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Sigma-Aldrich

Tetrahydrofuran

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

Synonym(s):

THF, Butylene oxide, Oxolane, Tetramethylene oxide

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About This Item

Empirical Formula (Hill Notation):
C4H8O
CAS Number:
109-99-9
Molecular Weight:
72.11
Beilstein/REAXYS Number:
102391
EC Number:
203-726-8
MDL number:
MFCD00005356
UNSPSC Code:
12191501
PubChem Substance ID:
329760651

product name

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

grade

ACS reagent

Quality Level

200

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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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.

Other Notes

Go to our Greener Alternative-2-Methyl Tetrahydrofuran - 155810

Go to our Greener Alternative-Cyclopentyl methylether - 675989

signalword

Danger

Hazard Classifications

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

supp_hazards

EUH019

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Solène I Cauët et al.
Journal of polymer science. Part A, Polymer chemistry, 48(12), 2517-2524 (2010-07-27)
The kinetics of the RAFT polymerization of p-acetoxystyrene using a trithiocarbonate chain transfer agent, S-1-dodecyl-S'-(α,α'-dimethyl-α″-acetic acid)trithiocarbonate, DDMAT, was investigated. Parameters including temperature, percentage initiator, concentration, monomer-to-chain transfer agent ratio and solvent were varied and their impact on the rate of
1,3 Dioxolane versus tetrahydrofuran as promoters for CO2-hydrate formation: Thermodynamics properties, and kinetics in presence of sodium dodecyl sulfate.
Torre JP, et al.
Chemical Engineering Science, 126, 688-697 (2015)
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.
Bioresource Technology, 154, 10-17 (2014)
Novel Diacetylinic Aryloxysilane Polymers: A New Thermally Cross-Linkable High Temperature Polymer System.
Drake K, et al.
Macromolecules, 46(11), 4370-4377 (2013)
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