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401757 Sigma-Aldrich

Tetrahydrofuran

anhydrous, ≥99.9%, inhibitor-free

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Properties

Related Categories Alternative Energy, Anhydrous, Anhydrous Solvents, Electrolytes, Materials Science,
grade   anhydrous
vapor density   2.5 (vs air)
vapor pressure   114 mmHg ( 15 °C)
  143 mmHg ( 20 °C)
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.)
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

50 L in Pure-Pac™ 2

56 L in Pure-Pac™ 1

90 L in Kilo-Lab™

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 ester 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

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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

Determination of Water Content in Tetrahydrofuran Using Karl Fischer Titration

Ethers behave similarly to hydrocarbons. They are mostly adequately soluble in methanol. Only long chain ethers require the addition of propanol or chloroform as solubilizers. Double bonds can someti...
Keywords: Solvents, Titrations

Highly Selective Palladium-Catalyzed Cross-Coupling of Secondary Alkylzinc Reagents with Heteroaryl Halides

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

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

Peer-Reviewed Papers
15

References

Set your institution to view full text papers.
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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.

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