All Photos(1)

360589

Sigma-Aldrich

Tetrahydrofuran

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

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

Quality Level

grade

ACS reagent

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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
  • Grignard
  • Organometallic compounds
  • Reformatsky
  • Lithiation
  • Hydride reduction
  • Metal-catalyzed coupling (Heck, Stile, Suzuki)
  • 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

Packaging

500, 6×500 mL in glass bottle
1, 6×1, 2.5, 4, 4×4 L in glass bottle
18, 200 L in steel drum

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

Supplementary Hazards

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

-6.2 °F - closed cup

Flash Point(C)

-21.2 °C - closed cup

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.

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

    A significant number of laboratory solvents can undergo autoxidation under normal storage conditions to form unstable and potentially dangerous peroxide by-products. Molecular structure is the primary factor relating to a material’s potential for hazardous peroxide formation.  It is important to understand the stability of materials in use and if unclear, consult Sigma-Aldrich Technical Support, techserv@sial.com.

  12. What are some of the preservatives used in the most common ethers and chlorinated solvents and why are they added?

    Certain solvents will degrade over time requiring special handling and storage considerations. In addition, the products of certain degradation processes pose a potential safety risk if present at sufficiently high levels. For these types of materials, small amounts of stabilizing chemicals are added to slow down or stop material degradation.

  13. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  14. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  15. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Mg2Si nanoparticle synthesis for high pressure hydrogenation.
Chaudhary AL, et al.
The Journal of Physical Chemistry C, 118(2), 1240-1247 (2014)
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
Practical Synthesis of Di-tert-Butyl-Phosphinoferrocene.
Busacca CA, et al.
Organic Syntheses, 90, 316-326 (2013)
Synthesis of NiO/TiO2 using amphiphilic diblock copolymer brushes (PMMA-b-PAA) by reversible addition fragmentation chain-transfer poltmerization.
Hojjati B and Charpentier PA.
Polymer Reviews, 50(2), 418-418 (2009)
P T Clayton et al.
The Journal of clinical investigation, 79(4), 1031-1038 (1987-04-01)
Urinary bile acids from a 3-mo-old boy with cholestatic jaundice were analyzed by ion exchange chromatography and gas chromatography-mass spectrometry (GC-MS). This suggested the presence of labile sulfated cholenoic acids with an allylic hydroxyl group, a conclusion supported by analysis

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