Tetrabutylammonium fluoride

Base Information

• Chemical Name: Tetrabutylammonium fluoride
• CAS No.: 429-41-4
• Deprecated CAS: 73476-21-8,1208325-76-1,1884467-20-2
• Molecular Formula: C16H36FN
• Molecular Weight: 261.467
• Hs Code.: 29239000
• European Community (EC) Number: 207-057-2
• UNII: 2618F0C37I
• DSSTox Substance ID: DTXSID10883381
• Wikipedia: Tetra-n-butylammonium_fluoride
• Wikidata: Q423664
• Metabolomics Workbench ID: 58016
• ChEMBL ID: CHEMBL1078233
• Mol file: 429-41-4.mol

Synonyms:Bu(4)NBr;tetra-n-butylammonium dodecylsulfate;tetra-n-butylammonium hexafluorophosphate;tetrabutylammonium;tetrabutylammonium azide;tetrabutylammonium bromide;tetrabutylammonium chloride;tetrabutylammonium cyanide;tetrabutylammonium fluoride;tetrabutylammonium hydrogen sulfate;tetrabutylammonium hydroxide;tetrabutylammonium iodide;tetrabutylammonium monophosphate;tetrabutylammonium nitrate;tetrabutylammonium perchlorate;tetrabutylammonium sulfate;tetrabutylammonium sulfate (1:1), sodium salt

Chemical Property of Tetrabutylammonium fluoride

Chemical Property:

• Appearance/Colour: clear light greenish to amber or brown solution
• Melting Point: 62-63 °C
• Refractive Index: n20/D 1.456
• Flash Point: -17 °C
• PSA: 0.00000
• Density: 0.953 g/mL at 25 °C
• LogP: 2.00760
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: Miscible with terahydrofuran, acetonitrile, dimethyl sulfoxide a
• Water Solubility.: Insoluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 12
• Exact Mass: 261.28317831
• Heavy Atom Count: 18
• Complexity: 116

Purity/Quality:

99% ^*data from raw suppliers

Tetrabutylammonium fluoride hydrate 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, F, C
• Hazard Codes: C,F,Xi
• Statements: 34-19-11-36/37/38-40-37
• Safety Statements: 26-27-36/37/39-45-33-29-16-36

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Quaternary Amines
• Canonical SMILES: CCCC[N+](CCCC)(CCCC)CCCC.[F-]
• Uses: Catalyst for etherification of alcohols and phenols with alkyl halides Catalyst for benzylation reactions. 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. 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.

Technology Process of Tetrabutylammonium fluoride

There total 21 articles about Tetrabutylammonium fluoride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → tetrabutyl ammonium fluoride (429-41-4)

Guidance literature:

With potassium fluoride; potassium hydroxide; for 0.333333h; Ambient temperature;

DOI:10.1055/s-1988-27763

Reference yield: 95.0%

tetrabutylammonium hydrogen bifluoride (193819-24-8) → tetrabutyl ammonium fluoride (429-41-4)

Guidance literature:

With 1-(trimethylsilyloxy)cyclopentene; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1055/s-1999-2583

Reference yield: 70.0%

tetra-n-butylammonium cyanide (10442-39-4) → tetrabutyl ammonium fluoride (429-41-4)

Guidance literature:

With Hexafluorobenzene; In tetrahydrofuran; at -65 - -15 ℃; for 4h;

DOI:10.1021/ja0440497

upstream raw materials:

tetrabutylammomium bromide

tetrabutyl-ammonium chloride

tetrabutylammonium tetrafluoroborate

tetra(n-butyl)ammonium hydrogensulfate

Downstream raw materials:

(n-butylthio)benzene

1-(butylsulfinyl)benzene

1-dodecyl alcohol

1-fluorododecane

Refernces

• 1、 Landini, Dario,Molinari, Henriette,Penso, Michele,Rampoldi, Alessandro. "Convenient Procedures for the Preparation of Lipophilic Quaternary Onium Fluorides, Hydrogendifluorides and Dihydrogentrifluorides via Ion Exchange in Two-Phase Systems". . p. 953 - 955. Retrieved 1988.
• 2、 Dou, Chuandong,Guo, Jiaxiang,Wang, Yue,Yang, Yue. "Boron-Containing Organic Diradicaloids: Dynamically Modulating Singlet Diradical Character by Lewis Acid-Base Coordination". supporting information. p. 18272 - 18279. Retrieved 2021/11/12.
• 3、 Kelly, Michael J.,Broomsgrove, Alexander E.J.,Morgan, Ian R.,Siewert, Inke,Fitzpatrick, Philip,Smart, Jessica,Vidovic, Dragoslav,Aldridge, Simon. "Syntheses and anion binding capabilities of bis(diarylboryl) ferrocenes and related systems". . p. 2674 - 2684. Retrieved 2013/06/26.