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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:
Molecular Weight:
72.11
Beilstein:
102391
EC Number:
MDL number:
UNSPSC Code:
12191501
PubChem Substance ID:
NACRES:
NA.21

product name

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

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.)

solubility

water: soluble

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.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

WGK

WGK 1

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Regulatory Information

危险化学品

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  11. Why do peroxides form in certain solvents and how do I test for it?

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Practical Synthesis of Di-tert-Butyl-Phosphinoferrocene.
Busacca CA, et al.
Organic Syntheses, 90, 316-326 (2013)
Luca Chiari et al.
The Journal of chemical physics, 138(7), 074301-074301 (2013-03-01)
We present total, elastic, and inelastic cross sections for positron and electron scattering from tetrahydrofuran (THF) in the energy range between 1 and 5000 eV. Total cross sections (TCS), positronium formation cross sections, the summed inelastic integral cross sections (ICS)
Tetrahydrofuran-containing macrolides: a fascinating gift from the deep sea.
Adriana Lorente et al.
Chemical reviews, 113(7), 4567-4610 (2013-03-20)

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