2-Cumaranone

2-Cumaranone
Names
	IUPAC name 3H-1-benzofuran-2-one
Identifiers
CAS Number	553-86-6 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL284584;
ChemSpider	61668;
ECHA InfoCard	100.008.230
EC Number	209-052-0;
PubChem CID	68382;
UNII	4K47Z4Q1E7;
CompTox Dashboard (EPA)	DTXSID70203829 ;
	InChI InChI=1S/C8H6O2/c9-8-5-6-3-1-2-4-7(6)10-8/h1-4H,5H2 Key: ACZGCWSMSTYWDQ-UHFFFAOYSA-N;
	SMILES C1C2=CC=CC=C2OC1=O;
Properties
Chemical formula	C8H6O2
Melting point	49–51 °C
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H317, H319
Precautionary statements	P261, P264, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P332+P317, P333+P317, P337+P317, P362+P364, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2-Cumaranone is a bicyclic heteroaromatic compound in which a six-membered benzene ring is annulated with a five-membered γ-butyrolactone ring. The 2(3H)-benzofuranone can also be considered as a lactone of (2-hydroxyphenyl)acetic acid. The benzofuranone basic structure is the basis of some natural products – such as rosmadial,^[3] which is isolatable from rosemary oil, and some substances with high pharmacological activity, such as griseofulvin and rifampicin. Furthermore, 2-cumaranone is utilized as a starting material for the preparation of chemiluminescent and fluorescent dyes, for synthetic pharmaceutical agents, like the antiarrhythmic drug dronedarone, and especially for the fungicide azoxystrobin.

^ Sigma-Aldrich Co., product no. {{{id}}}.
^ "2-Coumaranone". pubchem.ncbi.nlm.nih.gov.
^ N. Nakatani; R. Inatani (1983), "A New Diterpene Lactone, Rosmadial, from Rosemary (Rosmarinus officinalis L.)", Biosci. Biotechnol. Biochem., vol. 47, no. 2, pp. 353–358, doi:10.1080/00021369.1983.10865620