White to off-white powder
Density 1.07 g/cm3 (25 °C)
Melting point 270 °C (518 °F; 543 K)
Boiling point Sublimes
Poorly soluble
Solubility in other solvents Soluble in hydrocarbons
Refractive index (nD)
 1.568
Structure
cubic, space group Fm3m
4
0 D
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Flammable
GHS labelling:
Warning
H319, H400
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).
N verify (what is YN ?)
Infobox references

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.

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