186562

Sigma-Aldrich

Tetrahydrofuran

anhydrous, contains 250 ppm BHT as inhibitor, ≥99.9%

Synonym(s):
Tetramethylene oxide, THF, Oxolane, Butylene oxide
Empirical Formula (Hill Notation):
C4H8O
CAS Number:
Molecular Weight:
72.11
Beilstein/REAXYS Number:
102391
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

Quality Level

grade

anhydrous

vapor density

2.5 (vs air)

vapor pressure

114 mmHg ( 15 °C)
143 mmHg ( 20 °C)

assay

≥99.9%

form

liquid

autoignition temp.

610 °F

contains

250 ppm BHT as inhibitor

expl. lim.

1.8-11.8 %

impurities

≤0.005% peroxides (as H2O2)
<0.002% water (All units except 100 mL)
<0.005% water (100 mL pkg)

refractive index

n20/D 1.407 (lit.)

pH

~7

bp

65-67 °C (lit.)

mp

−108 °C (lit.)

solubility

H2O: 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

Looking for similar products? Visit Product Comparison Guide

Related Categories

General description

Tetrahydrofuran (THF) is a saturated cyclic ether mainly used as an organic solvent. On long term storage it forms organic peroxides. This process can be suppressed by adding butylated hydroxytoluene (BHT) as a stabilizer. BHT removes the free radicals required for the peroxide formation. It constitutes the key fragment of various natural products (polyether antibiotics). THF forms double hydrate with hydrogen sulfide, crystal structure of this double hydrate has been investigated by three-dimensional single-crystal studies.

Application

Dry tetrahydrofuran (THF) has been used in the synthesis of dichloro{bis[1,1′,1′′-(phosphinetriyl)tripiperidine]}palladium [(P(NC5H10)3)2Pd(Cl)2], which is widely used in the Heck reaction as a catalyst. It has been employed in the reaction medium of the Heck cross-coupling reaction of various aryl bromides and olefins.

Packaging

50, 200 L in Pure-Pac™ 2
1, 6×1, 2, 4×2 L in Sure/Seal™
208 L in steel drum
100, 12×100 mL in Sure/Seal™
18 L in Pure-Pac™ 1

Other Notes

Greener alternatives are available for many THF applications, 2-Methyltetrahydrofuran (414247) and Cyclopentyl methyl ether (675970)

Signal Word

Danger

hazcat

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

Supp Hazards

EUH019

storage_class_code

3 - Flammable liquids

WGK Germany

WGK 1

Flash Point(F)

-6.2 °F - closed cup

Flash Point(C)

-21.2 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. Who do I contact about larger solvent volume needs?

    Email us at labessentials@sial.com or visit Sigma-Aldrich Fine Chemicals for development and manufacturing-scale inquiries: safcglobal@sial.com

  4. How do I know what packaging options are available for a solvent?

    The Solvent Center gives you the ability to review all the specifications associated with our solvent packaging. This includes physical dimensions, closure types, dispensing methods, UN/DOT Rating as well as solvent compatibility. Visit the Solvent Center.

  5. Who do I contact if I need a solvent blend, which you do not carry?

    Email us at labessentials@sial.com. For a complete listing of all our Solvent blends, visit the Solvent Center

  6. The dispensing of solvents provides some challenges due to the number of container options available. What dispensing options are available for each container?

    The Sigma-Aldrich Solvent Center provides numerous dispensing options for each container type. For a complete listing of all our dispensing options, visit the Solvent Center.

  7. Which solvent grade should I be using for my application?

    Sigma-Aldrich Solvent Applications Table gives a guideline to common applications and the appropriate solvent grades.  Visit: Solvents

  8. What are the options for drying solvents? 

    Sigma-Aldrich offers a full range of high-purity solvents with extremely low water levels specifically manufactured for moisture sensitive Organic and Biotech applications.  Sigma-Aldrich also carries various drying agents such as molecular sieves, which are typically compatible with organic solvents.

  9. What apparatus do you recommend for HPLC solvent filtration?

    The Sigma-Aldrich Vacuum Filtration Assembly gives you all the components you need including: funnel top, fritted glass funnel support, filtration flask, aluminum clamp, and silicone stopper.  The Acrodisc Syringe Filters offer high quality filtration for analytical samples, certified for HPLC to ensure low extractable and available in a broad range of membranes to meet sample compatibility requirements.

  10. Can you recommend a Solvent Extractor for organics from aqueous solution?

    Solvent extractors are often used for the quantitative extraction of organics from aqueous solutions and separations in immunoassays. The MIXXOR system has been applied successfully in many laboratory solvent extraction operations and is ideal for the rapid screening of alternative solvents for specific extraction problems.

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro {bis [1, 1', 1''-(phosphinetriyl) tripiperidine]} palladium Under Mild Reaction Conditions.
Oberholzer M and Frech CM
Journal of Visualized Experiments, 85, e51444-e51444 (2014)
Mauro Niso et al.
Chembiochem : a European journal of chemical biology, 16(7), 1078-1083 (2015-03-11)
Although sigma-2 (σ2 ) receptors are still enigmatic proteins, they are promising targets for tumor treatment and diagnosis. With the aim of clarifying their role in oncology, we developed a σ2 -selective fluorescent tracer (compound 5) as a specific tool...
Nicola Antonio Colabufo et al.
Naunyn-Schmiedeberg's archives of pharmacology, 370(2), 106-113 (2004-08-24)
To establish the activity of sigma ligands at sigma1 and sigma2 receptor, we chose two tumour cell lines, the human SK-N-SH neuroblastoma and the rat C6 glioma lines, which express sigma2 receptors at a high density and sigma1 receptors in...
Maria Laura Pati et al.
BMC cancer, 17(1), 51-51 (2017-01-15)
Despite considerable efforts by scientific research, pancreatic cancer is the fourth leading cause of cancer related mortalities. Sigma-2 receptors, which are overexpressed in several tumors, represent promising targets for triggering selective pancreatic cancer cells death. We selected five differently structured...
Maria Laura Pati et al.
Pharmacological research, 117, 67-74 (2016-12-23)
A controversial relationship between sigma-2 and progesterone receptor membrane component 1 (PGRMC1) proteins, both representing promising targets for the therapy and diagnosis of tumors, exists since 2011, when the sigma-2 receptor was reported to be identical to PGRMC1. Because a...
Articles
Research and development of solid-state lithium fast-ion conductors is crucial because they can be potentially used as solid electrolytes in all-solid-state batteries, which may solve the safety and energy-density related issues of conventional lithium-ion batteries that use liquid (farmable organic) electrolytes.
Read More

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service