Adamantane

Title: Adamantane
CAS Registry Number: 281-23-2
CAS Name: Tricyclo[3.3.1.13,7]decane
Additional Names: diamantane (obsolete)
Molecular Formula: C10H16
Molecular Weight: 136.23
Percent Composition: C 88.16%, H 11.84%
Literature References: Isoln from petroleum from Moravia province in Czechoslovakia: Landa, Machacek, Collect. Czech. Chem. Commun. 3, 1 (1933); from American petroleum: Mair et al., Anal. Chem. 31, 2082 (1959). Synthesis: Prelog, Seiwerth, Ber. 74, 1769 (1941); Stetter et al., Ber. 89, 1922 (1956); by aluminum chloride-catalyzed isomerization of tetrahydrodicyclopentadiene: Yan, Shreh, Bull. Inst. Chem. Acad. Sinica Dec. 1965, no. 11, pp 79-81. Two step synthesis starting with dicyclopentadiene: Schleyer, J. Am. Chem. Soc. 79, 3292 (1957); Schleyer, Donaldson, ibid. 82, 4645 (1960); Ludwig US 2937211 (1960 to du Pont). Reviews: Stetter, Angew. Chem. 66, 217 (1954); Fort, Schleyer, Chem. Rev. 64, 277 (1964).
Properties: Crystallizes at -30°; can be purified by recrystallization from acetone or by sublimination. mp 269.6-270.8°.
Melting point: mp 269.6-270.8°
NOTE: The name diamantane has been abandoned as a synonym for adamantane and proposed as the name for the second member of the adamantane series, congressane: Vogl, Anderson, Tetrahedron Lett. 1966, 415.
Use: The diamine as curing agent for epoxy resins [US 3053907 (1962 to du Pont)].
Adapalene Adefovir A-Denopterin Adenosine Adenosine Diphosphate

Adamantane
Skeletal formula with numbering convention Ball-and-stick model
Adamantane crystals
Identifiers
CAS number 281-23-2 YesY
PubChem 9238
ChemSpider 8883 YesY
ChEBI CHEBI:40519 YesY
ChEMBL CHEMBL1614830 N
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C10H16
Molar mass 136.23 g mol−1
Appearance White to off-white powder
Density 1.08 g/cm3 (20 °C),[2] solid
Melting point 270 °C; 518 °F; 543 K
Boiling point Sublimes
Solubility in water Poorly soluble
Solubility in other solvents Soluble in hydrocarbons
Refractive index (nD) 1.568[3]
Structure
Crystal structure cubic, space group Fm3m
Coordination
geometry
4
Dipole moment 0 D
Hazards
S-phrases 24/25/28/37/45
Main hazards Flammable
Related compounds
Related compounds: Memantine
Rimantadine
Amantadine
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Adamantane is a colorless, crystalline chemical compound with a camphor-like odor. With a formula C10H16, it is a cycloalkane and also the simplest diamondoid. Adamantane molecules consist of four connected cyclohexane rings arranged in the "armchair" configuration. It is unique in that it is both rigid and virtually stress-free. A boat shaped configuration can also exist. Adamantane is the most stable among all the isomers with formula C10H16, which include the somewhat similar twistane. The spatial arrangement of carbon atoms is the same in adamantane molecule and in the diamond crystal. This motivates the name adamantane, which is derived from the Greek adamantinos (relating to steel or diamond).[4]

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