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Tetrahydrofuran information


"THF" redirects here. For other uses, see THF (disambiguation).
Tetrahydrofuran
Skeletal formula of tetrahydrofuran
Skeletal formula of tetrahydrofuran
Ball-and-stick model of the tetrahydrofuran molecule
Ball-and-stick model of the tetrahydrofuran molecule
Photograph of a glass bottle of tetrahydrofuran
Names
Preferred IUPAC name
Oxolane[1]
Systematic IUPAC name
1,4-Epoxybutane
1-Oxacyclopentane
Other names
Tetrahydrofuran
THF
1,4-Butylene oxide
Cyclotetramethylene oxide fraction
Furanidin
Tetra-methylene oxide, Oxolane
Identifiers
CAS Number
  • 109-99-9 checkY
3D model (JSmol)
  • Interactive image
Abbreviations THF
ChEBI
  • CHEBI:26911 ☒N
ChEMBL
  • ChEMBL276521 checkY
ChemSpider
  • 7737 checkY
ECHA InfoCard 100.003.389 Edit this at Wikidata
PubChem CID
  • 8028
RTECS number
  • LU5950000
UNII
  • 3N8FZZ6PY4 checkY
CompTox Dashboard (EPA)
  • DTXSID1021328 Edit this at Wikidata
InChI
  • InChI=1S/C4H8O/c1-2-4-5-3-1/h1-4H2 checkY
    Key: WYURNTSHIVDZCO-UHFFFAOYSA-N checkY
  • InChI=1/C4H8O/c1-2-4-5-3-1/h1-4H2
    Key: WYURNTSHIVDZCO-UHFFFAOYAI
SMILES
  • C1CCOC1
Properties
Chemical formula
 C4H8O
Molar mass 72.107 g·mol−1
Appearance Colorless liquid
Odor Ether-like[2]
Density 0.8876 g/cm3 at 20 °C, liquid [3]
Melting point −108.4 °C (−163.1 °F; 164.8 K)
Boiling point 66 °C (151 °F; 339 K)[4][3]
Solubility in water
 Miscible
Vapor pressure 132 mmHg (20 °C)[2]
Refractive index (nD)
 1.4073 (20 °C) [3]
Viscosity 0.48 cP at 25 °C
Structure
Molecular shape
 Envelope
Dipole moment
 1.63 D (gas)
Hazards
GHS labelling:
Pictograms
 GHS02: Flammable GHS07: Exclamation mark GHS08: Health hazard[5]
Signal word
 Danger
Hazard statements
 H225, H302, H319, H335, H351[5]
Precautionary statements
 P210, P280, P301+P312+P330, P305+P351+P338, P370+P378, P403+P235[5]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
3
1
Flash point −14 °C (7 °F; 259 K)
Explosive limits 2–11.8%[2]
Lethal dose or concentration (LD, LC):
LD50 (median dose)
  • 1650 mg/kg (rat, oral)
  • 2300 mg/kg (mouse, oral)
  • 2300 mg/kg (guinea pig, oral)[6]
LC50 (median concentration)
 21000 ppm (rat, 3 h)[6]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 200 ppm (590 mg/m3)[2]
REL (Recommended)
 TWA 200 ppm (590 mg/m3) ST 250 ppm (735 mg/m3)[2]
IDLH (Immediate danger)
 2000 ppm[2]
Related compounds
Related heterocycles
 Furan
Pyrrolidine
Dioxane
Related compounds
 Diethyl ether
Supplementary data page
Tetrahydrofuran (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers.[8] Being polar and having a wide liquid range, THF is a versatile solvent. It is an isomer of another solvent, butanone.

  1. ^ "New IUPAC Organic Nomenclature - Chemical Information BULLETIN" (PDF).
  2. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0602". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ 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.
  4. ^ NIST Chemistry WebBook. http://webbook.nist.gov
  5. ^ a b c Record of Tetrahydrofuran in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 2 June 2020.
  6. ^ a b "Tetrahydrofuran". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  7. ^ "New Environment Inc. - NFPA Chemicals". Newenv.com. Retrieved 2016-07-16.
  8. ^ Cite error: The named reference Ullmann was invoked but never defined (see the help page).

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Tetrahydrofuran

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Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically...

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Ether

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the reason that diethyl ether and other peroxide forming ethers like tetrahydrofuran (THF) or ethylene glycol dimethyl ether (1,2-dimethoxyethane) are avoided...

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Polytetrahydrofuran

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terminated with alcohol groups. It is produced by polymerization of tetrahydrofuran as well as 1,4-butanediol. The product is commercially available as...

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Triethylborane

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(CH3CH2)3B or (C2H5)3B, abbreviated Et3B. It is soluble in organic solvents tetrahydrofuran and hexane. Triethylborane is prepared by the reaction of trimethyl...

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Relative permittivity

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at the same time, tetrahydrofuran has its εr = 7.52 at 22 °C, but it is completely miscible with water. In the case of tetrahydrofuran, the oxygen atom...

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Imetelstat

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5R)-3-amino-5-(6-aminopurin-9-yl)tetrahydrofuran-2-yl]methoxy-hydroxy-phosphinothioyl]amino]-5-(6-aminopurin-9-yl)tetrahydrofuran-2-yl]methoxy-hydroxy-phosp...

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C4H8O

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3-Epoxybutane Ethyl vinyl ether Isobutyraldehyde 2-Methoxypropene Tetrahydrofuran This set index page lists chemical structure articles associated with...

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Properties of water

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methanol, ethanol, propanol, isopropanol, acetone, glycerol, 1,4-dioxane, tetrahydrofuran, sulfolane, acetaldehyde, dimethylformamide, dimethoxyethane, dimethyl...

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Adduct

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between the Lewis acid borane and the oxygen atom in the Lewis bases, tetrahydrofuran (THF): BH3·O(CH2)4 or diethyl ether: BH3·O(CH3CH2)2. Many Lewis acids...

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Methylamine

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primary amine. Methylamine is sold as a solution in methanol, ethanol, tetrahydrofuran, or water, or as the anhydrous gas in pressurized metal containers...

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Butanone

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used as an industrial solvent. It is an isomer of another solvent, tetrahydrofuran. Butanonyl may be produced by oxidation of 2-butanol. The dehydrogenation...

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Plastic cement

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acrylic Butanone, model cement is a thick mixture with polystyrene Tetrahydrofuran, the main solvent in PVC cement List of glues Plastic welding This...

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Reference electrode

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Acetonitrile CH3CN 0.40, 0.382 Dichloromethane CH2Cl2 0.46, 0.475 Tetrahydrofuran THF 0.56, 0.547 Dimethylformamide DMF 0.45, 0.470 Acetone (CH3)2C=O...

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Water

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methanol, ethanol, propanol, isopropanol, acetone, glycerol, 1,4-dioxane, tetrahydrofuran, sulfolane, acetaldehyde, dimethylformamide, dimethoxyethane, dimethyl...

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Furan

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enol ether and an aromatic ring. It is dissimilar vs ethers such as tetrahydrofuran. Like enol ethers, 2,5-disubstituted furans are susceptible to hydrolysis...

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Diborane

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adducts proceed rapidly to give other products. For example, borane-tetrahydrofuran, which often behaves equivalently to diborane, degrades to borate esters...

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Azeotrope tables

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Handbook of Chemistry and Physics (101 ed.). Taylor & Francis Group. "Tetrahydrofuran (THF) Storage and Handling" (PDF). BASF. Archived from the original...

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Polar aprotic solvent

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acids sulfolane C4H8SO2 286 °C ? 1.27 g/cm3 4.8 high boiling point tetrahydrofuran C4H8O 66 °C 7.6 0.887 g/cm3 1.75 polymerizes in presence of strong...

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Grignard reagent

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normally handled as solutions in solvents such as diethyl ether or tetrahydrofuran using air-free techniques. Grignard reagents are complex with the magnesium...

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Ammonia

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1000 bar. In 1994, Tsuneto et al. used lithium electrodeposition in tetrahydrofuran to synthesize ammonia at more moderate pressures with reasonable Faradaic...

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Polylactic acid

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less safe than ethyl acetate. PLA is also soluble in hot benzene, tetrahydrofuran, and dioxane. PLA objects can be fabricated by 3D printing, casting...

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Borane

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containing borane dimethylsulfide and borane–tetrahydrofuran are commercially available; in tetrahydrofuran a stabilising agent is added to prevent the...

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Bromocyclopentane

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needed] Bromocyclopentane is reacted with magnesium turnings in dry tetrahydrofuran making cyclopentyl Grignard reagent, a main precursor in the synthesis...

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Borane dimethylsulfide

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The advantages of BMS over other borane reagents, such as borane-tetrahydrofuran, are its increased stability and higher solubility. BMS is commercially...

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Aluminium chloride

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Aluminium chloride reacts with calcium and magnesium hydrides in tetrahydrofuran forming tetrahydroaluminates.[citation needed] Anhydrous aluminium...

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