Dihydrolevoglucosenone information

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	14.4 Pa (25 °C) 12.98 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.^[4]^[5]^[6] It is an environmentally friendly alternative to dimethylformamide (DMF) and N-methyl-2-pyrrolidone (NMP).^[7]

^ ^a ^b Jeřábek, Vojtěch; Štejfa, Vojtěch; Klajmon, Martin; Řehák, Karel (15 Nov 2023). "Thermodynamic Properties and Phase Equilibria of Dihydrolevoglucosenone and Its Mixtures with Hydrocarbons". Journal of Chemical & Engineering Data. doi:10.1021/acs.jced.3c00461.
^ ^a ^b ^c Baird, Zachariah Steven; Uusi-Kyyny, Petri; Pokki, Juha-Pekka; Pedegert, Emilie; Alopaeus, Ville (6 Nov 2019). "Vapor Pressures, Densities, and PC-SAFT Parameters for 11 Bio-compounds". International Journal of Thermophysics. 40 (11): 102. Bibcode:2019IJT....40..102B. doi:10.1007/s10765-019-2570-9.
^ Circa Group (23 January 2017). "Safety Data Sheet" (PDF). Archived from the original (PDF) on 19 January 2022. Retrieved 3 February 2019.
^ "Concise and Efficient Synthesis of E-stereoisomers of exo-cyclic Carbohydrate Enones. Aldol Condensation of Dihydrolevoglucosenone with Five-membered Aromatic Aldehydes1 Part 1. - PubAg". pubag.nal.usda.gov. US: United States National Agricultural Library, USA.gov. Retrieved 2019-01-31.
^ Sherwood, James; De bruyn, Mario; Constantinou, Andri; Moity, Laurianne; McElroy, C. Rob; Farmer, Thomas J.; Duncan, Tony; Raverty, Warwick; Hunt, Andrew J. (2014-09-04). "Dihydrolevoglucosenone (Cyrene) as a bio-based alternative for dipolar aprotic solvents". Chem. Commun. 50 (68): 9650–9652. doi:10.1039/c4cc04133j. PMID 25007289.
^ "(1S,5R)-6,8-dioxabicyclo[3.2.1]octan-4-one - Registration Dossier - ECHA". echa.europa.eu. European Chemicals Agency, Europa (web portal). Retrieved 2019-01-31.
^ Clark, James H.; Hunt, Andrew J.; Raverty, Warwick; Duncan, Tony; Farmer, Thomas J.; McElroy, C. Rob; Moity, Laurianne; Constantinou, Andri; Bruyn, Mario De (2014-07-29). "Dihydrolevoglucosenone (Cyrene) as a bio-based alternative for dipolar aprotic solvents". Chemical Communications. 50 (68): 9650–9652. doi:10.1039/C4CC04133J. ISSN 1364-548X. PMID 25007289.

[Jeřábek2023-1] Jeřábek, Vojtěch; Štejfa, Vojtěch; Klajmon, Martin; Řehák, Karel (15 Nov 2023). "Thermodynamic Properties and Phase Equilibria of Dihydrolevoglucosenone and Its Mixtures with Hydrocarbons". Journal of Chemical & Engineering Data. doi:10.1021/acs.jced.3c00461.

[Baird2019-2] Baird, Zachariah Steven; Uusi-Kyyny, Petri; Pokki, Juha-Pekka; Pedegert, Emilie; Alopaeus, Ville (6 Nov 2019). "Vapor Pressures, Densities, and PC-SAFT Parameters for 11 Bio-compounds". International Journal of Thermophysics. 40 (11): 102. Bibcode:2019IJT....40..102B. doi:10.1007/s10765-019-2570-9.

[3] Circa Group (23 January 2017). "Safety Data Sheet" (PDF). Archived from the original (PDF) on 19 January 2022. Retrieved 3 February 2019.

[4] "Concise and Efficient Synthesis of E-stereoisomers of exo-cyclic Carbohydrate Enones. Aldol Condensation of Dihydrolevoglucosenone with Five-membered Aromatic Aldehydes1 Part 1. - PubAg". pubag.nal.usda.gov. US: United States National Agricultural Library, USA.gov. Retrieved 2019-01-31.

[:2-5] Sherwood, James; De bruyn, Mario; Constantinou, Andri; Moity, Laurianne; McElroy, C. Rob; Farmer, Thomas J.; Duncan, Tony; Raverty, Warwick; Hunt, Andrew J. (2014-09-04). "Dihydrolevoglucosenone (Cyrene) as a bio-based alternative for dipolar aprotic solvents". Chem. Commun. 50 (68): 9650–9652. doi:10.1039/c4cc04133j. PMID 25007289.

[6] "(1S,5R)-6,8-dioxabicyclo[3.2.1]octan-4-one - Registration Dossier - ECHA". echa.europa.eu. European Chemicals Agency, Europa (web portal). Retrieved 2019-01-31.

[:1-7] Clark, James H.; Hunt, Andrew J.; Raverty, Warwick; Duncan, Tony; Farmer, Thomas J.; McElroy, C. Rob; Moity, Laurianne; Constantinou, Andri; Bruyn, Mario De (2014-07-29). "Dihydrolevoglucosenone (Cyrene) as a bio-based alternative for dipolar aprotic solvents". Chemical Communications. 50 (68): 9650–9652. doi:10.1039/C4CC04133J. ISSN 1364-548X. PMID 25007289.

Dihydrolevoglucosenone information

and 4 Related for: Dihydrolevoglucosenone information

Dihydrolevoglucosenone

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C6H8O3

Levoglucosenone