1-Butyl-3-methylimidazolium hexafluorophosphate

Base Information

• Chemical Name: 1-Butyl-3-methylimidazolium hexafluorophosphate
• CAS No.: 174501-64-5
• Molecular Formula: C8H15N2^.PF6
• Molecular Weight: 284.185
• Hs Code.: 29339900
• European Community (EC) Number: 678-095-9
• UNII: ZGE3N4O8Q9
• DSSTox Substance ID: DTXSID4047911
• Wikipedia: 1-Butyl-3-methylimidazolium_hexafluorophosphate
• Wikidata: Q4545772
• ChEMBL ID: CHEMBL3184676
• Mol file: 174501-64-5.mol

Synonyms:(bmim)(PF6);1-butyl-3-methylimidazolium hexafluorophosphate

Chemical Property of 1-Butyl-3-methylimidazolium hexafluorophosphate

Chemical Property:

• Appearance/Colour: Clear pale yellow oil
• Melting Point: 6.5 °C
• Refractive Index: n20/D 1.41
• Boiling Point: >340°C
• Flash Point: >350°C
• PSA: 22.40000
• Density: 1.38 g/mL at 20 °C(lit.)
• LogP: 4.49510
• Storage Temp.: Store below +30°C.
• Solubility.: Acetone, Methanol
• Water Solubility.: Miscible with dichloromethane, chloroform, ethyl acetate. Immiscible with water, diethyl ether and hexane.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 284.08770446
• Heavy Atom Count: 17
• Complexity: 156

Purity/Quality:

98% ^*data from raw suppliers

1-Butyl-3-methylimidazolium Hexafluorophosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCN1C=C[N+](=C1)C.F[P-](F)(F)(F)(F)F
• Uses: those consisting of tetrafluoroborate, alkylsulfate, alkylsulfonate, carboxylate, or phosphate anions are hydrophilic and are completely dissolved in water. Dupont and coworkers first reported stable hydrophobic imidazolium salt, 1-butyl-3-methylimidazolium hexafluorophosphate ([C4mim][PF6]) in 1996. Since then, this salt has been used as a typical hydrophobic IL in many chemical reactions because its mixture with water forms a biphasic layer. Furthermore, this IL shows poor solubility in hexane or ether, which allows realization of an easy work-up process. However, [C4mim][PF6] was reported to be sensitive to the moisture at high temperature and produced hazardous hydrogen fluoride as it decomposed. Therefore, bis(trifluoromethanesulfonyl)amide (NTf2) salts are now recommended as the anion for preparing hydrophobic ILs. 1-Butyl-3-methylimidazolium hexafluorophosphate is an ionic liquid employed in many environmentally friendly reactions. It can also be used as a medium for reactions such as: Ring-closing metathesis of diene and enyne substrates in the presence of a novel recyclable ruthenium carbene complex.Nickel(II)acetylacetonate catalyzed oxidation of aromatic aldehydes to the corresponding acids using dioxygen as the oxidant.Lipase-catalyzed enantioselective acylation of allylic alcohols.Allylation of aldehydes using tetraallylstannane to yield homoallylic alcohols.

Technology Process of 1-Butyl-3-methylimidazolium hexafluorophosphate

There total 22 articles about 1-Butyl-3-methylimidazolium hexafluorophosphate 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%

1-n-butyl-3-methylimidazolim bromide (85100-77-2) → 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate (174501-64-5)

Guidance literature:

With potassium hexafluorophosphate; In water; at 20 ℃;

DOI:10.1016/j.tetlet.2011.08.085

Reference yield: 100.0%

1-butyl-3-methylimidazolium chloride (79917-90-1) → 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate (174501-64-5)

Guidance literature:

With Amberlyst A-26 (PF₆^- form); In methanol;

DOI:10.3390/molecules17044007

Reference yield: 100.0%

1-methyl-3-(n-butyl)imidazolium iodide (65039-05-6) → 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate (174501-64-5)

Guidance literature:

With Amberlyst A-26 (PF₆^- form); In methanol;

DOI:10.3390/molecules17044007

upstream raw materials:

1-butyl-3-methylimidazolium chloride

1-methyl-1H-imidazole

1-bromo-butane

n-Butyl chloride

Downstream raw materials:

uranium(IV) tetrafluoride

bis(1-butyl-2-diphenylphosphino-3-methylimidazolium)tetrachloridorhodium(III) hexafluorophosphate

1-butyl-3-methylimidazolium chloride

1-methyl-1H-imidazole

Refernces

• 1、 Armstrong, Daniel W.,He, Lingfeng,Liu, Yan-Song. "Examination of ionic liquids and their interaction with molecules, when used as stationary phases in gas chromatography". . p. 3873 - 3876. Retrieved 1999.
• 2、 Jan, Roohi,Rather, Ghulam Mohammad,Bhat, Mohsin Ahmad. "Association of ionic liquids in solution: Conductivity studies of [BMIM][Cl] and [BMIM][PF6] in binary mixtures of acetonitrile + methanol: Ion association in ionic liquid solutions". . p. 738 - 745. Retrieved 2013.
• 3、 Wu,Marsh, Kenneth N.,Deev, Alexander V.,Boxall, John A.. "Liquid-liquid equilibria of room-temperature ionic liquids and butan-1-ol". . p. 486 - 491. Retrieved 2003.
• 4、 Bini, Riccardo,Chiappe, Cinzia,Mestre, Veronica Llopsis,Pomelli, Christian Silvio,Welton, Thomas. "A rationalization of the solvent effect on the Diels-Alder reaction in ionic liquids using multiparameter linear solvation energy relationships". . p. 2522 - 2529. Retrieved 2008.
• 5、 Jameson, Laramie P.,Kimball, Joseph D.,Gryczynski, Zygmunt,Balaz, Milan,Dzyuba, Sergei V.. "Effect of ionic liquids on the conformation of a porphyrin-based viscometer". . p. 18300 - 18304. Retrieved 2013.
• 6、 Yanes,Gratz,Baldwin,Robison,Stalcup. "Capillary electrophoretic application of 1-Alkyl-3-methylimidazolium-based ionic liquids". . p. 3838 - 3844. Retrieved 2001.
• 7、 Endo, Takatsugu,Nishikawa, Keiko. "Thermal phase behavior of 1-butyl-3-methylimidazolium hexafluorophosphate: Simultaneous measurements of the melting of two polymorphic crystals by Raman spectroscopy and calorimetry". . p. 79 - 82. Retrieved 2013.
• 8、 Vendilo, Andrey G.,Djigailo, Dmitry I.,Smirnova, Svetlana V.,Torocheshnikova, Irina I.,Popov, Konstantin I.,Krasovsky, Vladimir G.,Pletnev, Igor V.. "18-crown-6 and dibenzo-18-crown-6 assisted extraction of cesium from water into room temperature ionic liquids and its correlation with stability constants for cesium complexes". . p. 5001 - 5016. Retrieved 2009.
• 9、 Gilbert, Alyssa,Haines, Ronald S.,Harper, Jason B.. "Understanding the effects of ionic liquids on a unimolecular substitution process: Correlating solvent parameters with reaction outcome". . p. 675 - 682. Retrieved 2019.
• 10、 Shuang Men,Yujuan Jin. "X-ray Photoelectron Spectroscopy of Imidazolium-Based Zwitterions: The Intramolecular Charge-Transfer Effect". . p. 2337 - 2340. Retrieved 2018.