Adamantanone

Adamantanone is the ketone of adamantane. A white solid, it is prepared by oxidation of adamantane.^[1] It is a precursor to several adamantane derivatives.^[2]

Quick facts Names, Identifiers ...

Adamantanone

Names
Preferred IUPAC name Adamantan-2-one
Other names Tricyclo[3.3.1.13,7]decanone 2-Adamantanone
Identifiers
CAS Number	700-58-3
3D model (JSmol)	Interactive image
ChEBI	CHEBI:40611
ChEMBL	ChEMBL2041316
ChemSpider	57725
DrugBank	DB02125
ECHA InfoCard	100.010.772
EC Number	211-847-2
Gmelin Reference	122962
PubChem CID	64151
UNII	UI7W503L08
CompTox Dashboard (EPA)	DTXSID9022108
InChI InChI=1S/C10H14O/c11-10-8-2-6-1-7(4-8)5-9(10)3-6/h6-9H,1-5H2 Key: IYKFYARMMIESOX-UHFFFAOYSA-N
SMILES C1C2CC3CC1CC(C2)C3=O
Properties
Chemical formula	C10H14O
Molar mass	150.221 g·mol−1
Appearance	white solid
Melting point	270 °C (518 °F; 543 K)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H315, H318, H410
Precautionary statements	P264, P270, P273, P280, P301+P310, P302+P352, P305+P351+P338, P310, P321, P330, P332+P313, P362, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Close

Adamantanone and some related polycyclic ketones, are reluctant to form enolates. This barrier arises because the resulting carbanion cannot exist in conjugation with the carbonyl pi-bond.^[3][4][5]