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Published TCIMAIL newest issue No.196

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CAS RN: 429-41-4 | Product Number: T1338

Tetrabutylammonium Fluoride (ca. 1mol/L in Tetrahydrofuran)

Purity:

Synonyms:

TBAF (ca. 1mol/L in Tetrahydrofuran)

Product Documents:

Size	Unit Price	Belgium	Japan*
25ML	£24.00	9	≥100
100ML	£49.00	≥40	≥100
500ML	£149.00	8	≥100

*Stock available in Belgium will be delivered in 1 to 3 days
*Stock available in Japan will be delivered in 1 to 2 weeks (excludes regulated items and dry ice shipments).

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General Information plus

Product Number	T1338
Molecular Formula / Molecular Weight	C__1__6H__3__6FN = 261.47
Physical State (20 deg.C)	Liquid
Storage Temperature	Refrigerated (0-10°C)
Store Under Inert Gas	Store under inert gas
Condition to Avoid	Air Sensitive
CAS RN	429-41-4
Reaxys Registry Number	3570522
PubChem Substance ID	87577107
Merck Index (14)	9187
MDL Number	MFCD00011747

Specifications & Properties plus

Specifications

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 %

Properties (reference)

Flash point	-17 °C
Specific Gravity (20/20)	0.92
Solubility in water	Completely miscible

Safety & Regulations plus

GHS

Pictogram
Signal Word	Danger
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 mist or vapours. 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/ hearing 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.

Related Laws:

EC Number

207-057-2

Transport Information:

UN Number	UN2924
Class	3 / 8
Packing Group	II
HS Number	2923900090

Applications plus

Application

TCI Practical Example: Selective TBDPS-Deprotection of a Compound Protected by Acetonide and TBDPS Groups

Used Chemicals

5-O-tert-Butyldiphenylsilyl-2,3-O-isopropylidene-D-ribono-1,4-lactone
TBAF (ca. 1mol/L in Tetrahydrofuran) [T1338]
THF

Procedure: 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.

Experimenter’s Comments: The reaction mixture was monitored by TLC (dichloromethane:ethyl acetate = 9:1, Rf = 0.5, stained by KMnO₄ solution containing K₂CO₃ and NaOH).

Analytical Data: 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).

Other Reference

Novel Deprotection of SEM Ethers: A Very Mild and Selective Method Using Magnesium Bromide

A. Vakalopoulos, H. M. R. Hoffmann, Org. Lett. 2000, 2, 1447.

Application

Generation of Benzyne and Reaction with Furan

T1338

Reference

A New and Efficient Hypervalent Iodine-Benzyne Precursor, (Phenyl)[o-(trimethylsilyl)phenyl]iodonium Triflate: Generation, Trapping Reaction, and Nature of Benzyne
- T. Kitamura, M. Yamane, K. Inoue, M. Todaka, N. Fukatsu, Z. Meng, Y. Fujiwara, J. Am. Chem. Soc. 1999, 121, 11674.

Application

Synthesis of β,β-Difluorohomoallylic Alcohols

Typical Procedure:
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.