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401757 Sigma-Aldrich

Tetrahydrofuran

anhydrous, ≥99.9%, inhibitor-free

Synonym: THF

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Properties

Related Categories Alternative Energy, Anhydrous, Anhydrous Solvents, Electrolytes, Lithium-Ion Batteries,
grade   anhydrous
vapor density   2.5 (vs air)
vapor pressure   114 mmHg ( 15 °C)
  143 mmHg ( 20 °C)
InChI Key   WYURNTSHIVDZCO-UHFFFAOYSA-N
assay   ≥99.9%
autoignition temp.   610 °F
expl. lim.   11.8 %
impurities   ≤20 ppm peroxide (as H2O2)
  <0.002% water
  <0.005% water (100 mL pkg)
evapn. residue   <0.0005%
refractive index   n20/D 1.407(lit.)
bp   65-67 °C(lit.)
mp   −108 °C(lit.)
solubility   H2O: soluble
density   0.889 g/mL at 25 °C(lit.)

Description

Other Notes

Pure-Pac® II containers require the Micromatic MacroValve coupler for dispensing solvents, Z560723.

Packaging

1, 6×1, 2, 4×2 L in Sure/Seal™

18 L in Pure-Pac™ 1

20, 50 L in Pure-Pac™ 2

56 L in Pure-Pac™ 1

View returnable container options.

100, 12×100 mL in Sure/Seal™

200 L in Pure-Pac™ 2

Application

Tetrahydrofuran was used as a solvent in the formation of diacetylinic polymers.
It may be used in the following processes:
• Formation of butyrolactone (BTL) by green oxidation method.
• Aqueous THF solution to modify the polystyrene surface by swelling process.
• As a solvent for lignin depolymerization to isolate phenolic monomer.

General description

Tetrahydrofuran (THF) is a saturated cyclic ether with a potential use as a biofuel. Its combustion studies have been investigated. Reports suggest that it is a better promoter than 1,3 dioxolane for CO2-hydrate formation.

Legal Information

Pure-Pac is a registered trademark of Sigma-Aldrich Co. LLC

Price and Availability


LC-MS Grade Solvents and Reagents

Bulk Chemicals
Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Supplemental Hazard Statements 
May form explosive peroxides.
RIDADR 
UN 2056 3 / PGII
WGK Germany 
1
RTECS 
LU5950000
Flash Point(F) 
1.4 °F
Flash Point(C) 
-17 °C

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

A New Palladium Precatalyst Allows for the Fast Suzuki-Miyaura Coupling Reactions of Unstable Polyfluorophenyl and 2-Heteroaryl Boronic Acids

A method for the Pd-catalyzed coupling of 2-aminothiazole derivatives with aryl bromides and triflates is described. Significantly, for this class of nucleophiles, the coupling exhibits a broad subst...
Keywords: Catalysis, Chromatography

Catalytic Direct Cross-Coupling of Organolithium Compounds with Aryl Chlorides

Complex, hindered biaryls have been prepared at temperatures ranging from 1�C to room temperature, or with gentle heating. The Pd-PEPPSI-IPent catalyst nicely couples starting materials containing ac...
Keywords: Chromatography, Flash chromatography

Cross Coupling Reactions of Chiral Secondary Organoboronic Esters With Retention of Configuration-

We describe a systematic study of the scope and relationship between ligand structure and activity for a highly efficient and selective class of catalysts containing sterically hindered chelating alk...
Keywords: Aminations, Gas chromatography, Ligands

Design and preparation of new palladium precatalysts for C-C and C-N cross-coupling reactions

Good to excellent yields�of aryl trifluoromethyl sulfides, which are an important class of compounds in both the pharmaceutical and agrochemical areas, can be achieved under mild conditions by the Pd...
Keywords: Agrochemicals, Catalysis, Pharmaceutical

Electrolyte Reagents for Lithium-Ion Batteries

Introduction Battery grade electrolytes Solvents and additives Preparation of customized battery grade electrolyte solutions Materials References
Dr. Koji Abe
Advanced Energy Materials R&D Center, Chemicals Company, UBE Industries, Ltd.
Keywords: Acid value, Industries, Solvents

Highly Selective Palladium-Catalyzed Cross-Coupling of Secondary Alkylzinc Reagents with Heteroaryl Halides | Materials & Procedure

The highly selective palladium-catalyzed Negishi coupling of secondary alkylzinc reagents with heteroaryl halides is described. The development of atseries of biarylphosphine ligands has led to the i...
Keywords: Catalysis, Eliminations, Gas chromatography, Ligands, Negishi Coupling, Nuclear magnetic resonance spectroscopy, Oxidative additions, Reductive eliminations

Mild Palladium-Catalyzed Cyanation of (Hetero)aryl Halides and Triflates in Aqueous Media-

The development of a novel Pd-catalyzed synthesis of (hetero)aromatic nitriles from the corresponding aryl chlorides and potassium hexacyanoferrate(II) is described. This novel protocol avoids the us...
Keywords: Catalysis, Chromatography, Column chromatography, Gas chromatography, Ligands, Solvents

Mild and General Conditions for Negishi Cross-Coupling Enabled by the Use of Palladacycle Precatalysts

A wide range of biaryls were synthesized by palladium-catalyzed Negishi cross-couplings at ambient temperature or with low catalyst loading. This protocol features the use of a recently reported amin...
Keywords: Catalysis, Cross couplings

Negishi cross-coupling of secondary alkylzinc halides with aryl/heteroaryl halides using Pd-PEPPSI-IPent

Over the past two decades, considerable attention has been given to the development of new ligands for the palladium-catalyzed arylation of amines and related NH-containing substrates (i.e. Buchwald-...
Keywords: Aminations, Arylations, Buchwald-Hartwig amination, Catalysis, Chromatography, Column chromatography, Cross couplings, Gas chromatography, Hydroaminations, Ligands, Thin layer chromatography

Palladium-catalyzed inter- and intramolecular cross-coupling reactions of B-alkyl-9-borabicyclo[3.3.1]nonane derivatives with 1-halo-1-alkenes or haloarenes. Syntheses of functionalized alkenes, arenes, and cycloalkenes via a hydroboration-coupling sequence

The cross-coupling reaction of B-alkyl-9-borabicyclo[3.3.l]nonanes (B-R-9 BBN), readily obtainable from alkenes by hydroboration, with 1-halo-1-alkenes or haloarenes in the presence of a catalytic am...
Keywords: Catalysis, Chromatography, Column chromatography, Coupling reactions, Cross couplings, Oxidations

Palladium/Tris(tert-butyl)phosphine-Catalyzed Suzuki Cross- Couplings in the Presence of Water

The Suzuki reaction is an exceptionally useful cross-coupling process that has been widely applied in synthetic chemistry, and boronic acids are, by far, the most commonly employed coupling partner. ...
Keywords: Chromatography, Column chromatography, Cross couplings, Eliminations, Oxidative additions, Suzuki reactions

Pd-PEPPSI-IPent: Low-Temperature Negishi Cross-Coupling for the Preparation of Highly Functionalized, Tetra-ortho-Substituted Biaryls-

A convenient protocol for the rapid and efficient synthesis of 3-(N-substituted) aminocoumarins is described. The synthetic route developed involves the Pd-catalyzed C-N coupling reaction from readil...
Keywords: Catalysis, Chromatography, Column chromatography, Coupling reactions, Purification

Pressure-Temperature Calculator for Solvents

*Calculations provide estimated results based on Antoine's Coefficients and their associated temperature range values. Antoine's Coefficients were obtained from the National Institute of Standards an...

Regioselective Cross-Coupling of Allylboronic Acid Pinacol Ester Derivatives with Aryl Halides via Pd-PEPPSI-IPent-

Palladium-catalyzed direct cross-coupling of aryl chlorides with a wide range of (hetero)aryl lithium compounds is reported. The use of Pd-PEPPSI-IPent or Pd2(dba)3/XPhos as the catalyst allows for t...
Keywords: Catalysis, Chromatography, Column chromatography, Cross couplings, Evaporation

Reversed-Polarity Synthesis of Diaryl Ketones through Palladium- Catalyzed Direct Arylation of 2-Aryl-1,3-dithianes

The title reaction leads to satisfactory yields of dihydrodibenzoazepines�1?a�from norbornene. The dibenzoazepines�2�can also be accessed from compounds of type�1?b�when norbornadiene is used as a re...
Keywords: Chromatography, Column chromatography

Room-Temperature Alkyl-Alkyl Suzuki Cross-Coupling of Alkyl Bromides that Possess -- Hydrogens

The trifluoromethyl group can dramatically influence the properties of organic molecules, thereby increasing their applicability as pharmaceuticals, agrochemicals, or building blocks for organic mate...
Keywords: Agrochemicals, Building blocks, Catalysis, Pharmaceutical, transformation

The First Negishi Cross-Coupling Reaction of Two Alkyl Centers Utilizing a Pd-N-Heterocyclic Carbene (NHC) Catalyst

The development of an NHC-based system capable of cross-coupling sp3-sp3 centers in high yield has been a long-standing challenge. This communication describes the use of a Pd-NHC catalytic system th...
Keywords: Catalysis, Chromatography, Cross couplings, Flash chromatography

Related Content

Pressure-Temperature Nomograph Interactive Tool

The Pressure-Temperature Nomograph tool is an application of the Clausius-Clapeyron Equation, which assumes the heat of vaporization is a constant over a pressure range. Antoine´s Equation gets aroun...
Keywords: Evaporation, Vaporization

Properties of Solvents Table

a. Gant, R., LC/GC 10(7), 515 (1992) 1. At 20 °C 2. At 20 °C +/- 5 °C relative to water at 4 °C 3. At 10mmHg pressure 4. At l=589.32nm
Keywords: Gas chromatography, High performance liquid chromatography

Peer-Reviewed Papers
15

References

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Z560723 Micromatic MacroValve coupler for returnable containers, with 4F key Pure-Pac® II containers require the Micromatic Macrovalve for dispensing solvents.

suggested gloves for splash protection

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