Tetrahydrofuran
General
Systematic name	Tetrahydrofuran
Other names	THF, 1,4-epoxybutane, butylene oxide, cyclotetramethylene oxide, oxacyclopentane, diethylene oxide, oxolane, furanidine, hydrofuran, tetra-methylene oxide
Molecular formula	C4H8O
SMILES	C1CCCO1
Molar mass	72.11 g/mol
Appearance	colorless liquid
CAS number	[109-99-9]
Properties
Density and phase	0.8892 g/cm3 @ 20 °C, 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 File history File links Download high-resolution version (766x818, 9 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Ether Tetrahydrofuran ... Image File history File links Download high-resolution version (1100x1025, 214 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Tetrahydrofuran ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... Density, or volumic mass (ISO 31), is a measure of mass per volume. ... In the physical sciences, a phase is a set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (i. ... It has been suggested that this article or section be merged with Solution. ... This article describes water from a scientific and technical perspective. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ... The pitch drop experiment at the University of Queensland. ... four sp³ orbitals three sp² orbitals In chemistry, hybridisation or hybridization (see also spelling differences) is the concept of mixing atomic orbitals to form new hybrid orbitals suitable for the qualitative description of atomic bonding properties. ... // The Earths magnetic field, which is approximately a dipole. ... The debye (symbol: D) is a non-SI and non-CGS unit of electrical dipole moment. ... A material safety data sheet or MSDS is a form containing data regarding the properties of a particular substance. ... Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws, regulations and administrative provisions relating to the classification, packaging and labelling of dangerous substances (as amended) is the main source of European Union law concerning chemical safety. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links NFPA_704. ... 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, εr, 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. R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture with air. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... The refractive index (or index of refraction) of a material is the factor by which the phase velocity of electromagnetic radiation is slowed in that material, relative to its velocity in a vacuum. ... The dielectric constant εr (represented as or K in some cases) is defined as the ratio: where εs is the static permittivity of the material in question, and ε0 is the vacuum permittivity. ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... IR spectrum of a thin film of liquid ethanol. ... Nuclear Magnetic Resonance Spectroscopy most commonly known as NMR Spectroscopy is the name given to the technique which exploits the magnetic properties of nuclei. ... Basic schematic of a mass spectrometer Mass spectrometry (also known as mass spectroscopy (deprecated)[1] or in common speech mass-spec) is an analytical technique used to measure the mass-to-charge ratio of ions. ... Heterocycles are organic chemical structures containing non-carbon elements. ... Furan, also known as furane and furfuran, is an aromatic heterocyclic organic compound, produced when wood, especially pine-wood, is distilled. ... Flash point 3 °C R/S statement R: 11 20/21/22 35 S: 16 26 28 36/37 45 RTECS number UX9650000 Related compounds Related compounds pyrrole piperidine Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and... 1,4-Dioxane, often just called dioxane, is a clear, colorless organic compound which is a liquid at room temperature and pressure. ... Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic smell. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... THF may refer to: Tetrahydrofuran Tetrahydrofolate Trust House Forte, a UK-based hotel and catering group THF, the IATA airport code for Tempelhof International Airport Category: ... Pyridine a simple heterocyclic compound Heterocyclic compounds are organic compounds which contain a ring structure containing atoms in addition to carbon, such as sulfur, oxygen or nitrogen, as part of the ring. ... Benzene is the simplest of the arenes, a family of organic compounds An organic compound is any member of a large class of chemical compounds whose molecules contain carbon and hydrogen; therefore, carbides, carbonates, carbon oxides and elementary carbon are not organic (see below for more on the definition controversy... The pitch drop experiment at the University of Queensland. ... Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic smell. ... A commonly-used example of a polar compound is water (H2O). ... Ether is the general name for a class of chemical compounds which contain an ether group — an oxygen atom connected to two (substituted) alkyl groups. ... For other uses, see Solvent (disambiguation). ... A chemical reaction occurs when vapours of hydrogen chloride and ammonia meet to form a cloud of a new substance, ammonium chloride Chemical reaction is a process that results in the interconversion of chemical substances [1]. The substance or substances initially involved in a chemical reaction are called reactants. ... In chemistry any solvent that carries hydrogen attached to oxygen as in a hydroxyl group, nitrogen as in a amine group, or, more generally, any molecular solvent which contains dissociable H+, such as hydrogen fluoride, is called a protic solvent. ... An electron donor is a compound that gives up or donates an electron during cellular respiration, resulting in the release of energy. ... The dielectric constant εr (represented as or K in some cases) is defined as the ratio: where εs is the static permittivity of the material in question, and ε0 is the vacuum permittivity. ... Hydrogenation is a chemical reaction in which unsaturated bonds between carbon atoms are reduced by attachment of a hydrogen atom to each carbon. ... In chemistry, an aromatic molecule is one in which electrons are free to cycle around circular arrangements of atoms, which are alternately singly and doubly bonded to one another. ... Furan, also known as furane and furfuran, is an aromatic heterocyclic organic compound, produced when wood, especially pine-wood, is distilled. ...

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. Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic smell. ... A hydroboration-oxidation reaction is an organic chemistry reaction used to add a hydroxyl group (OH-) and a hydrogen cation (H+) to an alkene via anti-Markovnikov addition. ... Wikipedia does not yet have an article with this exact name. ... A Grignard Reagent is an alkyl- or aryl- magnesium halide. ...

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. Latex being collected from a tapped rubber tree Rubber is an elastic hydrocarbon polymer which occurs as a milky colloidal suspension (known as latex) in the sap of several varieties of plants. ... Gel permeation chromatography (GPC) also known as size exclusion chromatography (SEC) is a chromatographic method in which molecules are separated based on their size. ...

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. Organic peroxides are organic molecules containing the peroxide functional group ROOR If the R is hydrogen, the compound is called an organic hydroperoxide or a peroxy acid. ... Flash point 127 °C R/S statement R: 22-36 37 38 S: 26-36 RTECS number GO7875000 Related compounds Related compounds butylated hydroxyanisole Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references BHT is the common... Sodium hydroxide (NaOH), also known as lye or caustic soda, is a caustic metallic base. ...

External links

• International Chemical Safety Card 0578
• NIOSH Pocket Guide to Chemical Hazards

• THF usage on Organic Syntheses
• THF info
• U.S. OSHA info on THF

References

• Loudon, G. Mark. Organic Chemistry 4th ed. New York: Oxford University Press. 2002. pg 318.

See also

• The Trapp mixture extends the temperature range applicability of THF as a solvent.

The Trapp mixture is a specific mixture of organic solvents for chemical reactions taking place at very low temperatures. ...

External links

• Links to external chemical sources.