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			{{short description|Cyclic chemical compound, (CH₂)₄O}}
	{{redirect|THF}}		{{redirect|THF}}
	{{chembox		{{chembox
			| Verifiedfields = changed
	| verifiedrevid = 398940365
			| Watchedfields = changed
			| verifiedrevid = 418146341
	| Name = Tetrahydrofuran		| Name = Tetrahydrofuran
			| ImageFileL1_Ref = {{chemboximage|correct|??}}
	| ImageFileL1 = Tetrahydrofuran-2D-skeletal-A.png
			| ImageFileL1 = Structural formula of tetrahydrofuran.svg
	| ImageSize = 100px
			| ImageSizeL1 = 90px
	| ImageName = Skeletal formula of tetrahydrofuran
			| ImageNameL1 = Skeletal formula of tetrahydrofuran
	| ImageFileR1 = Tetrahydrofuran-3D-balls.png		| ImageFileR1 = Tetrahydrofuran-3D-balls.png
	| ImageSizeR1 = 120px		| ImageSizeR1 = 120px
	| ImageNameR1 = Space-filling model of the THF molecule		| ImageNameR1 = Ball-and-stick model of the tetrahydrofuran molecule
			| ImageFile2 = Tetrahydrofuran sample.jpg
	| IUPACName = Oxolane
			| ImageName2 = Photograph of a glass bottle of tetrahydrofuran
	| OtherNames = THF, tetrahydrofuran, 1,4-epoxybutane, butylene oxide, cyclotetramethylene oxide, oxacyclopentane, diethylene oxide, furanidine, hydrofuran, tetra-methylene oxide
			| ImageSize2 = 175px
	| Section1 = {{Chembox Identifiers
			| PIN = Oxolane<ref>{{cite web|url=http://bulletin.acscinf.org/PDFs/247nm44.pdf|title=New IUPAC Organic Nomenclature - Chemical Information BULLETIN}}</ref><!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) -->
			| SystematicName = 1,4-Epoxybutane<br />1-Oxacyclopentane
			| OtherNames = Tetrahydrofuran<br />THF<br />1,4-Butylene oxide<br />Cyclotetramethylene oxide fraction<br />Furanidin<br />Tetra-methylene oxide, Oxolane
			|Section1={{Chembox Identifiers
			| ChEBI_Ref = {{ebicite|changed|EBI}}
			| ChEBI = 26911
	| SMILES = C1CCOC1		| SMILES = C1CCOC1
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
Line 18:		Line 28:
	| InChI = 1/C4H8O/c1-2-4-5-3-1/h1-4H2		| InChI = 1/C4H8O/c1-2-4-5-3-1/h1-4H2
	| InChIKey = WYURNTSHIVDZCO-UHFFFAOYAI		| InChIKey = WYURNTSHIVDZCO-UHFFFAOYAI
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 276521		| ChEMBL = 276521
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
Line 23:		Line 34:
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = WYURNTSHIVDZCO-UHFFFAOYSA-N		| StdInChIKey = WYURNTSHIVDZCO-UHFFFAOYSA-N
			| Abbreviations = THF
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 109-99-9		| CASNo = 109-99-9
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 3N8FZZ6PY4
	| RTECS = LU5950000		| RTECS = LU5950000
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
			| C=4 | H=8 | O=1
	| Formula = C<sub>4</sub>H<sub>8</sub>O
			| Appearance = Colorless liquid
	| MolarMass = 72.11 g/mol
			| Odor = Ether-like<ref name=PGCH/>
	| Appearance = colorless liquid
			| Density = 0.8876{{nbsp}}g/cm<sup>3</sup> at 20{{nbsp}}°C, liquid <ref name="Baird2019">{{cite journal |last1=Baird |first1=Zachariah Steven |last2=Uusi-Kyyny |first2=Petri |last3=Pokki |first3=Juha-Pekka |last4=Pedegert |first4=Emilie |last5=Alopaeus |first5=Ville |title=Vapor Pressures, Densities, and PC-SAFT Parameters for 11 Bio-compounds |journal=International Journal of Thermophysics |date=6 Nov 2019 |volume=40 |issue=11 |page=102 |doi=10.1007/s10765-019-2570-9|bibcode=2019IJT....40..102B |doi-access=free }}</ref>
	| Density = 0.8892 g/cm<sup>3</sup> (g/mL) @ 20 °C, liquid
	| Solubility = Miscible		| Solubility = ]
	| MeltingPt = −108.4 °C (164.75 K)		| MeltingPtC = −108.4
	| BoilingPt = 66 °C (339.15 K)		| BoilingPtC = 66
			| BoilingPt_ref = <ref>NIST Chemistry WebBook. http://webbook.nist.gov</ref><ref name="Baird2019" />
	| Viscosity = 0.48 cP at 25 °C
			| Viscosity = 0.48{{nbsp}}cP at 25{{nbsp}}°C
			| VaporPressure = 132{{nbsp}}mmHg at 20{{nbsp}}°C<ref name=PGCH/>
			| RefractIndex = 1.4073 at 20{{nbsp}}°C<ref name="Baird2019" />
	}}		}}
	| Section3 = {{Chembox Structure		|Section3={{Chembox Structure
	| MolShape = envelope		| MolShape = ]
	| Dipole = 1.63 ] (gas)		| Dipole = 1.63{{nbsp}}] (gas)
	}}		}}
	| Section7 = {{Chembox Hazards		|Section7={{Chembox Hazards
	| EUClass = Flammable ('''F''')<br />Irritant ('''Xi''')
	| NFPA-H = 2		| NFPA-H = 2
	| NFPA-F = 3|Reactivity=1		| NFPA-F = 3
	| NFPA-R =		| NFPA-R = 1
			| NFPA-S =
	| RPhrases = {{R11}}, {{R19}}, {{R36/37}}
			| GHSPictograms = {{GHS02}} {{GHS07}} {{GHS08}}<ref name="GESTIS">{{GESTIS|ZVG=25400 |CAS=109-99-9 |Name=Tetrahydrofuran |Date=2 June 2020 }}</ref>
	| SPhrases = {{S16}}, {{S29}}, {{S33}}
			| GHSSignalWord = '''Danger'''
	| FlashPt = −14 °C
			| HPhrases = {{H-phrases|225|302|319|335|351}}<ref name=GESTIS/>
			| PPhrases = {{P-phrases|210|280|301+312+330|305+351+338|370+378|403+235}}<ref name=GESTIS/>
			| FlashPtC = −14
			| PEL = TWA 200{{nbsp}}ppm (590{{nbsp}}mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0602}}</ref>
			| ExploLimits = 2–11.8%<ref name = PGCH/>
			| IDLH = 2000{{nbsp}}ppm<ref name=PGCH/>
			| REL = TWA 200{{nbsp}}ppm (590{{nbsp}}mg/m<sup>3</sup>) ST 250{{nbsp}}ppm (735{{nbsp}}mg/m<sup>3</sup>)<ref name=PGCH/>
			| LC50 = 21000{{nbsp}}ppm (rat, 3{{nbsp}}h)<ref name=IDLH>{{IDLH|109999|Tetrahydrofuran}}</ref>
			| LD50 = {{ubl
			| 1650{{nbsp}}mg/kg (rat, oral)
			| 2300{{nbsp}}mg/kg (mouse, oral)
			| 2300{{nbsp}}mg/kg (guinea pig, oral)<ref name=IDLH/>
	}}		}}
			}}<ref>{{cite web|url=http://www.newenv.com/resources/nfpa_chemicals/#S |title=New Environment Inc. - NFPA Chemicals |website=Newenv.com |access-date=2016-07-16}}</ref>
	| Section8 = {{Chembox Related
			|Section8={{Chembox Related
	| Function = ]s
			| OtherFunction_label = ]s
	| OtherFunctn = ]<br />]<br />]
			| OtherFunction = ]<br />]<br />]
	| OtherCpds = ]
			| OtherCompounds = ]
	}}		}}
	}}		}}
	'''Tetrahydrofuran''' ('''THF''') is a colorless, water-] organic liquid with low ] at ]. This ] compound has the chemical formula (CH<sub>2</sub>)<sub>4</sub>O. As one of the most ] ]s with a wide liquid range, it is a useful solvent. Its main use, however, is as a precursor to polymers. THF has an odor similar to its chemical cousin, ], but is a much less potent ] than diethyl ether.		'''Tetrahydrofuran''' ('''THF'''), or '''oxolane''', is an ] with the formula (CH<sub>2</sub>)<sub>4</sub>O. The compound is classified as ], specifically a cyclic ]. It is a colorless, water-] organic liquid with low ]. It is mainly used as a ] to polymers.<ref name=Ullmann/> Being ] and having a wide liquid range, THF is a versatile ]. It is an isomer of another solvent, ].
	==Production==		==Production==
	About two hundred thousand tonnes of tetrahydrofuran are produced annually.<ref name="kirk1">{{cite encyclopedia		About 200,000 ]s of tetrahydrofuran are produced annually.<ref name="kirk1">{{cite encyclopedia
	|title =Ethers, by Lawrence Karas and W. J. Piel|encyclopedia =Kirk‑Othmer Encyclopedia of Chemical Technology|volume =|pages =|publisher =John Wiley & Sons, Inc|year =2004}}</ref> The most widely used industrial process involves the acid-catalyzed dehydration of ], akin to the production of ] from ]. The butanediol is derived from ] of ] followed by ]. ] developed a process for producing THF by ] ] to crude ] followed by catalytic hydrogenation.<ref name="merck">''Merck Index of Chemicals and Drugs'', 9th ed.</ref> A third major industrial route entails ] of ] followed by hydrogenation to the butanediol.		| title =Ethers |first1= Lawrence|last1= Karas|first2= W. J.|last2= Piel|encyclopedia =Kirk‑Othmer Encyclopedia of Chemical Technology|publisher =John Wiley & Sons|year =2004}}</ref> The most widely used industrial process involves the acid-catalyzed dehydration of ]. ] is one of the biggest producers of this chemical route. The method is similar to the production of ] from ]. The butanediol is derived from ] of ] with ] followed by ].<ref name=Ullmann/> ] developed a process for producing THF by ] ] to crude ], followed by catalytic hydrogenation.<ref name="merck">{{Merck13th}}</ref> A third major industrial route entails ] of ] followed by hydrogenation to ].
			===Other methods===
	THF can also be synthesized by catalytic hydrogenation of ].<ref name="m_and_b">Morrison, Robert Thornton; Boyd, Robert Neilson: ''Organic Chemistry'', 2nd ed., Allyn and Bacon 1972, p. 569</ref><ref>{{OrgSynth | title = Tetrahydrofuran | author = Donald Starr and R. M. Hixon | prep = cv2p0566 | collvol = 2 | collvolpages = 566 | year = 1943}}</ref> Where furan is derived from ], this method can involve renewable resources. Nevertheless, this route is not widely practiced.
			THF can also be synthesized by catalytic hydrogenation of ].<ref name="m_and_b">{{cite book|last1=Morrison|first1=Robert Thornton|last2=Boyd|first2=Robert Neilson|title=Organic Chemistry|edition=2nd|publisher=Allyn and Bacon|date=1972|page=569}}</ref><ref>{{OrgSynth | title = Tetrahydrofuran | first1 = Donald | last1 = Starr | first2 = R. M. | last2 = Hixon | prep = cv2p0566 | collvol = 2 | collvolpages = 566 | year = 1943}}</ref> This allows ] to be converted to THF via acid-catalyzed digestion to ] and ] to furan,<ref>{{Citation|last1=Hoydonckx|first1=H. E.|title=Furfural and Derivatives|date=2007|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|publisher=American Cancer Society|language=en|doi=10.1002/14356007.a12_119.pub2|isbn=978-3-527-30673-2|last2=Rhijn|first2=W. M. Van|last3=Rhijn|first3=W. Van|last4=Vos|first4=D. E. De|last5=Jacobs|first5=P. A.}}</ref> although this method is not widely practiced. THF is thus derivable from renewable resources.
	==Applications==		==Applications==
			===Polymerization===
	THF can be ] by strong acids to give a linear polymer called ] (PTMEG), ] , also known as PTMO, polytetramethylene oxide. The primary use of this polymer is to make ] ] fibers like ].<ref name="kirk">{{cite encyclopedia |year=1996 |title =Polyethers, Tetrahydrofuran and Oxetane Polymers by Gerfried Pruckmayr, P. Dreyfuss, M. P. Dreyfuss |encyclopedia=Kirk‑Othmer Encyclopedia of Chemical Technology |publisher=John Wiley & Sons, Inc |location= |id= }}</ref>
			In the presence of ]s, THF converts to a linear polymer called ] (PTMEG), also known as polytetramethylene oxide (PTMO):
			:<math chem>
			n \, \ce{C4H8O} \quad \xrightarrow{} \quad \bigl_n
			</math>
			This polymer is primarily used to make ] ] fibers like ].<ref name="kirk">{{cite encyclopedia |year=1996 |title =Polyethers, Tetrahydrofuran and Oxetane Polymers |first1= Gerfried|last1= Pruckmayr|first2= P.|last2= Dreyfuss|first3= M. P.|last3= Dreyfuss |encyclopedia=Kirk‑Othmer Encyclopedia of Chemical Technology |publisher=John Wiley & Sons }}</ref>
	===As a solvent===		===As a solvent===
	The other main application of THF is as an industrial solvent for ] and in ]es.<ref>Herbert Müller, "Tetrahydrofuran" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a26_221}}</ref> It is an ] ] with a ] of 7.6. It is a moderately polar solvent and can dissolve a wide range of nonpolar and polar chemical compounds.<ref>{{cite web|url=http://www.cem.msu.edu/~reusch/VirtualText/enrgtop.htm#top4 |title=Chemical Reactivity |publisher=Cem.msu.edu |date= |accessdate=2010-02-15}}</ref> THF is water-miscible, and can form solid ] structures with water at low temperatures.<ref>{{cite web|url=http://gashydrate.fileave.com/NMR-MRI%20study%20of%20clathrate%20hydrate%20mechanisms.pdf |title=FileAve.com |publisher=Gashydrate.fileave.com |date= |accessdate=2010-02-15}}</ref>		The other main application of THF is as an industrial solvent for ] (PVC) and in ]es.<ref name=Ullmann>{{Ullmann|first=Herbert |last=Müller |title=Tetrahydrofuran |doi=10.1002/14356007.a26_221}}</ref> It is an ] ] with a ] of 7.6. It is a moderately polar solvent and can dissolve a wide range of nonpolar and polar chemical compounds.<ref>{{cite web |url=http://www.cem.msu.edu/~reusch/VirtualText/enrgtop.htm#top4 |title=Chemical Reactivity |publisher=Michigan State University |access-date=2010-02-15 |archive-url=https://web.archive.org/web/20100316211430/http://www.cem.msu.edu/~reusch/VirtualText/enrgtop.htm#top4 |archive-date=2010-03-16 }}</ref> THF is water-miscible and can form solid ] structures with water at low temperatures.<ref>{{cite web |url=http://gashydrate.fileave.com/NMR-MRI%20study%20of%20clathrate%20hydrate%20mechanisms.pdf |title=NMR–MRI study of clathrate hydrate mechanisms |website=Fileave.com |access-date=2010-02-15 |archive-url=https://web.archive.org/web/20110711000808/http://gashydrate.fileave.com/NMR-MRI%20study%20of%20clathrate%20hydrate%20mechanisms.pdf |archive-date=2011-07-11 }}</ref>
			THF has been explored as a miscible co-solvent in aqueous solution to aid in the liquefaction and delignification of plant ] for production of renewable platform chemicals and ] as potential precursors to ].<ref name="pubs.rsc.org">{{cite journal|last1=Cai|first1=Charles|last2=Zhang|first2=Taiying|last3=Kumar|first3=Rajeev|last4=Wyman|first4=Charles|title=THF co-solvent enhances hydrocarbon fuel precursor yields from lignocellulosic biomass|journal=Green Chemistry|date=13 August 2013|volume=15|issue=11|pages=3140–3145|doi=10.1039/C3GC41214H}}</ref> Aqueous THF augments the hydrolysis of ] from biomass and dissolves the majority of biomass lignin making it a suitable solvent for biomass pretreatment.
	===Laboratory use===
	Although a minor application, THF is a popular solvent in the laboratory when a moderately higher-boiling ethereal solvent is required and its water miscibility is not an issue. The oxygen center of ethers can coordinate to ]s such as Li<sup>+</sup>, Mg<sup>2+</sup>, and ]s, forming ]s. Hence, like diethyl ether, THF can be used in ] reactions to synthesize ], and as a solvent for ]s such as ] and ]s.<ref>Elschenbroich, C.; Salzer, A. ”Organometallics : A Concise Introduction” (2nd Ed) (1992) Wiley-VCH: Weinheim. ISBN 3-527-28165-7</ref> Although similar to diethyl ether, THF is a stronger base.<ref>E.g., B.L. Lucht, D.B. Collum "Lithium Hexamethyldisilazide: A View of Lithium Ion Solvation through a Glass-Bottom Boat" Accounts of Chemical Research, 1999, volume 32, 1035–1042 {{doi|10.1021/ar960300e}}, and references therein.</ref> Thus, while diethyl ether remains the solvent of choice for some reactions (e.g., Grignard reactions), THF fills that role in many others where strong coordination is desirable, and the precise properties of ethereal solvents such as these (alone and in mixtures and at various temperatures) allows for fine-tuning modern chemical reactions.
	THF is often used in polymer science. For example, it can be used to dissolve ] prior to determining its molecular mass using ]. THF dissolves PVC as well and is the main ingredient in PVC adhesives. It can be used to liquefy old PVC cement, and is often used industrially to ] metal parts.		THF is often used in polymer science. For example, it can be used to dissolve ] prior to determining their molecular mass using ]. THF dissolves PVC as well, and thus it is the main ingredient in PVC adhesives. It can be used to liquefy old PVC cement and is often used industrially to ] metal parts.
			THF is used as a component in mobile phases for ]. It has a greater elution strength than ] or ], but is less commonly used than these solvents.
	====2-MethylTHF====
	] (2MeTHF) is a THF alternative that is being promoted as being more ecologically friendly.<ref>{{cite web|url=http://www.sigmaaldrich.com/etc/medialib/docs/Sigma/Brochure/greener_solvent_alternatives.Par.0001.File.tmp/greener_solvent_alternatives.pdf |title=Greener Solvent Alternatives - Brochure |format=PDF |date= |accessdate=2010-02-15}}</ref> Whereas 2-MeTHF is more expensive, it may provide for greater overall process economy. 2MeTHF has solvating properties that are intermediate between diethyl ether and THF, has limited water-miscibility, and forms an ] with water on distillation. Its lower melting point makes it useful for lower temperature reactions, and its higher boiling point allows procedures under reflux at higher temperatures (relative to THF).
			THF is used as a solvent in 3D printing when printing with ], ] and substantially similar filaments. It can be used to clean clogged 3D printer parts, to remove extruder lines and add a shine to the finished product as well as to ] printed parts.
			====Laboratory use====
			In the laboratory, THF is a popular solvent when its water miscibility is not an issue. It is more ] than diethyl ether<ref>{{cite journal | last1 = Lucht | first1 = B. L. | last2 = Collum | first2 = D. B. | year = 1999 | title = Lithium Hexamethyldisilazide: A View of Lithium Ion Solvation through a Glass-Bottom Boat | journal = Accounts of Chemical Research | volume = 32 | issue = 12| pages = 1035–1042 | doi = 10.1021/ar960300e }}</ref> and forms stronger ] with ], ], and ]s. It is a popular solvent for ] reactions and for ]s such as ] and ]s.<ref>{{cite book|last1=Elschenbroich |first1=C. |last2=Salzer |first2=A. |title=Organometallics: A Concise Introduction |edition=2nd |date=1992 |publisher=Wiley-VCH |location=Weinheim |isbn=3-527-28165-7}}</ref> Thus, while diethyl ether remains the solvent of choice for some reactions (e.g., Grignard reactions), THF fills that role in many others, where strong coordination is desirable and the precise properties of ethereal solvents such as these (alone and in mixtures and at various temperatures) allows fine-tuning modern chemical reactions.
			Commercial THF contains substantial water that must be removed for sensitive operations, e.g. those involving ]s. Although THF is traditionally dried by ] from an aggressive ] such as elemental ], ]s have been shown to be superior water scavengers.<ref>{{cite journal|last1=Williams |first1=D. B. G. |last2=Lawton |first2=M. |title=Drying of Organic Solvents: Quantitative Evaluation of the Efficiency of Several Desiccants |journal=Journal of Organic Chemistry |date=2010 |volume=75 |issue=24 |pages=8351–4 |doi=10.1021/jo101589h |pmid=20945830|s2cid=17801540 }}</ref>
			====Reaction with hydrogen sulfide====
			In the presence of a ], THF reacts with ] to give ].<ref>{{Ullmann|first=Jonathan|last=Swanston|title=Thiophene|doi=10.1002/14356007.a26_793.pub2}}</ref>
			==Lewis basicity==
			]
			THF is a Lewis base that bonds to a variety of ] such as ], ], ] and ]. THF has been classified in the ] and it has been shown that there is no one order of base strengths.<ref>{{cite journal|author1=Vogel G. C. |author2=Drago, R. S. |year=1996|journal=Journal of Chemical Education|volume=73|pages=701–707|title=The ECW Model|issue=8 |bibcode=1996JChEd..73..701V|doi=10.1021/ed073p701}}</ref> Many complexes are of the stoichiometry MCl<sub>3</sub>(THF)<sub>3</sub>.<ref>Manzer, L. E. "Tetrahydrofuran Complexes of Selected Early Transition Metals," ''Inorganic Synthesis''. 21, 135–140, (1982).</ref>
	==Precautions==		==Precautions==
	THF is considered a relatively nontoxic solvent, with the ] (LD<sub>50</sub>) comparable to that for ]. Reflecting its remarkable solvent properties, it penetrates the skin causing rapid dehydration. THF readily dissolves latex and is typically handled with nitrile or neoprene rubber gloves. It is highly flammable.		THF is a relatively acutely nontoxic solvent, with the ] (LD<sub>50</sub>) comparable to that for ]. However, chronic exposure is suspected of causing cancer.<ref name=GESTIS/><ref>{{cite web |url=https://fscimage.fishersci.com/msds/23011.htm |title=Material Safety Data Sheet Tetrahydrofuran, 99.5+%, for spectroscopy. |website=Fisher Scientific |access-date=2022-07-27}}</ref> Reflecting its remarkable solvent properties, it penetrates the skin, causing rapid dehydration. THF readily dissolves latex and thus should be handled with ] gloves. It is highly flammable.
	The greatest danger posed by THF follows from its tendency to form highly-explosive ]s on storage in air. To minimize this problem, commercial samples of THF are often inhibited with ]. THF should not be distilled to dryness, because the explosive peroxides concentrate in the residue.		One danger posed by THF is its tendency to form the explosive compound ] upon reaction with air:
			:]
			To minimize this problem, commercial supplies of THF are often stabilized with ] (BHT). Distillation of THF to dryness is unsafe because the explosive peroxides can concentrate in the residue.
			==Related compounds==
			===Tetrahydrofurans===
			], an ].]]
			] (brand name: Halaven), a commercial THF-containing ].]]
			The tetrahydrofuran ring is found in diverse natural products including ]s, ]s, and ] natural products.<ref>{{cite journal |doi=10.1021/cr3004778|title=Tetrahydrofuran-Containing Macrolides: A Fascinating Gift from the Deep Sea|year=2013|last1=Lorente|first1=Adriana|last2=Lamariano-Merketegi|first2=Janire|last3=Albericio|first3=Fernando|last4=Álvarez|first4=Mercedes|journal=Chemical Reviews|volume=113|issue=7|pages=4567–4610|pmid=23506053}}</ref> Diverse methodology has been developed for the synthesis of substituted THFs.<ref>{{cite journal |doi=10.1016/j.tet.2006.08.105|title=Recent advances in the stereoselective synthesis of tetrahydrofurans|year=2007|last1=Wolfe|first1=John P.|last2=Hay|first2=Michael B.|journal=Tetrahedron|volume=63|issue=2|pages=261–290|pmid=18180807|pmc=1826827}}</ref>
			===Oxolanes===
			Tetrahydrofuran is one of the class of pentic cyclic ethers called ''oxolanes''. There are seven possible structures, namely,<ref>{{Cite journal|url=https://onlinelibrary.wiley.com/doi/abs/10.1002/ijch.198300010|doi = 10.1002/ijch.198300010|title = Theoretical Determination of Molecular Structure and Conformation. XI. The Puckering of Oxolanes|year = 1983|last1 = Cremer|first1 = Dieter|journal = Israel Journal of Chemistry|volume = 23|pages = 72–84}}</ref>
			* Monoxolane, the root of the group, synonymous with ''tetrahydrofuran''
			* ]
			* ]
			* 1,2,4-trioxolane
			* 1,2,3-trioxolane
			* tetroxolane
			* pentoxolane
	==See also==		==See also==
			{{commonscat|Tetrahydrofuran}}
	* ]
	* ]		* ]
			* ]
	* ]		* ]
			* Other cyclic ethers: ] ({{chem|C|2|H|4|O}}), ] ({{chem|C|3|H|6|O}}), ] ({{chem|C|5|H|10|O}})
	==References==		==References==
	{{reflist|2}}		{{Reflist|30em}}
	==General reference==		==General reference==
	* Loudon, G. Mark. ''Organic Chemistry 4th ed.'' New York: ]. 2002. pg 318.		* {{cite book |last=Loudon |first=G. Mark |title=Organic Chemistry |edition=4th |location=New York |publisher=] |date=2002 |page= |isbn=978-0-9815194-3-2 |url=https://archive.org/details/organicchemistry0000loud/page/318 }}
	==External links==		==External links==
	*		*
	*		*
			* {{Webarchive|url=https://web.archive.org/web/20170502181253/https://www.osha.gov/dts/chemicalsampling/data/CH_271000.html |date=2017-05-02 }}
	*
			* {{cite web| url=http://www.sigmaaldrich.com/Area_of_Interest/Research_Essentials/Solvents/Key_Resources/Me_THF.html| title=2-Methyltetrahydrofuran, An alternative to Tetrahydrofuran and Dichloromethane|publisher=Sigma-Aldrich|access-date=2007-05-23}}
	*
			{{Authority control}}
	*
	* {{cite web| url=http://www.sigmaaldrich.com/Area_of_Interest/Research_Essentials/Solvents/Key_Resources/Me_THF.html| title=2-Methyltetrahydrofuran, An alternative to Tetrahydrofuran and Dichloromethane|publisher=Sigma-Aldrich|accessdate=2007-05-23}}
	]		]
	]		]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]