Tetrahydrofuran

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Tetrahydrofuran
Image:Tetrahydrofuran-2D-skeletal.png Image:Tetrahydrofuran-3D-vdW.png
General
Systematic name	Tetrahydrofuran
Other names	THF, hydrofuran, oxolane, oxacyclopentane, furanidine
Molecular formula	C₄H₈O
SMILES	C1CCCO1
Molar mass	72.11 g/mol
Appearance	colorless liquid
CAS number	[109-99-9]
Properties
Density and phase	0.886 g/cm³, liquid
Solubility in water	Miscible
Melting point	-108.4 °C (164.75 K)
Boiling point	66 °C (339.15 K)
Viscosity	0.48 cP at 25 °C
Structure
Molecular shape	envelope
Dipole moment	1.63 D (gas)
Hazards
MSDS	External MSDS
EU classification	Flammable (F) Irritant (Xi)
NFPA 704	Image:NFPA 704.svg 3 2 1
R-phrases	R11, R19, R36/37
S-phrases	S16, S29, S33
Flash point	-14 °C
RTECS number	LU5950000
Supplementary data page
Structure and properties	n, ε_r, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Related heterocycles	Furan Pyrrolidine Dioxane
Related compounds	Diethyl ether
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

For other uses of THF, see THF (disambiguation)

Tetrahydrofuran is a heterocyclic organic compound. It is a clear, low-viscosity liquid with a diethyl ether-like smell. It is one of the most polar ethers and is used as a solvent of intermediate polarity in chemical reactions. THF is an aprotic, electron donating solvent with a dielectric constant of 7.6. THF is the fully hydrogenated analog of the aromatic compound furan.

1 Uses
2 Precautions
3 External links
4 References
5 See also
6 External links

[edit] Uses

THF is a moderately polar, aprotic solvent. It is able to dissolve a wide range of compounds.

Diethyl ether can often be substituted with THF, especially when a higher-boiling solvent is required. Thus THF, like diethyl ether, is often used for hydroborations used to synthesize primary alcohols. Both ethers have an oxygen atom which can coordinate to the electron-deficient boron atom, forming an adduct. Similarly, THF or diethyl ether are often used as solvents for Grignard reagents because of the oxygen atom's ability to coordinate to the magnesium atom on the Grignard reagent.

THF is often used in polymer science. For example, it can be used to dissolve rubber prior to determining its molecular mass using gel permeation chromatography. It is often used industrially to degrease metal parts.

[edit] Precautions

THF tends to form peroxides on storage. As a result, THF should not be distilled to dryness, which can leave a residue of highly-explosive peroxides. Commercial THF is therefore often inhibited with BHT. Alternatively, THF can be stored in air-tight bottles in the dark over sodium hydroxide.