Production Method 1

120-94-5

93457-69-3

Reaction Conditions

1.1 Solvents: Acetonitrile ;  5 - 10 bar, 40 - 45 °C

Reference

Synthesis, characterization and radiolytic properties of bis(oxalato)borate containing ionic liquids

Lall-Ramnarine, Sharon I.; Castano, Alejandra; Subramaniam, Gopal; Thomas, Marie F.; Wishart, James F., Radiation Physics and Chemistry, 2009, 78(12), 1120-1125

Production Method 2

120-94-5

93457-69-3

Reaction Conditions

1.1 Solvents: Acetonitrile ;  0 °C; 0 °C → rt; overnight, reflux

Reference

Physical-Chemical Characterization of Binary Mixtures of 1-Butyl-1-methylpyrrolidinium Bis{(trifluoromethyl)sulfonyl}imide and Aliphatic Nitrile Solvents as Potential Electrolytes for Electrochemical Energy Storage Applications

Neale, Alex R. ; Schutter, Christoph; Wilde, Patrick; Goodrich, Peter; Hardacre, Christopher ; et al, Journal of Chemical & Engineering Data, 2017, 62(1), 376-390

Production Method 3

120-94-5

93457-69-3

Reaction Conditions

1.1 Solvents: Acetonitrile ;  6 min, 45 °C; 2 min, 45 °C

Reference

Electron solvation dynamics and reactivity in ionic liquids observed by picosecond radiolysis techniques

Wishart, James F.; Funston, Alison M.; Szreder, Tomasz; Cook, Andrew R.; Gohdo, Masao, Faraday Discussions, 2012, 154, 353-363

Production Method 4

120-94-5

93457-69-3

Reaction Conditions

1.1 Solvents: Acetonitrile ;  rt; 12 h, rt; 3 h, 70 °C; 70 °C → rt

Reference

A recyclable triethylammonium ion-tagged diphenylphosphine palladium complex for the Suzuki-Miyaura reaction in ionic liquids

Lombardo, Marco; Chiarucci, Michel; Trombini, Claudio, Green Chemistry, 2009, 11(4), 574-579

Production Method 5

120-94-5

93457-69-3

Reaction Conditions

1.1 2 d, rt

Reference

Rationalising the effects of ionic liquids on a nucleophilic aromatic substitution reaction

Hawker, Rebecca R.; Wong, Michaela J.; Haines, Ronald S.; Harper, Jason B., Organic & Biomolecular Chemistry, 2017, 15(30), 6433-6440

Production Method 6

120-94-5

93457-69-3

Reaction Conditions

1.1 Solvents: Acetonitrile ;  0 °C; 0 °C → rt; overnight, reflux

Reference

Enhancement of whole cell dioxygenase biotransformations of haloarenes by toxic ionic liquids

Allen, C. C. R.; Boudet, C. J.; Hardacre, C.; Migaud, M. E., RSC Advances, 2014, 4(38), 19916-19924

Production Method 7

120-94-5

93457-69-3

Reaction Conditions

1.1 Solvents: Acetonitrile ;  16 h, rt → 60 °C

Reference

Femtosecond Raman-Induced Kerr Effect Study of Temperature-Dependent Intermolecular Dynamics in Pyrrolidinium-Based Ionic Liquids: Effects of Anion Species

Kakinuma, Shohei; Shirota, Hideaki, Journal of Physical Chemistry B, 2019, 123(6), 1307-1323

Production Method 8

120-94-5

93457-69-3

Reaction Conditions

1.1 48 h, rt

Reference

Spirocyclic quaternary ammonium cations for alkaline anion exchange membrane applications: an experimental and theoretical study

Gu, Liang; Dong, Huilong; Sun, Zhe; Li, Youyong; Yan, Feng, RSC Advances, 2016, 6(97), 94387-94398

Production Method 9

120-94-5

93457-69-3

Reaction Conditions

1.1 48 h, rt

Reference

Understanding the effects of ionic liquids on a unimolecular substitution process: correlating solvent parameters with reaction outcome

Gilbert, Alyssa; Haines, Ronald S.; Harper, Jason B., Organic & Biomolecular Chemistry, 2019, 17(3), 675-682

Production Method 10

120-94-5

93457-69-3

Reaction Conditions

1.1 Solvents: Pyrrolidinium, 1-butyl-1-methyl-, salt with imidodisulfuryl fluoride (1:1) ;  rt → 75 °C; 5 min, 75 °C; 158 min, 75 °C → 85 °C

Reference

Process for producing ionic liquids

, World Intellectual Property Organization, , ,

Production Method 11

120-94-5

93457-69-3

Reaction Conditions

1.1 Solvents: Acetonitrile ;  273 K; 4 h, 273 K; overnight, 273 K

Reference

Thermochemical properties of some bis(trifluoromethyl-sulfonyl)imide based room temperature ionic liquids

Jagadeeswara Rao, Ch.; Venkata Krishnan, R.; Venkatesan, K. A.; Nagarajan, K.; Srinivasan, T. G., Journal of Thermal Analysis and Calorimetry, 2009, 97(3), 937-943

Production Method 12

120-94-5

71-36-3

93457-69-3

Reaction Conditions

1.1 Reagents: Potassium bromide Solvents: Acetonitrile ,  Water ;  2 h, 50 °C

Reference

Preparation method of N,N-dialkylpyrrolidine bromide ionic liquid by electrolysis and application thereof as solvent to prepare tripyridylmethylamine compound

, China, , ,

Production Method 13

120-94-5

93457-69-3

Reaction Conditions

1.1 Solvents: Acetonitrile ;  70 °C; 10 min, 70 °C; 22 h, 70 °C

Reference

Synthesis of N,N-butyl-d9-methylpyrrolidinium bis(trifluoro-methanesulfonyl)imide

Weisshaart, Duane E.; Altena, Nicole J.; Anderson, Rachel S.; McManus, Riley P.; Letcher, Austin R.; et al, Journal of Undergraduate Chemistry Research, 2013, 12(3), 75-78

Production Method 14

120-94-5

93457-69-3

Reaction Conditions

1.1 < 40 °C; 1 d

Reference

Process for preparation and purification of ionic liquids and precursors

, United States, , ,

Production Method 15

120-94-5

93457-69-3

Reaction Conditions

1.1 < 40 °C; 1 d, < 40 °C

Reference

The large scale synthesis of pure imidazolium and pyrrolidinium ionic liquids

Burrell, Anthony K.; Del Sesto, Rico E.; Baker, Sheila N.; McCleskey, T. Mark; Baker, Gary A., Green Chemistry, 2007, 9(5), 449-454

Production Method 16

120-94-5

93457-69-3

Reaction Conditions

1.1 Solvents: Ethyl acetate ;  30 min, cooled; overnight, rt; 24 h, 60 °C

Reference

Cation structure-dependence of the induced free charge density gradient in imidazolium and pyrrolidinium ionic liquids

Wang, Yufeng; Adhikari, Laxmi; Baker, Gary A.; Blanchard, G. J., Physical Chemistry Chemical Physics, 2022, 24(32), 19314-19320

Production Method 17

120-94-5

93457-69-3

Reaction Conditions

1.1 Solvents: Acetone ;  rt; 24 h, reflux

Reference

Cyclic quaternary ammonium ionic liquids with perfluoroalkyltrifluoroborates: synthesis, characterization, and properties

Zhou, Zhi-Bin; Matsumoto, Hajime; Tatsumi, Kuniaki, Chemistry - A European Journal, 2006, 12(8), 2196-2212

Production Method 18

120-94-5

93457-69-3

Reaction Conditions

1.1 48 h, rt

Reference

Base Stable Pyrrolidinium Cations for Alkaline Anion Exchange Membrane Applications

Gu, Fenglou; Dong, Huilong; Li, Youyong; Sun, Zhe; Yan, Feng, Macromolecules (Washington, 2014, 47(19), 6740-6747

Production Method 19

120-94-5

93457-69-3

Reaction Conditions

1.1 22 h, rt
1.2 Solvents: Acetonitrile ;  24 h, rt

Reference

Controlling the reactions of 1-bromogalactose acetate in methanol using ionic liquids as co-solvents

Gilbert, Alyssa; Haines, Ronald S.; Harper, Jason B., Organic & Biomolecular Chemistry, 2020, 18(28), 5442-5452

1-Butyl-1-methylpyrrolidinium bromide Raw materials

• 1-Methylpyrrolidine
• 1-Butanol

1-Butyl-1-methylpyrrolidinium bromide Preparation Products

• 1-Butyl-1-methylpyrrolidinium bromide (93457-69-3)

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  Min Kim,Jae-Joon Lee,Tengling Ye,Panagiotis E. Keivanidis,Kilwon Cho J. Mater. Chem. C, 2020,8, 1686-1696
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• Solvents and Organic Chemicals Organic Compounds

• 67805-74-7(Pyrrolidinium,1-decyl-1-ethyl-, bromide (1:1))
• 16450-38-7(5-Azoniaspiro4.4nonane Bromide)
• 608140-09-6(Pyrrolidinium, 1-methyl-1-propyl-, bromide)
• 69227-51-6(1-Ethyl-1-methylpyrrolidinium bromide)
• 32210-28-9(Pyrrolidinium, 1-decyl-1-methyl-, bromide)
• 29638-94-6(Pyrrolidinium,1,1-diethyl-, bromide (1:1))
• 51464-74-5(Pyrrolidinium,1,1'-(1,5-pentanediyl)bis[1-methyl-, bromide (1:2))
• 833446-31-4(Pyrrolidinium, 1-heptyl-1-methyl-, bromide)
• 833446-30-3(Pyrrolidinium, 1-methyl-1-pentyl-, bromide)
• 63886-17-9(Pyrrolidinium,1,1'-(1,6-hexanediyl)bis[1-ethyl-, dibromide (9CI))