Dihydrolevoglucosenone

Dihydrolevoglucosenone
Names
	IUPAC name (1R,5S)-7,8-Dioxabicyclo[3.2.1]octan-2-one
	Other names Cyrene
Identifiers
CAS Number	53716-82-8;
3D model (JSmol)	Interactive image;
ChemSpider	9150700;
ECHA InfoCard	100.234.612
EC Number	807-130-4;
PubChem CID	16762483;
CompTox Dashboard (EPA)	DTXSID30450332 ;
	InChI InChI=1S/C6H8O3/c7-5-2-1-4-3-8-6(5)9-4/h4,6H,1-3H2/t4-,6+/m0/s1 Key: WHIRALQRTSITMI-UJURSFKZSA-N;
	SMILES [C@H]12CCC([C@H](OC1)O2)=O;
Properties
Chemical formula	C6H8O3
Molar mass	128.127 g·mol−1
Appearance	clear to yellowish liquid
Density	1.2473 g/cm3 (25 °C)
Boiling point	226 °C (439 °F; 499 K)
Solubility in water	miscible
Vapor pressure	12.98 Pa (25 °C) 14.4 Pa (25 °C)
Refractive index (nD)	1.4732 (20 °C)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H319
Precautionary statements	P305+P351+P338, P313
Flash point	108 °C (226 °F; 381 K)
Autoignition; temperature	296 °C (565 °F; 569 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Dihydrolevoglucosenone (Cyrene) is a bicyclic, chiral, seven-membered heterocyclic cycloalkanone which is a waste derived and fully biodegradable aprotic dipolar solvent. It is an environmentally friendly alternative to dimethylformamide (DMF) and N-methyl-2-pyrrolidone (NMP).