Tetrahydrofuran

"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
3D model (JSmol)
Abbreviations THF
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.389 Edit this at Wikidata
RTECS number
  • LU5950000
UNII
  • 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
  • C1CCOC1
Properties
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]
Miscible
Vapor pressure 132 mmHg at 20 °C[2]
1.4073 at 20 °C[3]
Viscosity 0.48 cP at 25 °C
Structure
Envelope
1.63 D (gas)
Hazards
GHS labelling:
GHS02: Flammable GHS07: Exclamation mark GHS08: Health hazard[5]
Danger
H225, H302, H319, H335, H351[5]
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):
  • 1650 mg/kg (rat, oral)
  • 2300 mg/kg (mouse, oral)
  • 2300 mg/kg (guinea pig, oral)[6]
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 ?)

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).