186562

Tetrahydrofuran

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

• Synonym(s): THF, Butylene oxide, Oxolane, Tetramethylene oxide
• 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: 57647757
• NACRES: NA.21

Properties

• product name: Tetrahydrofuran, anhydrous, contains 250 ppm BHT as inhibitor, ≥99.9%
• grade: anhydrous
• Quality Level: 200
• 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

Description

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).[1] THF forms double hydrate with hydrogen sulfide, crystal structure of this double hydrate has been investigated by three-dimensional single-crystal studies.[2]

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.[3]

Packaging

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Other Notes

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

Safety Information

• Pictograms: GHS02,GHS08,GHS07
• Signal Word: Danger
• Hazard Statements: H225,H302,H319,H335,H336,H351
• Precautionary Statements: P202 - P210 - P233 - P301 + P312 - P305 + P351 + P338 - P308 + P313
• 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
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves