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178810

Sigma-Aldrich

Tetrahydrofuran

≥99.0%, contains 250 ppm BHT as inhibitor, ReagentPlus®

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/REAXYS Number:
102391
EC Number:
203-726-8
MDL number:
MFCD00005356
UNSPSC Code:
12191501
PubChem Substance ID:
329751576
NACRES:
NA.21

product name

Tetrahydrofuran, ReagentPlus®, ≥99.0%, contains 250 ppm BHT as inhibitor

vapor density

2.5 (vs air)

Quality Level

100

vapor pressure

114 mmHg ( 15 °C)
143 mmHg ( 20 °C)

product line

ReagentPlus®

assay

≥99.0%

form

liquid

autoignition temp.

610 °F

contains

250 ppm BHT as inhibitor

expl. lim.

1.8-11.8 %

refractive index

n20/D 1.407 (lit.)

pH

~7

bp

65-67 °C (lit.)

mp

−108 °C (lit.)

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 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. THF constitutes the key fragment of various natural products (polyether antibiotics). THF can form a double hydrate with hydrogen sulfide. Crystal structure of this double hydrate has been investigated by three-dimensional single-crystal studies. Butane-1,4-diol is formed as an intermediate during the synthesis of THF. Hot THF is useful for the dissolution of polyvinylidene chloride (PVDV).

Application

Tetrahydrofuran may be used for the dissolution of poly-ε-caprolactone (PCL) and 1,3-diaminopentane, during the preparation of poly-ε-caprolactone (PCL)-hydroxyapatite (HA) scaffolds and acrylate-terminated poly(5-amino-1-pentanol-co-1,4-butanediol diacrylate) (C32)- 1,3-diaminopentane (117) polymer, respectively.

Other Notes

For information on tetrahydrofuran miscibility, please visit the following link:
Tetrahydrofuran Miscibility/Immiscibility Table

Greener alternatives are available for many THF applications, 2-Methyltetrahydrofuran (155810) and Cyclopentyl methyl ether (675989)

Read more about THF alternatives:
2-Methyltetrahydroun (2-MeTHF): A biomass-Derived solvent with Broad Applications in Organic Chemistry

The toxicological assessment of cyclopentyl methyl ether (CPME) as a green solvent

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

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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

supp_hazards

EUH019

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

-6.2 °F - closed cup

flash_point_c

-21.2 °C - closed cup

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Vittorio Pace et al.
ChemSusChem, 5(8), 1369-1379 (2012-08-14)
2-Methyl-tetrahydrofuran (2-MeTHF) can be derived from renewable resources (e.g., furfural or levulinic acid) and is a promising alternative solvent in the search for environmentally benign synthesis strategies. Its physical and chemical properties, such as its low miscibility with water, boiling
Kiyoshi Watanabe
Molecules (Basel, Switzerland), 18(3), 3183-3194 (2013-03-13)
Cyclopentyl methyl ether (CPME) has been used in chemical synthesis as an alternative to hazardous solvents. According to some earlier investigation by others, CPME has low acute or subchronic toxicity with moderate irritation and negative mutagenicity and negative skin sensitization
Todd J Harris et al.
Biomaterials, 31(5), 998-1006 (2009-10-24)
The use of biomaterials for gene delivery can potentially avoid many of the safety concerns with viral gene delivery. However, the efficacy of polymeric gene delivery methods is low, particularly in vivo. One significant concern is that the interior and
Synthetic routes to tetrahydrofuran, tetrahydropyran, and spiroketal units of polyether antibiotics and a survey of spiroketals of other natural products.
Boivin TLB.
Tetrahedron, 43(15), 3309-3362 (1987)
Haiying Yu et al.
Biomaterials, 30(4), 508-517 (2008-11-01)
Natural bone growth greatly depends on the precedent vascular network that supplies oxygen and essential nutrients and removes metabolites. Likewise, it is crucial for tissue-engineered bone to establish a vascular network that temporally precedes new bone formation, and spatially originates
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