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:

bis(η5-pentamethylcyclopentadienyl)cobalt(III) hexafluorophosphate

1-methyl-1H-imidazole

1-Butylimidazole

1-butyl-3-methylimidazolium chloride

Refernces

Sintered silicon carbide: A new ceramic vessel material for microwave chemistry in single-mode reactors

10.1002/chem.201001703

The research explores the use of sintered silicon carbide (SiC) as a novel ceramic material for reaction vessels in microwave chemistry. The purpose of this study is to leverage SiC's high microwave absorptivity, thermal conductivity, and chemical inertness, which allows for efficient heating and improved control over reaction conditions, particularly in extreme temperature and pressure regimes. The conclusions drawn from the research indicate that SiC vessels provide almost complete shielding from electromagnetic fields, effectively separating thermal from specific/nonthermal microwave effects on chemical reactions. This technology enables the safe use of corrosive reagents at high temperatures and pressures, which is not feasible with standard glass vessels. The chemicals used in the process include a variety of solvents with different microwave absorbtivities, such as hexane, acetonitrile (MeCN), ethanol (EtOH), and 1-butyl-3-methylimidazolium hexafluorophosphate (bmimPF6), as well as reagents like triethylamine trihydrofluoride (TREAT-HF) and strong aqueous bases like potassium hydroxide (KOH) for various reaction scenarios.

Promoting effect of ionic liquids on ligand substitution reactions

10.1016/j.jorganchem.2005.02.018

The research investigates how ionic liquid solvents influence ligand substitution reactions, specifically focusing on the displacement of anionic ligands by pyridine derivatives in trans-(Ph3P)2Rh(CO)NO3. The study aims to understand the effects of ionic liquids on reaction rates, mechanisms, and selectivity, particularly in the context of homogeneous catalytic processes. 1-butyl-3-methylimidazolium hexafluorophosphate ([C4mim][PF6]) plays a crucial role as a solvent medium for studying ligand substitution reactions. Specifically, it is used to investigate how ionic liquids can influence the displacement of anionic ligands by neutral molecules in the complex trans-(Ph3P)2Rh(CO)NO3. Key chemicals used include various pyridine derivatives such as 2-fluoropyridine and 2,6-difluoropyridine. The researchers found that these ionic liquids significantly promote the formation of charge-separated ligand substitution products compared to dichloromethane, with [C4mim][PF6] showing a stronger effect than [C6pyr][Tf2N]. The study concludes that ionic liquids can enhance catalytic processes where anionic ligands compete for coordination to the active site, and their weak coordinating ability makes them suitable alternatives to traditional polar organic solvents in such reactions.

Sodium borohydride reduction of aldehydes and ketones in the recyclable ionic liquid [bmim]PF₆

10.1081/SCC-100105664

J. Howarth, P. James, and R. Ryan investigates the use of the ionic liquid [BMIM]PF6 as a solvent for the reduction of aldehydes and ketones with sodium borohydride (NaBH4). The study demonstrates that this reduction can be effectively carried out in [BMIM]PF6, and the ionic liquid can be recycled for reuse. In some cases, the product alcohols can be directly distilled from the ionic liquid, eliminating the need for classical organic solvents. The researchers tested the reduction of six common aldehydes and ketones, achieving good yields and purity of the resulting alcohols. This work highlights the potential of [BMIM]PF6 as an environmentally friendly alternative to traditional solvents in organic synthesis, particularly for reactions involving sodium borohydride.