2-Methyltetrahydrofuran

2-Methyltetrahydrofuran
Names
	Preferred IUPAC name 2-Methyloxolane
	Other names 2-Methyltetrahydrofuran, 2-Methyl-THF
Identifiers
CAS Number	(Racemic): 96-47-9 ; (R): 63798-13-0; (S): 63798-12-9;
3D model (JSmol)	(Racemic): Interactive image;
ChEMBL	(Racemic): ChEMBL1580503;
ChemSpider	(Racemic): 7028 ;
ECHA InfoCard	100.002.281
EC Number	(Racemic): 202-507-4;
PubChem CID	(Racemic): 7301;
UNII	(Racemic): FCD0VD8ALF ;
UN number	2536
CompTox Dashboard (EPA)	(Racemic): DTXSID9030258;
	InChI InChI=1S/C5H10O/c1-5-3-2-4-6-5/h5H,2-4H2,1H3 Key: JWUJQDFVADABEY-UHFFFAOYSA-N ; (Racemic): InChI=1/C5H10O/c1-5-3-2-4-6-5/h5H,2-4H2,1H3 Key: JWUJQDFVADABEY-UHFFFAOYAM;
	SMILES (Racemic): O1C(C)CCC1;
Properties
Chemical formula	C5H10O
Molar mass	86.134 g·mol−1
Density	0.854 g/mL
Melting point	−136 °C (−213 °F; 137 K)
Boiling point	80.2 °C (176.4 °F; 353.3 K)
Solubility in water	21.0 wt% (0.0 °C); 17.8 wt% (9.5 °C); 14.4 wt% (19.3 °C); 11.4 wt% (29.5 °C); 9.2 wt% (39.6 °C); 7.8 wt% (50.1 °C); 6.6 wt%(60.7 °C); 6.0 wt% (70.6 °C)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H225, H302, H315, H318, H319, H335, H336
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
Safety data sheet (SDS)	External MSDS
	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

2-Methyltetrahydrofuran (2-MeTHF) is an organic compound with the molecular formula C₅H₁₀O. It is a highly flammable, mobile liquid. It is mainly used as a replacement for Tetrahydrofuran (THF) in specialized applications for its better performance, such as to obtain higher reaction temperatures, or easier separations (as, unlike THF, it is not miscible with water). It is derived from sugars via furfural and is occasionally touted as a biofuel.^[3]

^ Sicaire, Anne-Gaëlle; Vian, Maryline Abert; Filly, Aurore; Li, Ying; Bily, Antoine; Chemat, Farid (2014), Chemat, Farid; Vian, Maryline Abert (eds.), "2-Methyltetrahydrofuran: Main Properties, Production Processes, and Application in Extraction of Natural Products", Alternative Solvents for Natural Products Extraction, Berlin, Heidelberg: Springer Berlin Heidelberg, pp. 253–268, doi:10.1007/978-3-662-43628-8_12, ISBN 978-3-662-43627-1
^ ^a ^b Cite error: The named reference aycock was invoked but never defined (see the help page).
^ Leal Silva, Jean Felipe; Mariano, Adriano Pinto; Maciel Filho, Rubens (2018). "Economic potential of 2-methyltetrahydrofuran (MTHF) and ethyl levulinate (EL) produced from hemicelluloses-derived furfural". Biomass and Bioenergy. 119 (December 2018): 492–502. doi:10.1016/j.biombioe.2018.10.008. S2CID 104836889.

[1] Sicaire, Anne-Gaëlle; Vian, Maryline Abert; Filly, Aurore; Li, Ying; Bily, Antoine; Chemat, Farid (2014), Chemat, Farid; Vian, Maryline Abert (eds.), "2-Methyltetrahydrofuran: Main Properties, Production Processes, and Application in Extraction of Natural Products", Alternative Solvents for Natural Products Extraction, Berlin, Heidelberg: Springer Berlin Heidelberg, pp. 253–268, doi:10.1007/978-3-662-43628-8_12, ISBN 978-3-662-43627-1

[aycock-2] Cite error: The named reference aycock was invoked but never defined (see the help page).

[3] Leal Silva, Jean Felipe; Mariano, Adriano Pinto; Maciel Filho, Rubens (2018). "Economic potential of 2-methyltetrahydrofuran (MTHF) and ethyl levulinate (EL) produced from hemicelluloses-derived furfural". Biomass and Bioenergy. 119 (December 2018): 492–502. doi:10.1016/j.biombioe.2018.10.008. S2CID 104836889.

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