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676764

Sigma-Aldrich

Tetrahydrofuran

ACS reagent, ≥99.0%, contains 250 ppm BHT as inhibitor

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Synonym(s):
Butylene oxide, Oxolane, Tetramethylene oxide
Empirical Formula (Hill Notation):
C4H8O
CAS Number:
Molecular Weight:
72.11
Beilstein/REAXYS Number:
102391
EC Number:
MDL number:
PubChem Substance ID:

grade

ACS reagent

Quality Level

vapor density

2.5 (vs air)

vapor pressure

114 mmHg ( 15 °C)
143 mmHg ( 20 °C)

assay

≥99.0%

form

liquid

autoignition temp.

610 °F

contains

250 ppm BHT as inhibitor

expl. lim.

1.8-11.8 %

technique(s)

HPLC: suitable

impurities

≤0.015% peroxide (as H2O2)
≤0.05% water

evapn. residue

≤0.03%

color

APHA: ≤20

refractive index

n20/D 1.407 (lit.)

pH

~7

bp

65-67 °C (lit.)

mp

−108 °C (lit.)

density

0.889 g/mL at 25 °C (lit.)

SMILES string

C1CCOC1

InChI

1S/C4H8O/c1-2-4-5-3-1/h1-4H2

InChI key

WYURNTSHIVDZCO-UHFFFAOYSA-N

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1 of 4

This Item
36058987368186562
vibrant-m

676764

Tetrahydrofuran

Essential Grade
vibrant-m

360589

Tetrahydrofuran

-
vibrant-m

87368

Tetrahydrofuran

Essential Grade
vibrant-m

186562

Tetrahydrofuran

-
assay

≥99.0%

assay

≥99.0%

assay

≥99.9%

assay

≥99.9%

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

form

liquid

form

liquid

form

liquid

form

liquid

technique(s)

HPLC: suitable

technique(s)

HPLC: suitable

technique(s)

solid phase extraction (SPE): suitable

technique(s)

-

refractive index

n20/D 1.407 (lit.)

refractive index

n20/D 1.407 (lit.)

refractive index

n20/D 1.407 (lit.)

refractive index

n20/D 1.407 (lit.)

General description

Tetrahydrofuran (THF) is a heterocyclic compound (cyclic ether). It is colorless, has low viscosity, and good solubility in a wide range of solvents. It is widely used as a solvent in organic synthesis, being very popular in reactions with organometallic compounds and Grignard reagents. Due to organic peroxides formation on long term storage, THF is usually stabilized by adding butylated hydroxytoluene (BHT). BHT removes the free radicals required for the peroxide formation.

Application

Tetrahydrofuran (THF) is used as a solvent in the following processes:
  • Organic synthesis
a) Grignard
b) Organometallic compounds
c) Reformatsky
d) Lithiation
e) Hydride reduction
f) Metal-catalyzed coupling (Heck, Stile, Suzuki)
g) Lewis acid mediated reactions
  • Crystallization
  • Polymerization. Ex. RAFT (Reversible Addition-Fragmentation Chain Transfer) polymerization of p-acetoxystyrene
  • Coatings
  • As an O-donor ligand to form coordination complexes
  • As mobile phase solvent in high-performance liquid chromatography

Features and Benefits

ACS solvents meet or exceed the high standards of the American Chemical Society (ACS) ,with test specifications that are specialized to every compound. According to the American Chemical Society, ACS reagent grade implies that it is a substance of sufficient purity to be used in most chemical analyses or reactions.

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2

supp_hazards

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

-6.2 °F - closed cup

flash_point_c

-21.2 °C - closed cup


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Oxidation of tetrahydrofuran to butyrolactone catalyzed by iron-containing clay.
Ausavasukhi A and Sooknoi T.
Green Chemistry, 17(1), 435-441 (2015)
An efficient and economical process for lignin depolymerization in biomass-derived solvent tetrahydrofuran.
Long J, et al.
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Novel Diacetylinic Aryloxysilane Polymers: A New Thermally Cross-Linkable High Temperature Polymer System.
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1,3 Dioxolane versus tetrahydrofuran as promoters for CO2-hydrate formation: Thermodynamics properties, and kinetics in presence of sodium dodecyl sulfate.
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