178810
Tetrahydrofuran
≥99.0%, contains 200-400 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:
Molecular Weight:
72.11
UNSPSC Code:
12191501
NACRES:
NA.21
PubChem Substance ID:
EC Number:
203-726-8
Beilstein/REAXYS Number:
102391
MDL number:
Assay:
≥99.0%
Vapor pressure:
114 mmHg ( 15 °C), 143 mmHg ( 20 °C)
Quality Level
vapor pressure
114 mmHg ( 15 °C), 143 mmHg ( 20 °C)
product line
ReagentPlus®
assay
≥99.0%
form
liquid
autoignition temp.
610 °F
contains
200-400 ppm BHT as inhibitor
expl. lim.
1.8-11.8 %
dilution
(for general lab use)
pH
~7
mp
−108 °C (lit.)
density
0.889 g/mL at 25 °C (lit.)
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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
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
signalword
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
Storage Class
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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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
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
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)
Eagleson M.
Concise Encyclopedia Chemistry, 883-883 (1994)
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