Adamantane

Adamantane

Names
Preferred IUPAC name Adamantane
Systematic IUPAC name Tricyclo[3.3.1.13,7]decane
Identifiers
CAS Number	281-23-2 Y
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:40519 Y
ChEMBL	ChEMBL1614830 N
ChemSpider	8883 Y
ECHA InfoCard	100.005.457
PubChem	9238
InChI 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
Chemical formula	C10H16
Molar mass	136.24 g·mol−1
Appearance	White to off-white powder
Density	1.08 g/cm3 (20 °C), 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
Structure
Crystal structure	cubic, space group Fm3m
Coordination geometry	4
Dipole moment	0 D
Hazards
Main hazards	Flammable
S-phrases	24/25/28/37/45
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  (what is YN ?)
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 in adamantane molecule is the same as in the diamond crystal. This motivates the name adamantane, which is derived from the Greek adamantinos (relating to steel or diamond).

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

The possibility of the existence of a hydrocarbon with the C₁₀H₁₆ formula and diamond-like structure of the molecule was suggested by H. Decker at a conference in 1924. Decker called this molecule decaterpene and was surprised that it had not been synthesized yet.

The first attempt of laboratory synthesis was made by German chemist Hans Meerwein in 1924 using reaction of formaldehyde with diethyl malonate in the presence of piperidine. Instead of adamantane, Meerwein obtained 1,3,5,7-tetracarbomethoxybicyclo[3.3.1]nonane-2,6-dione. This compound was later named Meerwein's ester and used in the syntheses of adamantane and its derivatives. Later, another German chemist D. Bottger tried to obtain adamantane using Meerwein's ester as precursor. However, the product, tricyclo-[3.3.1.1^3,7] decane ring system, was again an adamantane derivative.