Tetrabutylammonium fluoride Chemical Properties

Melting point:

62-63 °C(lit.)

Density 

0.953 g/mL at 25 °C

refractive index 

n20/D 1.456

Flash point:

1 °F

storage temp. 

2-8°C

solubility 

Miscible with terahydrofuran, acetonitrile, dimethyl sulfoxide and organic solvents.

form 

Solution

color 

Clear light greenish to brown

Water Solubility 

Insoluble in water.

Sensitive 

Hygroscopic

Merck 

14,9187

BRN 

3570522

Exposure limits

ACGIH: TWA 2.5 mg/m3
NIOSH: IDLH 250 mg/m3

CAS DataBase Reference

429-41-4(CAS DataBase Reference)

EPA Substance Registry System

1-Butanaminium, N,N,N-tributyl-, fluoride (429-41-4)

Safety Information

Hazard Codes 

C,F,Xi

Risk Statements 

34-19-11-36/37/38-40-37

Safety Statements 

26-27-36/37/39-45-33-29-16-36

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

F 

3

Hazard Note 

Flammable/Irritant

TSCA 

Yes

HazardClass 

3

PackingGroup 

II

HS Code 

29239000

MSDS

• Language:English Provider:TBAF
• Language:English Provider:SigmaAldrich

Tetrabutylammonium fluoride Usage And Synthesis

Chemical Properties

Clear light greenish to amber or brown solution

Uses

Catalyst for etherification of alcohols and phenols with alkyl halides Catalyst for benzylation reactions.

Uses

Tetrabutylammonium fluoride is a reagent in organic syntheses in addition, condensation, base-catalyzed cyclization reactions, fluorination and desulfonylation reactions and as a deprotecting agent. Typically dried prior to use.

Uses

Tetrabutylammonium fluoride (TBAF) is a commonly used organic soluble fluoride salt. It is used as a base, a phase transfer catalyst, and as a fluoride source. In the research field of fluoride sensor development, TBAF is used as an easy to handle and measurable fluoride anion source. The fluoride in TBAF, once dissolved, can be thought of as a free fluoride with little interaction with the ammonium cation. Since TBAF should not absorb light at wavelengths greater than 240nm, it is useful to monitor sensing reactions with visible spectroscopy.

Definition

ChEBI: Tetrabutylammonium fluoride is a fluoride salt and a tetrabutylammonium salt. It has a role as a phase-transfer catalyst.

Synthesis

Synthesis of TBAF; Anhydrous tetrabutylammonium fluoride (TBAF):; 0.67 g of tetrabutylammonium cyanide (TBACN) was dissolved in 2.5 ml of tetrahydrofuran (THF) and the resulting solution was cooled to -65 °C. In a separate vessel, 0.3 mL of hexafluorobenzene (C6F6) was dissolved in 0.5 mL of THF and cooled to -65°C. The hexafluorobenzene solution was slowly added to the cooled TBACN solution and the mixture was gradually warmed (over 4 hours) to -15°C. During the reaction, the solution changed from colorless to yellow-green and precipitated a white solid. The mixture was cooled again to -65 °C, the solid was collected by filtration and washed twice with cold THF. All separation operations need to be carried out below -36°C. The resulting white or light yellow TBAF solid can be stored in a refrigerator at -36°C for a short period of time. If the reaction mixture is used directly, the overall yield of TBAF exceeds 95% (based on TBACN, as verified by burst experiments with benzyl chloride). Isolated yields of the solid product ranged from 40% to 70%, depending on the efficiency of the washing and filtration steps.1H NMR ((CD3)2SO) δ 3.23 (8H, m), 1.56 (8H, m), 1.28 (8H, sextuple peak, J = 7.31 Hz), 0.86 (12H, t, J = 7.31 Hz); 19F NMR ((CD3)2SO) δ -72.6 ppm(s); 13C NMR ((CD3)2SO) δ 57.5, 23.1, 19.2, 13.5 ppm.

References

[1] Patent: US2006/89514, 2006, A1. Location in patent: Page/Page column 5
[2] Patent: US2006/89514, 2006, A1. Location in patent: Page/Page column 5
[3] Patent: US2006/89514, 2006, A1. Location in patent: Page/Page column 5
[4] Patent: US2006/89514, 2006, A1. Location in patent: Page/Page column 5
[5] Patent: US2006/89514, 2006, A1. Location in patent: Page/Page column 5

Tetrabutylammonium fluoride(429-41-4)Related Product Information

• TETRABUTYL AMMONIUM BROMIDE
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• Tetrabutylammonium iodide
• FLUORIDE STANDARD
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• Ammonium fluoride
• Tetrabutylammonium perchlorate
• Tetrabutylammonium hydroxide
• Tetrabutylammonium bromide
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• TETRABUTYLAMMONIUM FLUORIDE
• TETRABUTYLAMMONIUM FLUORIDE HYDRATE,TETRABUTYLAMMONIUM FLUORIDE TRIHYDRATE,Tetrabutylammonium fluoride trihydrate 97%
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• Tetrabutylammonium hexafluorophosphate
• Tetrabutylammonium tribromide
• Tetrabutylammonium nitrate
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