Adamantane

Adamantane
Names
	Preferred IUPAC name Adamantane
	Systematic IUPAC name Tricyclo[3.3.1.13,7]decane
Identifiers
CAS Number	281-23-2 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	1901173
ChEBI	CHEBI:40519 ;
ChEMBL	ChEMBL1614830 ;
ChemSpider	8883 ;
DrugBank	DB03627;
ECHA InfoCard	100.005.457
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 Key: ORILYTVJVMAKLC-UHFFFAOYSA-N ; 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)
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
	Occupational safety and health (OHS/OSH):
Main hazards	Flammable
	GHS labelling:
Pictograms
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). verify (what is ?) 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.

^ 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)
^ ^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.
^ 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.
^ Alexander Senning. Elsevier's Dictionary of Chemoetymology. Elsevier, 2006, p. 6 ISBN 0-444-52239-5.

[iupac2013-1] 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)

[r1-2] Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.524. ISBN 978-1-4987-5429-3.

[bagriy_1-3] 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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