| Identification | More | [Name]
Tetrabutylammonium fluoride | [CAS]
429-41-4 | [Synonyms]
TBAF
TETRABUTYLAMMONIUM FLUORIDE HYDRATE
1-Butanaminium,N,N,N-tributyl-,fluoride
n,n,n-tributyl-1-butanaminiufluoride
TBAF solution
Tetrabutylammonium fluoride solution
TetranbutylammoniumfluorideMsolninTHF
Tetrabutylammonium fluoride 1.0M solution in THF
TETRABUTYLAMMONIUM FLUORIDE SOLUTION, ~7 5% IN WATER
TETRABUTYLAMMONIUM FLUORIDE, ON SILICA G EL
TETRABUTYLAMMONIUM FLUORIDE, 75 WT. % SO LUTION IN WATER
TETRABUTYLAMMONIUM FLUORIDE SOL.,~1 M IN TETRAHYDROFURAN
TETRABUTYLAMMONIUM FLUORIDE, 1.0M SOLUTI ON IN THF CONTAINING CA. 5 WT. % WATE
TetrabutylammoniumFluoride1MInThf
Tetra-n-butylammonium fluoride, 1M soln. in THF
Tetra-n-butylammonium fluoride on silica gel, ca. 1mmole/g
Tetra-n-butylammoniumfluoride,1MsolutioninTHF
Tetrabutylammonium fluoride, 1M solution in THF, containing ca. 5% water
TETRABUTYAMMONIUMFLUORIDE
Tetrabutylammonium Fluoride (TBAF) | [EINECS(EC#)]
207-057-2 | [Molecular Formula]
C16H36FN | [MDL Number]
MFCD00149980 | [Molecular Weight]
261.46 | [MOL File]
429-41-4.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear light greenish to amber or brown solution | [Melting point ]
62-63 °C(lit.)
| [density ]
0.953 g/mL at 25 °C
| [refractive index ]
n20/D 1.456
| [Fp ]
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 ]
9187 | [BRN ]
3570522 | [Exposure limits]
ACGIH: TWA 2.5 mg/m3
NIOSH: IDLH 250 mg/m3 | [InChI]
1S/C16H36N.FH/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1 | [InChIKey]
FPGGTKZVZWFYPV-UHFFFAOYSA-M | [SMILES]
[F-].CCCC[N+](CCCC)(CCCC)CCCC | [CAS DataBase Reference]
429-41-4(CAS DataBase Reference) | [Storage Precautions]
Heat sensitive | [EPA Substance Registry System]
429-41-4(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
C,F,Xi | [Risk Statements ]
R34:Causes burns.
R19:May form explosive peroxides.
R11:Highly Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S27:Take off immediately all contaminated clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S33:Take precautionary measures against static discharges .
S29:Do not empty into drains .
S16:Keep away from sources of ignition-No smoking .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 3261 8/PG 2
| [WGK Germany ]
3
| [F ]
3 | [Hazard Note ]
Flammable/Irritant | [TSCA ]
Yes | [HazardClass ]
3 | [PackingGroup ]
II | [HS Code ]
29239000 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Acute Tox. 4 Oral
Aquatic Chronic 3
Eye Irrit. 2
Repr. 2
Skin Irrit. 2 |
| Hazard Information | Back Directory | [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.
| [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 |
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