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Sigma-Aldrich

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:
109-99-9
Molecular Weight:
72.11
Beilstein:
102391
EC Number:
203-726-8
MDL number:
MFCD00005356
UNSPSC Code:
12191501
PubChem Substance ID:
329755267
NACRES:
NA.21
grade:
ACS reagent
Assay:
≥99.0%
technique(s):
HPLC: suitable
bp:
65-67 °C (lit.)
vapor pressure:
114 mmHg ( 15 °C)
143 mmHg ( 20 °C)
Pricing and availability is not currently available.

Product Name

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

grade

ACS reagent

Quality Level

200

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.

Other Notes

Go to our Greener Alternative-2-Methyl Tetrahydrofuran - 155810

Go to our Greener Alternative-Cyclopentyl methylether - 675989

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

EUH019

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

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB2072
SDBB0468
STBL3723
MKCV4998
SHBR8034

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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)
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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

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    1. 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.

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

    1 answer

    1. 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.

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

    1 answer

    1. Email us at [email protected] or visit Sigma-Aldrich Fine Chemicals for development and manufacturing-scale inquiries: [email protected]

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

    1 answer

    1. 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.

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

    1 answer

    1. 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.

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  8. What are the options for drying solvents?

    1 answer

    1. 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.

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

    1 answer

    1. 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, [email protected].

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