CAS RN: 429-41-4 | Product Number: T1338
Tetrabutylammonium Fluoride (ca. 1mol/L in Tetrahydrofuran)
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|Molecular Formula / Molecular Weight||C__1__6H__3__6FN = 261.47|
|Physical State (20 deg.C)||Liquid|
|Store Under Inert Gas||Store under inert gas|
|Condition to Avoid||Air Sensitive|
|Reaxys Registry Number||3570522|
|PubChem Substance ID||87577107|
|Merck Index (14)||9187|
|Appearance||Colorless to Red to Green clear liquid|
|Concentration(Nonaqueous Titration)||1.0 to 1.1 mol/L|
|Water||max. 10.0 %|
|TBHF-HF(neutralization titration)||max. 5.0 %|
|Bromide||max. 1.0 %|
|Flash point||-17 °C|
|Specific Gravity (20/20)||0.92|
|Solubility in water||Completely miscible|
|Hazard Statements||H302 : Harmful if swallowed.
H314 : Causes severe skin burns and eye damage.
H371 : May cause damage to organs.
H372 : Causes damage to organs through prolonged or repeated exposure.
H351 : Suspected of causing cancer.
H335 : May cause respiratory irritation.
H225 : Highly flammable liquid and vapour.
|Precautionary Statements||P260 : Do not breathe dust/ fume/ gas/ mist/ vapours/ spray.
P210 : Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.
P370 + P378 : In case of fire: Use dry sand, dry chemical or alcohol-resistant foam to extinguish.
P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water.
P304 + P340 + P310 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Immediately call a POISON CENTER/doctor.
P305 + P351 + P338 + P310 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER/doctor.
|Class||3 / 8|
- TBAF (ca. 1mol/L in Tetrahydrofuran) [T1338]
To a mixture of 5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-D-ribono-1,4-lactone (100 mg, 0.234 mmol) in THF (100 mL) was cooled with an ice/water bath. TBAF (ca. 1 mol/L in THF, 0.3652 mL, 0.352 mmol) was added dropwise to the mixture and stirred at the same temperature for 2 h. sat. NH4Cl aq. (10 mL) and ethyl acetate (25 mL) were added to the reaction mixture and the two layers were separated. The organic layer was washed with water (10 mL), sat. NaCl aq. (10 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was triturated in hexane (5 mL) to give 2,3-O-isopropylidene-D-ribonic γ-lactone (0.0389 g, 88% yield) as a white solid.
The reaction mixture was monitored by TLC (dichloromethane:ethyl acetate = 9:1, Rf = 0.5, stained by KMnO4 solution containing K2CO3 and NaOH).
1H NMR (400 MHz, CDCl3); δ 4.82(d, 1H, J = 5.6 Hz), 4.76 (d, 1H, J = 5.6 Hz), 4.61 (t, 1H, J = 2.0 Hz), 4.00 – 3.95 (1H, m), 3.83 - 3.78 (1H, m), 1.88 (1H, t, J = 5.2 Hz), 1.47 (3H, s), 1.37 (3H, s).
- Novel Deprotection of SEM Ethers: A Very Mild and Selective Method Using Magnesium Bromide
- A New and Efficient Hypervalent Iodine-Benzyne Precursor, (Phenyl)[o-(trimethylsilyl)phenyl]iodonium Triflate: Generation, Trapping Reaction, and Nature of Benzyne
Under an argon atmosphere, TBAF (1.0 M in THF, 1.5 mL, 1.5 mmol) is added into a suspension of flame-dried MS4Å (1.0 g) in THF (4.0 mL) and the mixture is stirred at room temperature for 2.0 h. Then the mixture is cooled at －20 °C and a solution of ethyl 4,4-difluoro-3-(triethylsilyl)but-3-enoate (265 mg, 1.0 mmol) and benzaldehyde (204 µL, 2.0 mmol) is added to the mixture over 1.0 h at －20 °C. After stirring the mixture for
1 h at the same temperature, the whole is poured into aqueous 10% HCl, extracted with Et2O and the organic layer is dried with anhydrous MgSO4. After evaporation of the solvent, the residue is purified by column chromatography (SiO2, EtOAc : hexane) to give the desired product.
- New approach to synthesize β,β-difluorohomoallylic alcohols
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