Home Cart 0 Sign in  

[ CAS No. 93457-69-3 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 93457-69-3
Chemical Structure| 93457-69-3
Structure of 93457-69-3 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 93457-69-3 ]

Related Doc. of [ 93457-69-3 ]

Alternatived Products of [ 93457-69-3 ]

Product Details of [ 93457-69-3 ]

CAS No. :93457-69-3 MDL No. :MFCD07784439
Formula : C9H20BrN Boiling Point : -
Linear Structure Formula :- InChI Key :LCZRPQGSMFXSTC-UHFFFAOYSA-M
M.W : 222.17 Pubchem ID :11009532
Synonyms :

Calculated chemistry of [ 93457-69-3 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 60.06
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : -1.05
Log Po/w (XLOGP3) : 2.99
Log Po/w (WLOGP) : -1.35
Log Po/w (MLOGP) : -1.09
Log Po/w (SILICOS-IT) : 2.05
Consensus Log Po/w : 0.31

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.9
Solubility : 0.278 mg/ml ; 0.00125 mol/l
Class : Soluble
Log S (Ali) : -2.65
Solubility : 0.493 mg/ml ; 0.00222 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.01
Solubility : 0.218 mg/ml ; 0.000982 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.18

Safety of [ 93457-69-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H302-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 93457-69-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 93457-69-3 ]

[ 93457-69-3 ] Synthesis Path-Downstream   1~52

  • 1
  • [ 120-94-5 ]
  • [ 109-65-9 ]
  • [ 93457-69-3 ]
YieldReaction ConditionsOperation in experiment
99% for 48h; Inert atmosphere;
98% at 75 - 85℃; for 2.71667h; 2; 1 Example 1 Synthesis of PYR14Br [0077] In a three neck round bottom flask, equipped with a stirring bar, an addition funnel and an argon inlet, was placed N-methyl-N-butylpyrrolidinium bis(fluorosulfonyl)imide (50.5 g, 0.156 mole) at room temperature. To this mixture was added N-methylpyrrolidine (5.15 g, 0.0605 mole). 1-Bromobutane (8.29 g, 0.0605 mole) was placed in the addition funnel. The flask was heated with oil bath to reach the solution temperature to 75° C. 1-Bromobutane was added slowly dropwise over 5 minutes. The mixture was then heated to 85° C. for 2 h and 38 minutes and then cooled to room temperature and was evacuated for 30 minutes at 200 mTorr. Yield of N-methyl-N-butylpyrrolidinium bromide was 13.16 g (98%).
98% In acetonitrile Inert atmosphere; Cooling with ice; Reflux;
98% In acetonitrile Inert atmosphere; Cooling with ice; Reflux;
97.9% In water at 70℃; for 0.416667h; Sealed tube; Green chemistry; Synthesis of PYR14Br precursor The precursor, PYR14Br, was synthesized from PYR1 and 1-Br-But through the following reaction performed in deionized water. Purified PYR1 was previously dissolved in deionized water (PYR1/H2O volume ratio equal to 1/1) and loaded into the glass reactor. Then, the appropriate amount of purified 1-Br-But was added. The latter chemical is immiscible with water and, therefore, a liquid phase separation was observed. The lower phase was mostly composed by the heavier 1-Br-But (1-Br-But density = 1.276 g cm-3; PYR1 density = 0.819 g cm-3) whereas the upper one was mainly a PYR1/water mixture. The two phases (typically, clear and slightly coloured) were mixed (by magnetic stirring) at suitable temperature and time (Fig. 1). The progressive disappearance of the lower phase (and the simultaneous increase of the upper one) has given a clear indication of the ongoing formation of the PYR14Br precursor (soluble in water and, therefore, in the upper phase). The completion of the reaction (1) has been easily detected by complete disappearance of the lower phase, e.g., a transparent, aqueous solution of PYR14Br was obtained as final product.
95% at 50℃; for 24h; Inert atmosphere;
94% In acetonitrile at 20 - 70℃;
92% at 20℃; for 48h; Inert atmosphere;
90% at 20℃; for 24h;
89.4% In acetonitrile at 50℃; for 45h; 1-Butyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide([C4mpyr][NTF2])-. General procedure: 1-methylpyrrolidine (47.94 g, 563.02 mmol) and 1-bromobutane(89.32 g, 651.88 mmol) were heated in acetonitrile at 50 °C for 45 h.The solvent was evaporated and the resulting solid was washed withdiethyl ether (3 × 200 cm3) and filtered through a Büchner funnel.The product was then dried in vacuo at 50 °C for 24 h to yield 1-butyl-1-methylpyrrolidinium bromide ([C4mpyr]Br) as a white solid(111.87 g, 89.4%). Found: C, 48.15; H, 8.41; N, 6.08; S, <0.3%. Calc. forC9H20NBr: C, 48.66; H, 9.07; N, 6.30; S, <0.3%. ESI-MS: +ve mode: m/z142.15 (M+, 100%); calc. For C9H20N: 142.16. -ve mode: calc. For Br:78.91. 1H NMR (MeOD, 400 MHz): δ 1.05 (t, -CH2-CH3, 3H), 1.46 (sx,-CH2-CH3, 2H) 1.82 (p, N-CH2-CH2-, 2H), 2.26 (m, -CH2-CH2-CH2-CH2-,4H), 3.10 (s, -N-CH3, 3H), 3.40 (t, N-CH2-CH2-, 2H), 3.57 (m, -CH2-CH2-CH2-CH2-, 4H).[C4mpyr]Br (51.91 g, 233.65 mmol) was dissolved in dichloromethane(100 cm3). Lithium bis(trifluoromethylsulfonyl)amide (73.10 g,254.63 mmol) was dissolved in deionised water (100 cm3) and the solutionwasslowly added to the stirring solution of [C4mpyr]Br. Themixturewasstirred at roomtemperature for 19.5 h. The resulting two layerswere separated and the lower ionic liquid phase was washed withwater (3 × 30 cm3) before being over anhydrous sodium sulfate. Thesolvent was then removed using a rotary evaporator and the productwas then dried in vacuo at 50 °C for 24 h, to yield 1-butyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide ([C4mpyr][NTF2]) as a yellow liquid (15.89 g, 94%). Found: C, 31.37; H, 5.40; N,6.42; S, 15.17%. Calc. for C11H20F6N2O4S2: C, 31.28; H, 4.77; N, 6.63; S,15.18%. ESI-MS: +ve mode: m/z 142.15 (M+, 100%); calc. For C9H20N:142.16. -ve mode: m/z 279.91 (M-, 100%); calc. For C2F6NO4S2:279.92. 1H NMR (MeOD, 400 MHz): δ 1.03 (t, -CH2-CH3, 3H, JHH =14.72 Hz), 1.43 (sx, -CH2-CH3, 2H, JHH = 7.44 Hz), 1.80 (p, N-CH2-CH2-, 2H, JHH = 7.97 Hz), 2.23 (m, -CH2-CH2-CH2-CH2-, 4H), 3.07 (s,-N-CH3, 3H), 3.37 (t, N-CH2-CH2-, JHH = 8.48 Hz, 2H), 3.54 (m, -CH2-CH2-CH2-CH2-, 4H). 13C{1H} NMR (MeOD, 1024 MHz): δ 12.51, 19.44,21.21, 25.34, 49.00, 64.02.
85% In acetone for 24h; Heating;
81% at 20℃; for 24h; Inert atmosphere;
81% Stage #1: 1-Methylpyrrolidine; 1-bromo-butane at 20℃; for 22h; Inert atmosphere; Stage #2: In acetonitrile at 20℃; for 24h;
71% In tert-butyl methyl ether at 20℃; for 24h;
69% In toluene at 20 - 45℃; for 120h;
27% In isopropyl alcohol for 24h; Heating;
In acetone at 20℃;
In ethyl acetate
Inert atmosphere;
In acetonitrile at 20℃;
In acetonitrile at 69.99℃; for 72h; Inert atmosphere;
In ethyl acetate for 15h; Reflux; Inert atmosphere; 4.1. General synthesis for ionic liquids synthesis General procedure: A solution of the appropriate amine (275 mmol, 1.2 equiv) in ethyl acetate (120 mL) was degassed for 15 min by argon bubbling. Then, 1-alkylbromide (229 mmol, 1 equiv) was added and the resulting mixture was refluxed for 15 h under argon. Finally, the solvent was evaporated under reduced pressure (rotary evaporator). The residue was washed thoroughly with ethyl acetate (3 x 100 mL) and dried under reduced pressure to afford thefirst-generation ionic liquid as an hygroscopic white solid. The resulting product (210 mmol, 1 equiv) was added to a solution of LiNTf2 (166 mmol, 0.8 equiv) in distilled water (100 mL). The mixture was stirred at room temperature under argon for 5 h and extracted with CH2Cl2 (3 x 50 mL). The combined organic phases were then washed with water (2 x 15 mL) and brine (2 x 15 mL), and then dried over MgSO4. After filtration, the resultant mixture was stirred for 2 h with activated charcoal. A filtration on celite to remove charcoal and an evaporation under reduced pressure (rotary evaporator, 2 x 10-3 bar) afforded the colorless desired NTf2--based second-generation ionic liquid (global yield >80%).
at 40℃; Inert atmosphere;
In ethyl acetate at 20℃;
at 117℃; Glovebox; Inert atmosphere; Ionic liquid;
In ethyl acetate
at 50℃; for 168h; Inert atmosphere; Darkness;
In acetonitrile at 25℃; Electrochemical reaction;
In acetonitrile at 30 - 70℃; 2.1 General procedure for the preparation of imidazolium and pyrrolidinium halides. General procedure: To a stirred solution of 1-methylimidazole (8.91 g, 100.0 mmol) in acetonitrile (70 mL) was added requisite aliphatic halide (R2-X, 110.0 mmol) dropwise at 0 oC. The reaction mixture was stirred for 24-48 h at 30-70 oC. The mixture was concentrated under reduced pressure to afford crude 1-R2-3-methylimidazolium halide. 1-methylpyrrolidine instead of 1-methylimidazole and corresponding alkylbromide were used for the preparation of 1,1-alkylmethylpyrrolidinium bromide under neat condition. Completion of all the quaternization reaction was confirmed by 1H and 13C NMR.
In ethyl acetate Sealed tube; Cooling with ice;
In ethyl acetate at 0 - 20℃; for 26h; 2.4. Preparation of N-butyl-N-methyl pyrrolidinium (PYR14Br) PYR14Br was prepared according to an already publishedprocedure [28] using freshly distillated bromobutane and N-methylpyrrolidine in stoichiometric amounts in ethyl acetate. The reaction vessel was maintained at 0 °C for 2 hrs, left to reach roomtemperature and further stirred for 24 h. The white crystals werethenfiltrated and washed 3 times in fresh ethyl acetate. Theresidual solvent was evaporated and the PYR14Br compound wasthen dried at 80 °C for 24 h under vacuum.
In [(2)H6]acetone for 48h; Darkness;
In ethanol for 24h; Reflux;
In ethyl acetate at 20℃; for 48h; Inert atmosphere; 2.2. Synthesis of pyrrolidinium ionic liquids CnMPBr (n = 4, 6, 8 and 12) General procedure: The compound 1-methylpyrrolidine was dissolved in ethyl acetate. Then, an equimolar amount of 1-alkyl bromide CnH2n+1Br (n = 4, 6, 8and 12) in ethyl acetate was slowly added to the solution at room temperature under a nitrogen atmosphere. The reaction mixture was then stirred at room temperature for 48 h. After the reaction, the solution was filtered and the resulting residue was purified with ether absolute at least thrice. The obtained ionic liquid (IL) CnMPBr was dried under vacuum at room temperature for 24 h, and the product was obtained. The purity of the product was ascertained by 1H NMR (300 MHz, D2O).C4MPBr δ (relative to TMS): 3.36 (s, 4H), 3.25-3.13 (m, 2H), 2.89 (s,3H), 2.07 (s, 4H), 1.73-1.55 (m, 2H), 1.34-1.18 (m, 2H), 0.81 (t, 3H).
In water at 10℃; for 2h; 1 The Synthesis of N-butyl-N-methylpyrrolidinium bromide (PYR14Br) N-methylpyrrolidine (NMPD) is purified by distillation at 85°C. The purified N-methylpyrrolidine and N-butyl bromide are mixed at a molar ratio of 1:1.1, followed by adding an equal volume of deionized water with n-bromobutane, and mixing and stirring in a 10 degree Celsius ice bath. After 2 hours, the supernatant was N-butyl-N-methylpyrrolidinium bromide (PYR14Br).
In ethyl acetate at 20℃; for 48h;
0.8% at 20℃; for 20h; Inert atmosphere;

Reference: [1]Gilbert, Alyssa; Haines, Ronald S.; Harper, Jason B. [Organic and Biomolecular Chemistry, 2019, vol. 17, # 3, p. 675 - 682]
[2]Current Patent Assignee: SES AI CORP - US2014/235873, 2014, A1 Location in patent: Paragraph 0075; 0077
[3]Neale, Alex R.; Li, Peilin; Jacquemin, Johan; Goodrich, Peter; Ball, Sarah C.; Compton, Richard G.; Hardacre, Christopher [Physical Chemistry Chemical Physics, 2016, vol. 18, # 16, p. 11251 - 11262]
[4]Neale, Alex R.; Schütter, Christoph; Wilde, Patrick; Goodrich, Peter; Hardacre, Christopher; Passerini, Stefano; Balducci, Andrea; Jacquemin, Johan [Journal of Chemical and Engineering Data, 2017, vol. 62, # 1, p. 376 - 390]
[5]Montanino, Maria; Alessandrini, Fabrizio; Passerini, Stefano; Appetecchi, Giovanni Battista [Electrochimica Acta, 2013, vol. 96, p. 124 - 133]
[6]Weber, Cameron C.; Masters, Anthony F.; Maschmeyer, Thomas [Organic and Biomolecular Chemistry, 2013, vol. 11, # 15, p. 2534 - 2542]
[7]Lombardo, Marco; Chiarucci, Michel; Trombini, Claudio [Green Chemistry, 2009, vol. 11, # 4, p. 574 - 579]
[8]Hawker, Rebecca R.; Wong, Michaela J.; Haines, Ronald S.; Harper, Jason B. [Organic and Biomolecular Chemistry, 2017, vol. 15, # 30, p. 6433 - 6440]
[9]Baker, Sheila N.; Mark McCleskey; Pandey, Siddharth; Baker, Gary A. [Chemical Communications, 2004, # 8, p. 940 - 941]
[10]Bahadori, L.; Boyd, R.; Nockemann, P.; Shafeeyan, M. S.; Warrington, A. [Journal of Molecular Liquids, 2020, vol. 317]
[11]Zhou, Zhi-Bin; Matsumoto, Hajime; Tatsumi, Kuniaki [Chemistry - A European Journal, 2006, vol. 12, # 8, p. 2196 - 2212]
[12]Gilbert, Alyssa; Bucher, Götz; Haines, Ronald S.; Harper, Jason B. [Organic and Biomolecular Chemistry, 2019, vol. 17, # 42, p. 9336 - 9342]
[13]Gilbert, Alyssa; Haines, Ronald S.; Harper, Jason B. [Organic and Biomolecular Chemistry, 2020, vol. 18, # 28, p. 5442 - 5452]
[14]Strehmel, Veronika; Senkowski, Volker [Journal of Polymer Science, Part A: Polymer Chemistry, 2015, vol. 53, # 24, p. 2849 - 2859]
[15]Deng, Hui; Li, Xin; Chu, Yuan; He, Jiaqi; Cheng, Jin-Pei [Journal of Organic Chemistry, 2012, vol. 77, # 17, p. 7291 - 7298]
[16]Llewellyn Lancaster; Salter, Paul A.; Welton, Tom; Brent Young [Journal of Organic Chemistry, 2002, vol. 67, # 25, p. 8855 - 8861]
[17]Zhou, Zhi-Bin; Matsumoto, Hajime; Tatsumi, Kuniaki [Chemistry Letters, 2004, vol. 33, # 12, p. 1636 - 1637]
[18]Shirota, Hideaki; Funston, Alison M.; Wishart, James F.; Castner Jr., Edward W. [Journal of Chemical Physics, 2005, vol. 122, # 18]
[19]Location in patent: experimental part Kunze, Miriam; Montanino, Maria; Appetecchi, Giovanni B.; Jeong, Sangsik; Schoenhoff, Monika; Winter, Martin; Passerini, Stefano [Journal of Physical Chemistry A, 2010, vol. 114, # 4, p. 1776 - 1782]
[20]Location in patent: experimental part Zhu, Yan-Li; Katayama, Yasushi; Miura, Takashi [Electrochimica Acta, 2010, vol. 55, # 28, p. 9019 - 9023]
[21]Location in patent: experimental part Serizawa, Nobuyuki; Katayama, Yasushi; Miura, Takashi [Electrochimica Acta, 2010, vol. 56, # 1, p. 346 - 351]
[22]Kim, Ki-Sub; Kang, Jeong Won; Kang, Seong-Pil [Chemical Communications, 2011, vol. 47, # 22, p. 6341 - 6343]
[23]Location in patent: experimental part Chatel, Gregory; Goux-Henry, Catherine; Mirabaud, Anais; Rossi, Thomas; Kardos, Nathalie; Andrioletti, Bruno; Draye, Micheline [Journal of Catalysis, 2012, vol. 291, p. 127 - 132]
[24]Location in patent: experimental part Lau, Vincent Wing-Hei; Masters, Anthony F.; Bond, Alan M.; Maschmeyer, Thomas [Chemistry - A European Journal, 2012, vol. 18, # 26, p. 8230 - 8239]
[25]Reiter, Jakub; Jeremias, Sebastian; Paillard, Elie; Winter, Martin; Passerini, Stefano [Physical Chemistry Chemical Physics, 2013, vol. 15, # 7, p. 2565 - 2571]
[26]Verevkin, Sergey P.; Ralys, Ricardas V.; Emel'Yanenko, Vladimir N.; Zaitsau, Dzmitry H.; Schick, Christoph [Journal of Thermal Analysis and Calorimetry, 2013, vol. 112, # 1, p. 353 - 358]
[27]Jeremias, Sebastian; Carewska, Maria; Conte, Lino; Passerini, Stefano; Appetecchi, Giovanni Battista [RSC Advances, 2013, vol. 3, # 39, p. 17755 - 17761]
[28]Mutelet, Fabrice; Hassan, El-Sayed R. E.; Stephens, Timothy W.; Acree, William E.; Baker, Gary A. [Journal of Chemical and Engineering Data, 2013, vol. 58, # 8, p. 2210 - 2218]
[29]Yoshii, Kazuki; Oshino, Yosuke; Tachikawa, Naoki; Toshima, Kazunobu; Katayama, Yasushi [Electrochemistry Communications, 2015, vol. 52, p. 21 - 24]
[30]Shin, Nara; Kwon, Sohyun; Moon, Sojeong; Hong, Chae Hwan; Kim, Young Gyu [Tetrahedron, 2017, vol. 73, # 32, p. 4758 - 4765]
[31]Eshetu, Gebrekidan Gebresilassie; Jeong, Sangsik; Pandard, Pascal; Lecocq, Amandine; Marlair, Guy; Passerini, Stefano [ChemSusChem, 2017, vol. 10, # 15, p. 3146 - 3159]
[32]Hoffknecht, Jan-Philipp; Drews, Mathias; He, Xin; Paillard, Elie [Electrochimica Acta, 2017, vol. 250, p. 25 - 34]
[33]Toma, Ana M.; Raţ, Ciprian I.; Pavel, Octavian D.; Hardacre, Christopher; Rüffer, Tobias; Lang, Heinrich; Mehring, Michael; Silvestru, Anca; Pârvulescu, Vasile I. [Catalysis science and technology, 2017, vol. 7, # 22, p. 5343 - 5353]
[34]Zang, Huimin; Yao, Shun; Luo, Yingjie; Tang, Dan; Song, Hang [Chirality, 2018, vol. 30, # 11, p. 1182 - 1194]
[35]Yu, Yang; Yang, Zeyu; Ren, Shujing; Gao, Yanan; Zheng, Liqiang [Journal of Molecular Liquids, 2020, vol. 299]
[36]Current Patent Assignee: HONGDA INTERNAT BATTERY CO LTD - US10763547, 2020, B1 Location in patent: Page/Page column 7
[37]Saraswat, Juhi; Aldahmash, Badr; AlOmar, Suliman Yousef; Imtiyaz, Khalid; Rizvi, M. Moshahid Alam; Patel, Rajan [Applied Microbiology and Biotechnology, 2020, vol. 104, # 24, p. 10465 - 10479]
[38]Ameloot, Rob; Arnauts, Giel; Calderon Gonzalez, Maider; Cruz, Alexander John; Hauffman, Tom; Marcoen, Kristof; Obst, Martin [Angewandte Chemie - International Edition, 2021, vol. 60, # 49, p. 25668 - 25673][Angew. Chem., 2021, vol. 133, # 49, p. 25872 - 25877]
  • 2
  • [ 90076-65-6 ]
  • [ 93457-69-3 ]
  • [ 223437-11-4 ]
YieldReaction ConditionsOperation in experiment
In water; at 20℃; for 3h;Electrochemical reaction;Product distribution / selectivity; Butylmethylpyrrolidinium bis(trifluoromethylsulfonyl)imide was synthesized as follows: A solution of butylmethylpyrrolidinium bromide (500 g) in deionized water (1 L) was added to a solution of lithium bis(trifluoromethylsulfonyl)imide (646 g) in 1 L of deionized water. The resulting solution was stirred at room temperature for 3 hrs, after which two layers had formed. The bottom layer containing butylmethylpyrrolidinium bis(trifluoromethylsulfonyl)imide was separated, washed with deionized water (3×500 mL), and then heated at 100 C. under vacuum (0.1 mbar) for 48 hrs. Decolorizing charcoal or activated carbon (30 g) and activated alumina (100 g) were added to the molten salt. After stirring for 1 hr, the solids were removed by filtration. The purity of the molten salt was assayed by cyclic voltammetry, absorbance spectroscopy or fluorescence measurements. The treatment with charcoal or activated carbon and activated alumina may be repeated until the desired purity is obtained. EXAMPLE 6 Butylmethylpyrrolidinium bis(trifluoromethylsulfonyl)imide was prepared as follows: decolorizing charcoal or activated carbon (30 g) was added to a solution of butylmethylpyrrolidinium bromide (500 g) in deionized water (1 L). The resulting mixture was boiled for three minutes, then cooled to room temperature and filtered. The filtrate (a purified solution of butylmethylpyrrolidinium bromide) was added to a solution of lithium bis(trifluoromethylsulfonyl)imide (646 g) in 1 L of deionized water, stirred at room temperature for 3 hrs, after which two layers had formed. The bottom layer containing butylmethylpyrrolidinium bis(trifluoromethylsulfonyl)imide was separated, washed with deionized water (3×500 mL), heated at 100 C. under vacuum (0.1 mbar) for 48 hrs, and then filtered through activated alumina to give the highly pure molten salt. The purity of the molten salt was confirmed by cyclic voltammetry, absorbance spectroscopy, or fluorescence measurements. This preparative method is preferred because it provides highly pure molten salt in high yield.
In water; at 20℃; for 5h;Inert atmosphere; General procedure: A solution of the appropriate amine (275 mmol, 1.2 equiv) in ethyl acetate (120 mL) was degassed for 15 min by argon bubbling. Then, 1-alkylbromide (229 mmol, 1 equiv) was added and the resulting mixture was refluxed for 15 h under argon. Finally, the solvent was evaporated under reduced pressure (rotary evaporator). The residue was washed thoroughly with ethyl acetate (3 x 100 mL) and dried under reduced pressure to afford thefirst-generation ionic liquid as an hygroscopic white solid. The resulting product (210 mmol, 1 equiv) was added to a solution of LiNTf2 (166 mmol, 0.8 equiv) in distilled water (100 mL). The mixture was stirred at room temperature under argon for 5 h and extracted with CH2Cl2 (3 x 50 mL). The combined organic phases were then washed with water (2 x 15 mL) and brine (2 x 15 mL), and then dried over MgSO4. After filtration, the resultant mixture was stirred for 2 h with activated charcoal. A filtration on celite to remove charcoal and an evaporation under reduced pressure (rotary evaporator, 2 x 10-3 bar) afforded the colorless desired NTf2--based second-generation ionic liquid (global yield >80%).
In water; at 20℃; for 0.0333333 - 0.05h;Sealed tube; Green chemistry; PYR14TFSI was synthesized from aqueous PYR14Br and LiTFSI by the following reaction. LiTFSI was added, e.g., in slight excess with respect to the stoichiometric amount (Fig. 3), to the aqueous PYR14Br solution obtained from the purification step, resulting in the dissolution of the former immediately followed by its reaction with PYR14Br (through anion exchange which replaces Br- with TFSI-) to form hydrophobic PYR14TFSI and hydrophilic LiBr. The rapid formation of two liquid phases clearly indicated that the anion exchange reaction, driven by the intrinsic hydrophobicity of both the PYR14+ cation and the TFSI- anion, proceeded quickly. For instance, both PYR14+ and TFSI-, in which the charge is well shielded by hydrophobic groups (PYR14+) or extensively delocalized (TFSI-), do not easily form hydrogen bonds with water molecules and tend to separate from the aqueous phase forming a second (denser) liquid phase. Therefore, the disappearance itself of the (ionic liquid) PYR14TFSI product from the aqueous solution drove the exchange reaction to completion. Then, the two liquid phases were vigorously stirred at room temperature to facilitate the anion exchange reaction. After a selected time (Fig. 3) the stirring was interrupted and the phase separation took place in a few minutes. The upper phase (clear and colourless) was mostly composed of water, lithium bromide (LiBr) and LiTFSI excess whereas the lower one (uncoloured and generally slightly cloudy) was mostly constituted of PYR14TFSI ionic liquid with lithium salts (i.e., LiBr and LiTFSI) and traces of water.
In water-d2; General procedure: The dialkylpyrrolidinium bromides, BMPBr, HMPBr and DMPBr,were synthesized according to previous literature [26]. Nuclearmagnetic resonance (NMR) spectroscopy confirmed formation ofdialkylpyrrolidinium bromides. Acetone-d6 containing 0.05 vol%tetramethylsilane (TMS, Wako Pure Chemical Industries) was usedas the solvent for the ionic liquids in NMR measurements.BMPTFSA, HMPTFSA and DMPTFSA were prepared by interactingLiTFSA (Solvay) with corresponding dialkylpyrrolidinium bromidesin deionized water. Then the prepared ionic liquids wereextracted with dichloromethane (Junsei Chemical), separated byevaporation andfinally dried at 100 C for 24 hours under vacuumto eliminate residual water and dichloromethane. The watercontent in the prepared ionic liquids was lower than 10 ppm,which was confirmed using Karl Fischer method (Metrohm,831KF). Cyclic voltammetry of a Pt electrode did not show anysignificant cathodic or anodic current assignable to impurities,such as water, bromide, and oxygen in the prepared ionic liquids. Pt(acac)2 purchased from Sigma-Aldrich was used as supplied without further purification. The handling of all the chemicals wascarried out in an argon-filled glove box with a continuous gaspurification apparatus (Miwa MFG, DBO-1K-SH or DBO-1KP-KO1).
In water; at 20℃; In second step, [bmIm][NTf2] or [bmPyrr][NTf2] weresynthesized using metathesis reactions of lithium bis(trifluoromethane)sulfonimide salt(LiNTf2) with [bmIm]Br or [bmPyrr]Br in water at room temperature. Extraction of aproticionic liquids was carried out using the water-dichloromethane solvent system to give pureionic liquids.

  • 3
  • [ 93457-69-3 ]
  • N-butyl-N-methylpyrrolidinium dihydrogen phosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: N-methyl-N-butylpyrrolidinium bromide With AgOH for 2h; Stage #2: With phosphoric acid In water Further stages.;
  • 4
  • ammonium 1,1,1,5,5,5-hexafluoro-2,4-pentanedionate [ No CAS ]
  • [ 93457-69-3 ]
  • N-butyl-N-methylpyrrolidinium 1,1,1,5,5,5-hexafluoro-2,4-pentanedionate [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% In acetonitrile for 0.166667h;
  • 5
  • [ 120-94-5 ]
  • [ 109-65-9 ]
  • [ 78-93-3 ]
  • [ 93457-69-3 ]
YieldReaction ConditionsOperation in experiment
90% 9 Example 9 Example 9 A flask equipped with a thermometer, nitrogen gas inlet tube, reflux condenser, stirrer and dropping funnel was charged with 85 g (1.0 mol) of methylpyrrolidine and 400 g of 2-butanone (hereinafter referred to as MEK) and, while maintaining the temperature at 50° C. under a nitrogen stream, 205.5 g' (1.5 mol) of n-butyl bromide was added dropwise over 2 hours and, then, the temperature was maintained at 80° C. for 2 hours to drive the reaction to completion. Then, the reaction mixture was filtered to give N-methyl-N-butylpyrrolidinium bromide (hereinafter referred to as MBPyBr) as slightly yellowish white crystals. These crystals were then washed with MEK twice to give 187 g (yield 90%) of white MBPyBr.
  • 6
  • [ 33454-82-9 ]
  • [ 93457-69-3 ]
  • [ 223437-11-4 ]
  • 7
  • [ 88503-39-3 ]
  • [ 93457-69-3 ]
  • [ 1268688-15-8 ]
YieldReaction ConditionsOperation in experiment
88% In water at 20℃; for 6h; Darkness;
In not given AgBH2(CN)2 with C4H8N(Me)(Bu)Br; (1)H NMR, (13)C NMR, IR; elem. anal.;;
  • 9
  • [ 93457-69-3 ]
  • N-butyl-N-methyl pyrrolidinium tetrafluoroborate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium tetrafluoroborate In acetone for 24h;
  • 10
  • [ 63748-65-2 ]
  • [ 93457-69-3 ]
  • C4H8N(CH3)C4H9(1+)*C2B9H12(1-)=[C4H8N(CH3)C4H9]C2B9H12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% In chloroform; acetone equimol.; filtered, volatiles removed; elem. anal., TGA;
  • 11
  • [ 16484-77-8 ]
  • [ 93457-69-3 ]
  • [ 1354726-03-6 ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: (R)-Mecoprop With potassium hydroxide In water Stage #2: N-methyl-N-butylpyrrolidinium bromide In water 1.A.VIII Into a round-bottom reaction flask (100 mL) equipped with a magnetic stirrer was introduced 0.025 mol of (+)-( R)-2-(4-chloro-2- methylphenoxy)propionic acid in 30 mL of distilled water. Aqueous KOH (10%>) was added and the mixture was stirred to obtain potassium (+)-( R)-2-(4-chloro-2-methylphenoxy propionate. The aqueous solution of potassium (+)-( R)-2-(4-chloro-2-methylphenoxy propionate was added to an aqueous solution of 1 -butyl- 1-methylpyrrolidinium bromide. The reaction was carried out overnight and then the product was extracted with ethyl acetate. The organic layer was washed several times with distilled water to remove the KBr byproduct, and then the solvent was evaporated on a rotary evaporator. The product was dried in a vacuum desiccator over P2O5. Yield 99%. NMR spectra are described below. 1H NMR (DMSO-< 5) δ ppm = 0.91 (t, J= 7.3 Hz, 3H), 1.30 (sex, J= 7.4 Hz, 2H), 1.40 (d, J= 6.6 Hz, 3H), 1.65 (q, J= 4.1 Hz, 2H), 2.08 (q, J= 8.1 Hz, 4H), 2.13 (s, 3H), 2.99 (s, 3H), 3.33 (t, J= 4.3 Hz, 2H), 3.47 (t, J= 2.3 Hz, 4H), 4.27 (q, J= 6.7 Hz, 1H), 6.71 (d, J= 8.8 Hz, 1H), 7.05 (d, J = 8.7 Hz, 1H), 7.11 (s, 1H); 13C NMR δ ppm = 13.6, 16.1, 19.3, 19.4, 21.1, 25.1, 47.5, 62.9, 63.4, 75.7, 113.6, 122.6, 125.9, 128.1, 129.4, 156.0, 175.0. Elemental analysis C19H30CINO3: C = 64.12%, H = 8.50%, N = 3.94%, observed: C = 64.02%, H = 8.80%, N = 4.01%. Glass transition 255K, Mp: 264K Tonset = 516, 530, 580, 637K
  • 12
  • [ 2926-30-9 ]
  • [ 93457-69-3 ]
  • [ 367522-96-1 ]
  • 13
  • [ 262291-76-9 ]
  • [ 93457-69-3 ]
  • [ 1428431-68-8 ]
YieldReaction ConditionsOperation in experiment
98% In acetonitrile at 20℃;
  • 14
  • [ 93457-69-3 ]
  • 1-butyl-1-methylpyrrolidinium D-tartrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: silver hydroxide / water / 2 h / Darkness 2: 2 h / 20 °C / Darkness
  • 15
  • [ 93457-69-3 ]
  • 1-n-butyl-1-methylpyrrolidinium hydroxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With silver hydroxide In water monomer for 2h; Darkness;
With Amberlite IRN78 (SUPELCO) In water monomer
With strongly basic anion exchange resin In methanol
With sodium hydroxide In methanol; water monomer at 20℃; 2.2. Synthesis of Lev ILs using an ion exchange resin (3-5) General procedure: 1-Ethyl-1-methylpyrrolidinium levulinate [C2C1Pyr]Lev (3), 1-butyl-1-methylipyrrolidinium levulinate [C4C1Pyr]Lev (4), and 1-ethyl-1-methylpiperidinium levulinate [C2C1Pip]Lev (5) were synthetizedfrom bromide precursors by metathesis reaction with ionexchange resin following the procedure reported in our previouswork.[47] The Amberlite IRA400 ion exchange resin (100 g) wasactivated by suspending it in an aqueous NaOH solution (4% w/w, 500 mL) for 24 h at room temperature. The pretreated resinwas packed into a 3.5 cm diameter column and conditioned with300 mL of NaOH solution (4% w/w). The column was then washedwith water until neutrality.The selected bromide IL (18.6 mmol) was dissolved in 7:3 (v/v)CH3OH-water (100 mL) and the solution was passed through thecolumn three times. The hydroxyl-bromide substitution was followedby checking the presence of bromide in the eluted solutionusing silver nitrate solution (AgNO3 test). The test entails acidifyingthe sample with dilute nitric acid (0.1 N) and then treating it withAgNO3 in order to exclude the presence of Br anions above a concentrationof about 107 mol/L. The column was then washed with200 mL of CH3OH/water solution. A solution of levulinic acid(18.6 mmol) in 7:3 (v/v) CH3OH-water (50 mL) was added understirring to the prepared hydroxide IL solution. After 1 h at roomtemperature, the solvent was evaporated at 60 C for 12 h underreduced pressure affording, after drying in vacuo, the yellowish liquids.

  • 16
  • [ 93457-69-3 ]
  • [ 1431966-93-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: silver hydroxide / water / 2 h / Darkness 2: 2 h / 20 °C / Darkness
  • 18
  • [ 14075-53-7 ]
  • [ 93457-69-3 ]
  • N-butyl-N-methyl pyrrolidinium tetrafluoroborate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% In acetone for 16h; Inert atmosphere; Schlenk technique; Glovebox;
  • 19
  • [ 93457-69-3 ]
  • [ 1057745-51-3 ]
YieldReaction ConditionsOperation in experiment
0.88 g With bis(fluorosulfonyl)amide at 20℃; 2; 3 Example 3 Synthesis of PYR14FSI without Water [0079] From Example 1 above, 3.09 g (2.78 mmol PYR14 Br) of homogeneous liquid (mixture of 20% PYR14Br and 80% PYR14FSI) at 85° C. was placed in a 25 mL round bottomed flask with a magnetic stirrer and an argon inlet adaptor and was cooled to room temperature. Bis(fluorosulfonyl)imide (500 mg, 2.76 mmol) was added slowly without dilution in water. The resulting mixture was stirred at room temperature for 20 minutes. HBr that is produced in the reaction was removed at reduced pressure to yield 0.88 g (2.73 mmol) of additional PYR14FSI. Thus, a total 3.32 g of PYR14FSI was obtained, 2.47 g from the original solution and 0.88 g from the reaction.
With potassium bis(fluorosulfuryl)amide In water
With bis(fluorosulfonyl)imide lithium salt In water for 2h;
With bis(fluorosulfonyl)imide lithium salt In water at 20℃; Synthesis Method of N-butyl-N-methylpyrrolidinium bis(fluorosulfony)imide (PYR14FSI) The N-butyl-N-methylpyrrolidinium bromide salt synthesized in Step 1 is added to the equimolar LiFSI, followed by the addition of DI water, and the ratio of the DI water content to the bromide salt is 1:1 wt. %. After stirring at room temperature until the reaction is completed, the organic matter PYR14FSI (not water soluble) is separated from LiBr (water soluble), and PYR14FSI is washed with deionized water and separated, and the washing process is repeated three times. Finally, the product is dried in a 60 degree vacuum oven until its moisture content is of 20 ppm or less.

  • 20
  • nickel(II) chloride hexahydrate [ No CAS ]
  • ammonium tetrathiotungstate [ No CAS ]
  • [ 93457-69-3 ]
  • 1-butyl-1-methylpiperidinium nickel thiotungstate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In water; acetonitrile Synthesis Procedures 1Butyl1methylpiperidinium nickel thiotungstatecomplex [BMPip]2Ni[WS4]2 was prepared using aningenious technique described in [15]. A nickel chloride solution containing 0.238 g of NiCl2 6H2O and10 mL of a H2O-CH3CN mixture (a volume ratio of1 : 1) acidified with a few drops of acetic acid wasadded to a solution containing 0.7 g of ammoniumthiotungstate (NH4)2WS4 and 10 mL of a H2O-CH3CN mixture (a volume ratio of 1 : 3). The resultingmixture was admixed with a solution containing 2.1 gof [BMPip]Br and 15 mL of CH3CN. The formedbrown precipitate of [BMPip]2Ni(WS4)2 was filteredoff, washed with water and isopropanol, and thendried in the air. Elemental analysis: found (%): C,24.35; H, 4.3; N, 3.2; S, 27.1; Ni, 5.69; W, 35.36;calcd. (%): C, 24.13; H, 4.45; N, 2.81; S, 25.76; Ni,5.89; W, 36.93.
  • 21
  • Na(1+)*BH3CNBH2CN(1-)*2C4H8O2=NaBH3CNBH2CN*2C4H8O2 [ No CAS ]
  • [ 93457-69-3 ]
  • C2H5B2N2(1-)*C9H20N(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% In acetonitrile at 20℃; for 96h;
  • 22
  • [ 93457-69-3 ]
  • N-butyl-N-methylpyrrolidinium fluoride [ No CAS ]
YieldReaction ConditionsOperation in experiment
7.19 g With hydrogen fluoride In water at 50 - 110℃; for 3h; 37 Example 37: Synthesis of N- methyl-butyl -N- fluorinated pyrrolidine, the steps are: (1) Take a purity of 99% by mass 10g of N- pyrrolidin-butyl bromide -N- 25mL distilled water was added, was added 50mL of 40% concentration hydrofluoric acid, stirred and heated to 50oC in the original closed;(2) the raw material at least sufficient reaction 3h, then heated to 110oC, evaporate excess product hydrogen chloride gas and hydrogen fluoride gas, tail gas absorption using calcium oxide, not to get dehydrated N- butyl -N- methyl fluoride ion pyrrolidine liquid;(3) not to dehydrated -N- methyl-N- butyl-pyrrolidin-fluorinated ionic liquid was diluted with distilled water was added, the volume is not dehydrated -N- methyl-N- butyl-pyrrolidin-fluorinated ionic liquids with distilled water ratio of less than 1:50, the diluted solution was added AgNO3 solution, if precipitation production, continue to add 20mL hydrofluoric acid, repeating (1) and (2) step until no precipitate was produced, purified non-dehydrated butyl N- -N- methyl pyrrolidine fluoride ionic liquids;(4) dewatering the non-purified -N- methyl-N- butyl-pyrrolidin-fluorinated ionic liquid at 120oC under high vacuum dried for at least 48h, in addition to the depth of water, in addition to hydrogen fluoride, to give a viscous liquid, of a viscous liquid testing, viscous liquid was added to distilled water, distilled water with viscous liquid volume ratio of less than 1:50, sealed and heated to 60oC, with hydrogen detector dilution residual amount of hydrogen fluoride, if the reading is greater than> 0.1ppm, continue at 120oC under high vacuum drying in addition to hydrogen fluoride untilInspection hydrogen fluoride concentration <0.1ppm; detecting if the hydrogen fluoride concentration <0.1ppm, the resultant liquid is N- methyl-pyrazol-butyl fluoride -N-Pyrrolidine ionic liquids, weighing 7.19g.
  • 23
  • [ 93457-69-3 ]
  • sodium 2-ethylhexanoic acid [ No CAS ]
  • 1-butyl-1-methylpyrrolidin-1-ium 2-ethylhexanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% In water at 40℃; Flow reactor; 6 Example 6: Synthesis of 1,1-butylmethylpyrrolidinium 2-ethylhexanoate 0.2 g (0.0009 mol) of 1,1-butylmethylpyrrolidinium bromide was dissolved in 15 g of water and the solution was added at 150 μl / min, sodium 2-ethylhexanoate(0.0011 mol) was dissolved in 15 g of water to make a volume of 150 μl / min. I flowed it through. The solution passed through the microreactor was collected and concentrated under reduced pressure to give a pale yellow solid (93%) of 1,1-butylmethylpyrrolidinium 2-ethylhexanoate. The analysis result of the obtained ionic liquid is Sound like
  • 24
  • [ 156-54-7 ]
  • [ 93457-69-3 ]
  • 1,1'-butylmethylpyrrolidinium butanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% In water at 40℃; Flow reactor; 3 Example 3: Synthesis of 1,1-butylmethylpyrrolidinium butanoate 2.0 g (0.009 mol) of 1,1-butylmethylpyrrolidinium bromide was dissolved in 20 g of water and the solution was added with 300 μl / min of sodium butanoate 1.14 g (0.010 moles) of the polymer was dissolved in 20 g of water to prepare a microreactor controlled at 40 ° C. at a flow rate of 297 μl / min. I sent it away. The solution passed through the microreactor was collected and concentrated under reduced pressure to give 1,1-butylmethyl 1.78 g (97%) of pyrrolidinium butanoate was obtained. The analysis results of the obtained ionic liquid are as follows.
  • 25
  • [ 79060-88-1 ]
  • [ 93457-69-3 ]
  • [1-butyl-1-methylpyrrolidinium][tetrakis{3,5-bis(trifluoromethyl)phenyl}borate] [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With air In acetone at 20℃; for 4h;
  • 26
  • C6F3N4(1-)*Ag(1+) [ No CAS ]
  • [ 93457-69-3 ]
  • N-butyl-N-methyl-pyrrolidinium 4,5-dicyano-2-(trifluoromethyl)imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water 2.1. Synthesis of the ionic liquid and electrolyte preparation Pyr14TDI ionic liquid (IL) was synthesized by a two-stepsynthesis route via ion exchange in aqueous solution [36-38](Fig. 1). N-butyl-N-methyl pyrrolidinium bromide (Pyr14Br) wasprepared by N-alkylation of N-methylpyrrolidine (Sigma-Aldrich).For such reaction, butyl bromide (Sigma-Aldrich, freshly distilledprior to use) was added to N-methylpyrrolidine. The second step ofthe synthesis route was the cation exchange reaction to transformLiTDI (Solvionic) into AgTDI. This was performed dropping anaqueous solution of LiTDI into a vigorously stirred aqueous solutionof excess AgNO3 (Sigma-Aldrich, >99.0%). The obtained photosen-sitive, milky-white AgTDI wasfiltered off and washed withdeionized water. Thefinal step of the IL synthesis consisted indropping an aqueous solution of Pyr14Br into a vigorously stirredsuspension of AgTDI (Pyr14Br:AgTDI molar ratio 0.95:1). ExcessAgTDI and AgBr werefiltered off. The IL was subsequently purifiedby alumina and charcoal [39] to obtain a colorless liquid. Waterwas removed with a rotary evaporator at 50 C, followed by dryingat 60 C via oil pump (103 Pa) for 24 h and turbomolecular pump(106 Pa) for additional 24 h. Karl-Fischer titration, performedwith the automatic coulometer titrator (Mettler Toledo), indicatedwater content below 10 ppm in the dried IL sample. Inductively coupled plasma-optical emission spectrometry (ICP-OES) indicatedthe silver content to be below the detection limit (0.03 ppm).The electrolyte solution (Pyr14TDI:LiTDI) was prepared bydissolving LiTDI in Pyr14TDI in the molar ratio of 1:9. Properweight amounts of LiTDI and Pyr14TDI were determined through aXS105 Analytical Balance. The estimated error of the molarcomposition is <0.05%. The electrolyte density at room tempera-ture is 1.37 g/cc, as determined by an Ultrapyc 1200e (standarddeviation on 10 runs of 0.05 g/cc).
  • 27
  • Na(1+)*BH2(CN)CHN4(1-)=Na[BH2(CN)CHN4] [ No CAS ]
  • [ 93457-69-3 ]
  • C2H3BN5(1-)*C9H20N(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% In acetonitrile at 20℃; for 168h;
  • 28
  • [ 120-94-5 ]
  • [ 109-69-3 ]
  • [ 93457-69-3 ]
YieldReaction ConditionsOperation in experiment
73.2% In ethyl acetate at 45℃; for 72h; Inert atmosphere;
  • 29
  • potassium (2,2,2-trifluoromethylsulfonyl)-N-cyanoamide [ No CAS ]
  • [ 93457-69-3 ]
  • C9H20N(1+)*C2F3N2O2S(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% In water at 0 - 20℃; for 13h; 2.5. Preparation of N-butyl-N-methyl-pyrrolidinium (2,2,2-trifluoromethylsulfonyl)-N-cyanoamide (PYR14TFSAM) PYR14TFSAM, was prepared according to the procedure publishedby Shaplov et al. [34], modified as follows: N-butyl-N-methyl-pyrrolidium bromide (20.0 g, 90.0 mmol, 1.0 eq) was dissolved indeionized water and cooled down to 0 °C. Potassium (2,2,2-trifluoromethylsulfonyl)-N-cyanoamide (21.0 g, 99.4 mmol, 1.1 eq)was added dropwise as aqueous solution. After stirring at 0 °C for1 h, the reaction was allowed to warm up and was stirred foradditional 12 h at r.t. Thereafter, the reaction mixture was extractedwith CH2Cl2 (350 mL). The combined organic layers were washedfour times with equivolumes of deionized water, dried over Na2SO4and the solvent was removed under reduced pressure. The obtainedlight yellow liquid was redissolved in acetonitrile and stirred withactivated carbon for 18 h. The suspension wasfiltrated and thesolvent removed in vacuum. The product was obtained as colorlessliquid (25.0 g, 79.3 mmol, 88% yield).1H NMR (400 MHz, CD3CN) [ppm]: δ= 0.93 (3H, t, J = 7.36 Hz,CH2-CH2-CH2-CH3), 1.34 (2H, q, J = 7.40 Hz, CH2-CH2-CH2-CH3), 1.70(2H, m, J = 7.97 Hz, CH2-CH2-CH2-CH3), 2.13 (4H, s, CH2-ring), 2.94(3H, s, N-CH3), 3.23 (2H, t, J = 8.52 Hz, CH2-CH2-CH2-CH3), 3.40 (4H,d, J = 3.20 Hz, N-CH2-ring).13C NMR (100 MHz, CD3CN) [ppm]: δ = 13.40 (1C, s), 19.92 (1C, t,J = 1.50 Hz), 21.87 (1C, s), 25.80 (1C, s), 48.67 (1C, d, J = 3.87 Hz),64.55 (1C, t, J = 2.92 Hz), 64.80 (1C, d, J = 2.38 Hz).IC (0.7 mL/min, 65 °C): 2.9 ppm Br, 6.5 ppm Cl-
  • 30
  • [ 375-22-4 ]
  • [ 93457-69-3 ]
  • C9H20N(1+)*C4F7O2(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: heptafluorobutyric Acid With potassium hydroxide In water Stage #2: N-methyl-N-butylpyrrolidinium bromide In water for 0.5h; 7 Example 7: Synthesis/ Characterization of IL A (0185) N,N-butylmethylpyrrolidinium heptadecafluorobutanoate, BMPyrr C3F7COO Aqueous saturated solution of potassium hydroxide was added dropwise to hexafluorobutanoic acid (15 g, 72 mmol) under stirring, until the pH slightly exceeded pH 7. To the resulting aqueous solution of potassium heptadecafluorobutanoate, l-butyl-3-methylpyrrolidinium bromide was added (15.98 g, 72 mmol) and the solution was stirred for 30 min. No phase separation was observed. The water was carefully evaporated. Dichloromethane (100 ml.) was added to the dry residue and the solution was placed in the fridge for 1 h to precipitate KBr. Filtration on the glass filter (porosity 4) and evaporation of DCM yielded a transparent oil which tested negative for bromides with Ag 03. (0188) *H NMR (300 MHz, CDCI3): δ = 3.72 (m, 4H), 3.52 (m, 2H), 3.21 (s, 3H), 2.78 (m, 4H), 1.76 (m, 2H), 1.43 (m, 2H), 0.99 (t, 3H) ppm (0189) 19F NMR (565 MHz, CDCI3): δ = -84.7 (t, 3F), -121.0 (q, 2F), -130.6 (broad s, 2F) ppm (0190) IR (ATR, cm"1): 2968, 1686 (C=0), 1202 (C-O), 1110 (C-N), 528 (C-F)
  • 31
  • [ 1071-83-6 ]
  • [ 93457-69-3 ]
  • [ 1354726-33-2 ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: N-(phosphonemethyl)glycine With sodium hydroxide at 30℃; Stage #2: N-methyl-N-butylpyrrolidinium bromide In water at 20℃; for 1h; 7 Glyphosate-N-methyl-N- butylpyrrolidinium saltPreparation Add to a 50 mL round bottom flaskGlyphosate 1.69g (10mmol),Distilled water (20 mL) and 10% aqueous NaOH (15 mmol),Magnetic stirring at 30°C,After the reaction solution is clarified,Join1-methyl-1-butyl bromide pyrrolidine2.22g (10mmol),The reaction was stirred at room temperature for 1 hour.Dichloromethane (3 x 20 mL) was added for extraction.After the extraction is completed,The organic phase is washed once with saturated saline solution.Distilled and washed onceRotary evaporation,And dried in a vacuum drying box to give a yellow liquid,Yield 99%.
  • 32
  • monopotassium dimethyl boranophosphate [ No CAS ]
  • [ 93457-69-3 ]
  • C2H9BO3P(1-)*C9H20N(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% In acetonitrile at 20℃; for 48h;
  • 33
  • diethyl boranophosphate monopotassium [ No CAS ]
  • [ 93457-69-3 ]
  • C9H20N(1+)*C4H13BO3P(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% In acetonitrile at 20℃; for 48h;
  • 34
  • [ 93457-69-3 ]
  • C9H20N(1+)*C5H8NO2(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: strongly basic anion exchange resin / methanol / pH > 8 2: methanol / 8 h / 20 °C / pH > 8
  • 35
  • C5H2F6O2*H3N [ No CAS ]
  • [ 93457-69-3 ]
  • N-butyl-N-methylpyrrolidinium 1,1,1,5,5,5-hexafluoro-2,4-pentanedionate [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% In water
  • 36
  • sodium methylcarbonate(trifluoromethylsulfonyl)imide [ No CAS ]
  • [ 93457-69-3 ]
  • C3H3F3NO4S(1-)*C9H20N(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile at 20℃;
  • 37
  • sodium cyano(1H-1,2,3-triazole-1-yl)dihydroborate [ No CAS ]
  • [ 93457-69-3 ]
  • 1-propyl-1-methylpyrrolidin cyano(1H-1,2,3-triazole-1-yl)dihydroborate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile at 20℃; for 96h;
  • 38
  • [ 120-94-5 ]
  • [ 71-36-3 ]
  • [ 93457-69-3 ]
YieldReaction ConditionsOperation in experiment
96.4% With ethylene glycol; potassium bromide In water; acetonitrile at 50℃; for 2h; 2 Example 2 There are three Nafion 902 cation exchange membranes in the electrolytic cell. The cation exchange membrane divides the electrolytic cell into a cathode chamber and an anode chamber. Using PtO2 as anode and graphite as cathode, an 8 mol / L ethylene glycol aqueous solution was added to the anode compartment of the electrolytic cell as an anolyte, and 10 g of N-methyltetrahydropyrrole and 8.7 g of n-butanol were added to the anode compartment. An acetonitrile mixed aqueous solution containing KBr in an amount of 5 wt% was added to the cathode compartment of the electrolytic cell as a catholyte. Turn on the power and the electrolysis temperature is 50 .Constant current electrolysis for 2h at a current density of 3A / dm2, after the completion of the electrolysis, the catholyte was taken out and extracted with 100 ml of xylene to obtain an extract. Then use 100ml of water, 50ml of saturated aqueous sodium hydrogen carbonate solution, 100 ml of water were sequentially washed, dried over anhydrous sodium sulfate, concentrated,Get N-methyl, N-butylpyrrolidine bromide ionic liquid,The yield was 96.4% and the purity was 97.5%.
  • 39
  • manganese(II) dibromide hydrate [ No CAS ]
  • [ 93457-69-3 ]
  • (1-butyl-1-methylpyrrolidinium)<SUB>2</SUB>MnBr<SUB>4</SUB> [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogen bromide In water at 99.84℃;
  • 40
  • uranyl nirate hexahydrate [ No CAS ]
  • tetraphenylmethane tetrakis-4-phosphonic acid [ No CAS ]
  • [ 93457-69-3 ]
  • 3O2U(2+)*2C25H16O12P4(8-)*8H(1+)*2C9H20N(1+)*3H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With hydrogen fluoride at 160℃; for 72h;
  • 41
  • lead(II) bromide [ No CAS ]
  • [ 93457-69-3 ]
  • Br12Pb3(6-)*6C9H20N(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
23% In N,N-dimethyl-formamide at 20℃;
  • 43
  • [ 93457-69-3 ]
  • 1-butyl-1-methylpyrrolidinium hexafluorophosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hexafluorophosphate In water at 20℃; 2 Synthesis Method of N-butyl-N-methylpyrrolidinium hexafluorophosphate (PYR14PF6) The N-butyl-N-methylpyrrolidinium bromide synthesized in Step 1 is added to a molar amount (1M) of potassium hexafluorophosphate(KPF6), followed by an addition of deionized water. The ratio of deionized water to the bromine salt is 1:1 wt. %. The mixture is stirred at room temperature until reaction is completed. The white precipitate is filtered and placed in a container. Deionized water is added to wash the white precipitate which is then filtered. The white precipitate is cleaned three times and is then dried in a 60 degree vacuum oven until it reaches a moisture content of 20 ppm or less.
  • 44
  • sodium bis(mandelato)borate [ No CAS ]
  • [ 93457-69-3 ]
  • N-butyl-N-methylpyrrolidinium bis(mandelato)borate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water at 20℃; Synthesis Method of N-butyl-N-methylpyrrolidinium bis(mandelato)borate (PYR14BMB) The N-butyl-N-methylpyrrolidinium bromide salt synthesized in Step 1 is added to a molar amount (1M) of NaBMB, followed by addition of deionized water. The ratio of deionized water to the bromine salt is 1:1 wt. %. The mixture is stirred at room temperature until reaction is completed. Dichloromethane is added to the mixture and the amount of dichloromethane added is the same as the amount of deionized water added to the bromine salt in the mixture. The Dichloromethane is separated and washed with a small amount of deionized water. The deionized water is then removed. The washing process is repeated for three times, followed by heating. The dichloromethane is removed by evaporation to obtain PYR14BMB. The product is placed in a 60 degree vacuum oven until its moisture content is of 100 ppm or less.
  • 45
  • [ 93457-69-3 ]
  • sodium bis(oxalato)borate [ No CAS ]
  • N-methyl-N-n-butyl pyrrolidinium bis(oxalato)borate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water at 20℃; Synthesis Method of N-butyl-N-methylpyrrolidinium bis(oxalate)borate (PYR14BOB) The N-butyl-N-methylpyrrolidinium bromide salt synthesized in Step 1 is added to an equimolar of NaBOB, followed by the addition of deionized water for mixing. The ratio of deionized water to the bromide salt is 1:1 wt. %. The mixture is stirred at room temperature until reaction is completed. Dichloromethane is added to the mixture and the amount of dichloromethane added is the same as the amount of deionized water added to the bromine salt in the mixture. The Dichloromethane is separated and washed with a small amount of deionized water. The deionized water is then removed. The washing process is repeated for three times, followed by heating. The dichloromethane is removed by evaporation to obtain PYR14BOB. The product is placed in a 60 degree vacuum oven until its moisture content is of 100 ppm or less.
  • 46
  • [ 409071-16-5 ]
  • [ 93457-69-3 ]
  • N-butyl-N-methylpyrrolidinium difluoro(oxalate)borate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water at 20℃; Synthesis Method of N-butyl-N-methylpyrrolidinium difluoro(oxalate)borate (PYR14ODFB) The N-butyl-N-methylpyrrolidinium bromide salt synthesized in Example 1 is added to an equimolar of NaODFB, followed by the addition of deionized water for mixing. The ratio of the deionized water to the bromide salt is 1:1 wt. %. The mixture is stirred at room temperature until the reaction is completed. Dichloromethane is added to the mixture and the amount of dichloromethane added is the same as the amount of deionized water added to the bromine salt in the mixture. The Dichloromethane is separated and washed with a small amount of deionized water. The deionized water is then removed. The washing process is repeated for three times, followed by heating. The dichloromethane is removed by evaporation to obtain PYR14ODFB. The product is placed in a 60 degree vacuum oven until its moisture content is of 100 ppm or less.
  • 47
  • [ 93457-69-3 ]
  • C9H20N(1+)*NO2(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With potassium nitrite In N,N-dimethyl-formamide at 20℃; for 2h; 4 Example 1 General procedure: A mixture of 1-ethyl-1-methylpyrrolidinium bromide (2.00 g), potassium nitrite (0.91 g), and methanol (24 mL) was stirred at 20° C. for 2 hours. The reaction mixture was filtered under reduced pressure; and the filtrate was evaporated, thereby obtaining 1-ethyl-1-methylpyrrolidinium nitrite (1.45 g) with a yield of 90%. An internal standard substance, trifluoroethanol (0.013 g), was added to the obtained 1-ethyl-1-methylpyrrolidinium nitrite (0.1 g), and the mixture was diluted with heavy water to prepare a sample for NMR measurement. Then, 1H-NMR measurement was performed. The obtained 1-ethyl-1-methylpyrrolidinium nitrite was confirmed to have a purity of 99% or more. Table 1 illustrates the content of impurities other than the main component. The water content of the methanol used in the reaction was measured with a Karl Fischer moisture meter (Table 1).
  • 48
  • [ 7789-67-5 ]
  • [ 93457-69-3 ]
  • 1-butyl-1-methylpyrrolidinium pentabromidostannate(IV) [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% at 120℃; for 4h; Schlenk technique;
  • 49
  • lead(II) bromide [ No CAS ]
  • [ 93457-69-3 ]
  • Bmpip<SUB>2</SUB>PbBr<SUB>4</SUB> [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol at 70℃; 4 Synthesis Example 4: Synthetic Compound 4 (Bmpip2PbBr4) 0.4mmol of PbBr2 and 0.8 mmol of BmpipBr were added to 2 ml of ethanol, heated at a temperature of 70° C., and then sufficiently stirred to become a transparent or clear solution.The stirred solution at a temperature of 70°C was slowly cooled to room temperature at a cooling rate of about 5°C per hour, thereby forming a single crystal.The product was dried in a glove box in a nitrogen atmosphere, washed several times by diethyl ether, and then dried in vacuo to thereby obtain Bmpip2PbBr. 4compound.
  • 50
  • germanium(II) bromide [ No CAS ]
  • [ 93457-69-3 ]
  • Bmpip<SUB>2</SUB>GeBr<SUB>4</SUB> [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol at 20℃; 1 Synthesis example 1: Synthetic compound 1 (Bmpip2GeBr4) 0.5 mmol of GeBr2and 1.0 mmol of 1-butyl-1-methylpiperidinium (Bmpip) Br were added to 3 ml of ethanol, and then stirred at room temperature to produce a transparent or clear solution.In this case, because the powder is completely dissolved, the solution can be transparent or clear.In order to effectively form a single crystal at the interface between diethyl ether and the solution, 2 ml of diethyl ether was slowly injected into it.The solution distributed on the interface is collected, and then dried in a vacuum condition, thereby obtaining a Bmpip2GeBr4compound.
  • 51
  • tin(II) bromide [ No CAS ]
  • [ 93457-69-3 ]
  • Bmpip<SUB>2</SUB>SnBr<SUB>4</SUB> [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol at 70℃; 2 Synthesis Example 2: Synthetic Compound 2 (Bmpip2SnBr4) 0.4mmol of SnBr2and 0.8 mmol of BmpipBr were added to 2 ml of ethanol, heated at a temperature of 70° Cand then sufficiently stirred to become a transparent or clear solution.The stirred solution at a temperature of 70°C was slowly cooled to room temperature at a cooling rate of about 5°C per hour, thereby forming a single crystal.The product was dried in a glove box in a nitrogen atmosphere, washed several times by diethyl ether, and then dried in vacuo to thereby obtain Bmpip2SnBr4 compound.
  • 52
  • [ 93457-69-3 ]
  • 1-butyl-1-methylpyrrolidinium levulinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol; water monomer / 20 °C 2: methanol; water monomer / 1 h / 20 °C
Same Skeleton Products
Historical Records