Name: 65039-08-9|3-Ethyl-1-methyl-1H-imidazol-3-ium bromide|97%
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[ 65039-08-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	In acetonitrile at 40℃; for 16h; Inert atmosphere;
100%	In acetonitrile at 40℃; for 16h; Inert atmosphere;
99%	Heating;

99.7%	In isopropanol at 80℃; for 72h;
99.7%	In isopropanol at 80℃; for 72h;
98%	In toluene at 40℃; for 24h; Schlenk technique; Inert atmosphere;	2 General procedure for the synthesis of ligands 1-9 General procedure: The ligands (except 3) were all synthesized by adaptation of the methods of Starikova et al. [20]. A typical and generic procedure is described. Spectroscopic and analyses data are presented. N-monosubstituted azole (0.1mmol) and dry toluene were placed in a two-neck flask and stirred until a homogeneous solution was formed; then alkyl halide (0.3mmol) was added drop wise with continuous stirring. After addition of the alkyl halide, the mixture was stirred while heating at 40°C for 24h. The solvent was removed and the ligand was dried under vacuum. 2.2.2 1-Methyl-3-ethylimidazolium bromide (2) White solid. Yield (4.70 g, 98%). IR (ATR cm-1): 3065, 2975, 1670, 1571, 1467, 1172, 1101, 856, 789, 649, 789, 621, 417; δH (400 MHz, CDCl3): 1.47 (3H, t, J 7.3 Hz, CH3), 3.97 (3H, s, NCH3), 4.32 (2H, q, NCH2), 7.54 (2H, s, NCH) and 10.07 ppm (1H, s, CH); δC (100 MHz, CDCl3): 15.64 (CH3), 36.63 (NCH3), 45.18 (NCH2), 122.01 (NCH), 123.71 (NCH) and 136.73 ppm.; m/z (ESI) 111.5 (M+-Br-). HRMS (ESI) calcd for C6H11BrN2, 111.09222 (M+-Br-); found, 111.09196 (M+-Br-).
98%	for 1.16667h; Reflux;
98%	for 1h; Reflux;
98%	for 1h; Reflux;
97.5%	In cyclohexane at 20 - 80℃; for 24h;
96%	at 40℃; Inert atmosphere;
95%	In toluene for 3h; Heating;
95%	In toluene cooling;
95%	In neat (no solvent) at 80℃; for 0.0333333h; Microwave irradiation;	The intermediate 1-ethyl-3-methylimidazolium bromide[EMIM]Br was prepared with equimolar bromoethane(>99%) and 1-methylimidazolium (>99%) in a closed glass reactor and the reaction was enhanced by microwave(Milestone microwave lab station, Italy). Firstly, the reactor was heated to 80°C (80 w) during a period of 30 seconds and the temperature was kept for another 90 seconds(100 w) to complete this reaction. The forming of AlCl3/[EMIM]Br was prepared by slow addition of known amounts of AlCl3 (anhydrous, grain, >99%) to the formerintermediate ([EMIM]Br) in a long beaker. The temperaturewas controlled carefully in case of decomposition of the ionic liquid
95%	In neat (no solvent) for 2h; Sonication; Reflux;
94%	In neat liquid at 40℃; for 3h; Inert atmosphere;
94%	for 2h;	4.1 (1) Synthesis of 1-ethyl-3-methylimidazole bromide [Emim]Br In a 100 mL three-necked flask, add N-methylimidazole (12.315g, 0.15mol),Ethyl bromide (19.61g, 0.18mol) was slowly added dropwise using a constant pressure dropping funnel,After the dropwise addition, the reaction was carried out for 2 hours, and then allowed to stand for 6 hours.Filtered, washed with ethyl acetate,[Emim] Br (26.94 g, 94%) was obtained as white crystals.
93%	In ethanol at 80℃; for 72h;
90%	In butanone at 50 - 80℃; for 4h;	1.1 Step 1"; Synthesis of l-ethyl-3-methylimidazolium bromide; Into a flask equipped with a thermometer, a nitrogen gas inlet tube, a reflux condenser tube, a stirrer, and a dropping funnel, methylimidazole 82 g (1.0 mol) and 2-butanone(hereinafter, described as MEK) 400 g were charged. While the mixture was maintained at 50°C under nitrogen flow, ethyl bromide163.5 g (1.5 mol) was added dropwise into the mixture over 2 hours. Then, the mixture was maintained at 80°C for 2 hours and then the reaction was completed. Then, the reaction liquid was filtered to obtain l-ethyl-3-methylimidazolium bromide (hereinafter, described as EMImBr) whichwas a slight brown-white crystal. Then, this crystal was washed with MEK two times in a glove box, the inside of which was substituted with nitrogen, to obtain white EMImBr 172g (yield of 90%) .
90%	at 20℃; for 24h;
90%	In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;
87%	In toluene at 30 - 35℃; Cooling;
86%	at 40℃; for 24h;
86%	In neat (no solvent) Inert atmosphere; Schlenk technique;	General procedure for the synthesis of compound 15b-15e General procedure: The salts 15a-15e were prepared by the reported procedures. The reactions of neat alkyl halides with 1-methyl imidazole were carried out under nitrogen atmosphere. The white solid compounds were formed in the reaction mixture. These reaction mixtures were evaporated to dryness in vacuum to give white solid salts in good yield. The solid salts were highly hygroscopic in nature. All salts 15a-15e were characterized by common spectroscopic techniques.
86.3%	at 80℃; for 24h;
85%	at 40℃; for 3h; Inert atmosphere;
85%	at 35℃; for 5h;	1 Example 1 Ionic liquid 1-ethyl-3-methylimidazolium bromidePreparation of the compound:In a 100 ml three-necked flask with a condensing reflux unit,Add 1-methylimidazole (8.2 g, 0.1 mol),Ethyl bromide (11.99 g, 0.11 mol) was stirred at 35 ° C for 5 hours.A white crystalline powder was obtained which was washed with ethyl acetate to remove ethyl bromide.Dry at 80 ° C for 3 h under vacuum. The yield was 85%.
80%	In ethyl acetate at 20℃; for 7h; Reflux;
80%	In tetrahydrofuran for 72h; Reflux;
80%	In ethyl acetate Heating;
80%	at 35℃; for 25h; Neat (no solvent); Reflux;
80%	With tetrabutylammonium bromide at 110 - 115℃; for 0.5h; Neat (no solvent);
78%	In acetonitrile at 20℃; for 2h;
77%	In cyclohexane at 20℃;
67%	for 3h; Reflux;	2.3. Synthesis of 1-ethyl-3-methylimidazolium bromide Bromoethane 10.83 g (13.80 mL, 80.00 mmol) was dropwise added into N-methyl imidazole8.21 g (100.00 mmol) over 1 h while stirring magnetically and refluxed foranother 2 h. The turbidity of the solution was removed by a separatory funnel, washingwith ethyl acetate. The white product was dried in a vacuum at 50 °C, yielding 67%. 1H NMR (CD3OD):δ 8.999 (1H), 7.675 (1H), 7.599 (1H), 4.289 (2H), 3.336 (3H),1.576 (3H).
64%	In benzene for 2h; Reflux;
57.6%	for 2h; Heating;
54%	In isopropanol for 24h; Inert atmosphere;
49.7%	In acetonitrile at 70 - 80℃; for 10h; Reflux;	Synthesis of MLDE.Br 0.82g (10 mmol) 1-methylimidazole and 1.09 g (10 mmol) bromoethane were slowly added to 50 mL acetonitrile under stirring with continuous heating at 70-80C and refluxing for 10 h. It was then filtered off and recrystallized with methanol and ether, and dried under vacuum. The yield of MLDE ¢Brreached about 49.7%. The synthesis method can be showedas the followed Scheme 2.
45%	In acetonitrile at 0 - 3℃; for 68h; Inert atmosphere;	1 Production of 1-ethyl-3-methylimidazolium bromide All operations are performed in a nitrogen atmosphere.The solvent to be used is one that has been sufficiently dehydrated with a dehydrating agent and deoxygenated by nitrogen bubbling.In addition, 1-methylimidazole is distilled and purified in advance.Into a 1 L four-necked flask equipped with a Dimroth condenser, 345.6 g (3.172 mol) of 1-bromoethane and 500 mL of acetonitrile are placed.While stirring the inside of the flask and cooling to 0 to 3 ° C., 130.2 g (1.585 mol) of 1-methylimidazole is added dropwise over 2 hours.The mixture is stirred at 0 ° C. for 67 hours and then warmed to room temperature.The reaction mixture is concentrated under reduced pressure and a small amount of toluene is added.The precipitated crystals are filtered, washed with diethyl ether and dried under reduced pressure.As a result, 137.7 g (yield 45%) of 1-ethyl-3-methylimidazolium bromide is obtained.The results of elemental analysis are shown below.
	In toluene at 30℃; for 5h;
	In cyclohexane at 80℃; for 24h;
	In chloroform
	at 20℃;
	In acetonitrile at 0℃; for 24h;
	In acetonitrile at 20℃; for 72h;
	at 20℃; for 24h;
	In 1,1,1-trichloroethane for 6h; Heating;
	In toluene at 90℃; for 2h;
97.6 g	In methanol at -0.16 - 54.84℃; for 96h;
	In ethyl acetate at 20℃; for 2h; Heating / reflux;	1 9.40 g of methylimidazole (0.115 mol) in 50 ml of ethyl acetate is introduced into a 500 ml three-necked flask equipped with a condenser. 14.25 g of ethyl bromide (0.126 mol) is added dropwise at ambient temperature. Then, the mixture is left for two hours under reflux before being extracted by three times 25 ml of ethyl acetate. The product is dried under vacuum at 70° C. for thirty minutes; this is ethylmethylimidazolium bromide. NMR 1H: (200 MHz, CD3CN): δ 9.42 (t, 1H, Ha); 7.63 (d, 1H, Hb); 7.55 (d, 1H, Hc); 3.93 (s, 3H, Hd); 4.28 (q, 2H, He); 1.50 (t, 3H, Hf) This product is added dropwise at ambient temperature to a mixture containing 50 ml of water and 31.37 g of lithium bis(trifluorosulphonyl)imide (0.109 mol). Then the mixture is stirred for two hours under reflux. The product is then extracted with three times 20 ml of dichloromethane before being evaporated under vacuum at 70° C. for 30 minutes. The overall yield is 86%. NMR 1H: (200 MHz, CD3CN): δ 8.46 (s, 1H, Ha); 7.42 (s, 1H, Hb); 7.37 (s, 1H, Hc); 3.93 (s, 3H, Hd); 4.28 (q, 2H, He); 1.50 (t, 3H, Hf)
	at 64℃; for 24h;
	at 70℃;
	In toluene at 50℃;
	In acetonitrile Inert atmosphere;
	In acetonitrile at 70℃; for 24h;
	at 112℃; Large scale reaction;
	at 70℃; for 24h;
	at 90℃; for 96h; Autoclave;
	at 0℃; for 49h; Inert atmosphere;	Procedure for the synthesis of bromide ionic liquids General procedure: 1-Methylimidazole (8.21 g, 100 mmol) or 1,2-dimethylimidazole (9.61 g, 100 mmol) was placed in a two-necked round-bottomed flask. Ethyl or butyl bromide (120 or 110 mmol) was then added dropwise during 1 h under argon in at 0 °C. The reaction mixture was stirred for 48 h in a water bath at 25 °C or 40 °C. Then the mixture was washed repeatedly with small portions of ethyl acetate and Et2O, followed by removal of any starting material left in the reaction mixture. Ethyl acetate was then removed by evaporation under reduced pressure to yield the bromide ionic liquids (90~95% yield).
	at 75 - 85℃; for 72h;
	at 20℃; for 6h;
	at 50 - 80℃;
	In methanol for 13h;
	at 50℃; for 48h;	2.2. Preparation of [emim]Ac [emim]Ac was prepared following the reported procedures [14] and [15]. [emim]Br was synthesized by refluxing the N-methylimidazole with excess bromoethane at 50 °C for 48 h. The excess bromoethane was removed by evaporation and the crude product was recrystallized twice by ethyl acetate. The resulting precipitate was brownish and was dried in vacuum for 24 h under reduced pressure. Then 0.2 mol [emim]Br and 0.1 mol Pb(Ac)2·3H2O were separately dissolved in solutions of methanol-water (4:1 v/v). Upon mixing the two solutions, a precipitate of PbBr2 was produced, which was removed by filtration after cooling at -20 °C overnight. The solvent was removed from the filtrate by rotary evaporation, and the product [emim]Ac was gotted by drying in vacuum for 2 days at 80 °C.
	In acetonitrile at 80℃; for 2h;
	at 50℃; for 48h;
	at 9.84 - 29.84℃;
	at 20℃; for 24h;
	at 40℃; for 48h; Inert atmosphere;
	In toluene at 110℃;
	at 70℃; for 6h;
	at 69.84℃; Reflux;
	With sodium iodide In propan-2-one at 20℃; for 12h; Schlenk technique;
	Heating;
	at 25℃; for 24h;	2.2. Preparation of the ionic liquids (ILs) and catalyst catalyst[Emim]Br was synthesized from the reaction of 1-methylimidazole with ethyl bromide at 25C for 24 h. Thesynthesis [Emim]Br was purified by acetonitrile and ethyl acetateto wipe off the residual ethyl chloride and 1-methylimidazole,and the purified [Emim]Br was dried in vacuum drying oven at70C for 24 h. [Bmim]Br synthesis from n-butyl bromide and1-methylimidazole, [Emor]Br synthesis from ethyl bromide andmorpholine and [EPy]Br synthesis from ethyl bromide and pyridinefollowed above process.
	In cyclohexane for 48h; Reflux;
	at 75℃; for 36h; Inert atmosphere;
	at 20℃; for 24h; Inert atmosphere;
	In diethyl ether
	In toluene at 0 - 70℃; for 32h;
	at 20℃; Inert atmosphere;
	at 60℃; for 8h; Inert atmosphere;	Preparation of [EMIM]Ac 1-Methylimidazole (41.06 g, 0.50 mol) and bromoethane (65.35 g, 0.60 mol) were added into a three-neck flask fitted with reflux condenser and stirrer for 8 h at 60 °C under an argon atmosphere. After washing with diethyl ether, the obtained yellow liquid was transferred to a crystallizing dish filled with ethanol/acetone (2/1 v/v). Transparent crystal ([EMIM]Br) was obtained after 3 days followed by drying in a vacuum oven at 60 °C for 12 h.
	In acetonitrile at 64.84℃; for 1h;
	at 100℃;
	for 0.0125h; Microwave irradiation;	3.3. 1-Alkyl-3-methylimidazolium-type ILs General procedure: The synthesis of eight 1-alkyl-3-methylimidazolium bromide ILs including 1-ethyl-3-methylimidazolium ([C2mim]Br), 1-butyl-3-methylimidazolium ([C4mim]Br), 1-hexyl-3-methylimidazolium ([C6mim]Br), 1-octyl-3-methylimidazolium ([C8mim]Br), 1-decyl-3-methylimidazolium ([C10mim]Br), 1-dodecyl-3-methylimidazolium ([C12mim]Br), 1-tetradecyl-3-methylimidazolium([C14mim]Br), and 1-hexadecyl-3-methylimidazolium ([C16mim]Br) was based on literature procedures [53]. A mixture of 1-alkylbromide (60 mmol) and 1-methylimidazole (50 mmol) was placed in above microwave-assisted reactor. Upon continuous stirring and intermittent microwave irradiation for 30 s plus several additional 15 s bursts at 240 W, the ionic liquid started to form. The whole formation of ionic liquid could be monitored visibly as it turned from clear solution to opaque and finally clear again. The product, a yellow viscous liquid, was washed with diethyl ether (3 × 10 mL) followed by hexane (3 × 10 mL), and dried under vacuum at 80 °C for 24 h to give a product yield of 90%. The purity of ILs was checked by their 1H-NMR and 13C-NMR spectra. The characterization by NMR spectroscopy showed that there were no organic impurities in the ILs. The structures of the ILs are listed in Table 2.
	at 140℃; Sealed tube;
	In propan-2-one for 48h; Reflux;
	Reflux;
	In ethyl acetate at 80℃;	Preparation of organic salts Preparation of organic salts Organic salts N-Ethyl-N-methyl imidazolium bromide, ([EMIM][Br]) and N-Methyl-N-Octyl imidazolium bromide, ([OMIM][Br]) were prepared according to a literature procedure [10]. For example, under vigorous stirring 1-bromoethane (15.24 g, 121.95 mmol) was added to 1-methylimidazole (5 g, 60.98 mmol). The reaction mixture was stirred at 80 °C until two phases were formed. The top phase, containing the unreacted starting material, was decanted and ethyl acetate was added to the vessel. The product [EMIM][Br] was washed with ethyl acetate thrice and dried under vacuum at 70 °C for 6 h 1H NMR (200 MHz, CDCl3): δ 10.05 (s, 1H), 7.54 (d, 2H), 4.21 (q, 2H), 3.95 (s, 3H), 1.43 (t, 3H). The same procedure was followed for the synthesis of [OMIM][Br].
	In toluene at 20℃; for 24h;	As a typical procedure forpreparing ILs, preparation of 1-ethyl-3-methylimidazoliumethyl ethylphosphonate (8) is described as follows: to 1-methylimidazolein toluene, an excess amount of ethyl bromide wasadded at room temperature, and the resulting mixture was stirred for 24 h. During the reaction, clear liquid was separatedfrom reaction media and the precipitate formed waswashed repeatedly with diethyl ether. The precipitate was driedin vacuo at 50 °C to give 1-ethyl-3-methylimidazolium bromide([C2mim]Br) as white solid. [C2mim]Br was dissolved inMilli Q water, and the resulting solution was passed through acolumn filled with anion-exchange resin (Amberliteμ IRN-78)to give 1-ethyl-3-methylimidazolium hydroxide ([C2mim]OH)aqueous solution.
	Stage #1: 1-methyl-1H-imidazole; bromure d'ethyle Stage #2: at 35 - 40℃; for 1h; Stage #3: for 24h; Reflux;
	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.
	at 40℃; for 3h; Inert atmosphere;
	at 20℃; for 4h;	2.2 Synthesis and characterization of ILs The ILs used in this work were prepared using a typical ion-exchange method involving two steps, namely quaternization and anion metathesis [40-43]. The general equations for the reactions involved in the synthesis of these ILs are shown in Scheme 2. The chemical structures of these ILs were determined using nuclear magnetic resonance (NMR) spectroscopy. 1H NMR spectra were recorded using a JNM-ECA-600 spectrometer (JEOL Ltd., Tokyo, Japan) with DMSO-d6 as the solvent. Thermal gravimetric analysis (TGA) was performed using a TGA-Q5000 instrument (TA Instruments) in the temperature range 30-300 °C at a heating rate of 5 °C/min in a nitrogen atmosphere. The water contents of the ILs were determined using coulometric Karl Fischer titration (C20 Coulometric KF titrator, Mettler Toledo, OH, USA). Details of the IL synthesis are given below. 1-Ethyl-3-methylimidazolium bromide (EmimBr) was prepared by mixing N-methylimidazole with bromoethane at a molar ratio of 1:1.2 in a 250 mL three-necked, round-bottomed flask. The reaction was performed under ambient conditions with magnetic stirring for 4 h. A reflux condenser was connected to the flask to avoid volatilization of the reactants. The mixture components were separated by reduced pressure distillation and the resultant white solid was washed three times with ethyl acetate to remove the remaining feedstock and other impurities thoroughly. The obtained EmimBr was dried under high vacuum (-3 to 0 Pa) at 70 °C for 24 h with P2O5 as a desiccant. 1H NMR (EmimBr, DMSO-d6): 1.31 (t, 3H), 3.86 (m, 2H), 4.18 (s, 3H), 7.78 (d, 2H), 9.73 (s, H); purity: 99%.
	at 25℃; for 24h;
	In acetonitrile at 20℃; for 24h; Inert atmosphere; Cooling with ice;

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2
[ 65039-08-9 ]
[ 143314-16-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	With tetrafluoroboric acid; 1-hexene; dihydrogen peroxide; at 25℃; for 4h;	General procedure: A mixture of the appropriate imidazolium bromide (0.2 mol) and hex-1-ene (30 mL) was stirred in a flask, and a mixture of the appropriate protonic acid (0.2 mol) and H2O2 (0.1 mol) was added dropwise at room temperature (25 C). After the appropriate time (Table 1), the liquid was placed in a separatory funnel and the oil phase was removed. The aqueous phase was washed with portions of CH2Cl2 (50mL) until it was colorless. Residual H2O in the product was removed by azeotropic distillation with cyclohexane. For [BzMim]PF6 (Table 1,entry 18), which has low water solubility, post-processing required only distillation and desiccation of the oil phase.

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1999,p. 2133 - 2139
[2]Synthesis,2017,vol. 49,p. 1065 - 1072
[3]ChemPhysChem,2012,vol. 13,p. 261 - 266
[4]Journal of Fluorine Chemistry,2003,vol. 120,p. 135 - 141
[5]Chemistry - A European Journal,2009,vol. 15,p. 1341 - 1345
[6]Journal of Chemical and Engineering Data,2008,vol. 53,p. 427 - 433
[7]Journal of Chemical and Engineering Data,2009,vol. 54,p. 472 - 479
[8]Heterocyclic Communications,2009,vol. 15,p. 97 - 104

3
[ 65039-08-9 ]
[ 90076-65-6 ]
[ 174899-82-2 ]

Yield	Reaction Conditions	Operation in experiment
87.1%	In water; at 60℃; for 2h;	2. Put 200g lithium bistrifluoromethylsulfonimide, 152g 1-ethyl-3-methylimidazole bromide salt and 400g pure water into the reactor,Warm to 60 , react for 2h,After standing for a while, 283 g of crude 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide salt was obtained. 3. Wash three times with pure water to obtain 251g of pure 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide salt.Distill it on a rotary evaporator under reduced pressure for 2h,Keep the temperature at 80 , remove most of the water,Finally, it is dried in a vacuum oven at 110 C for 12h.237 g of 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide was obtained. The purity of the product detected by liquid chromatography was 99.23%, and the yield was 87.1%;Ion chromatography detection: halogen ion 450ppm;ICP detection: Fe ion <1ppm, Pb ion <1ppm.
86%	In water; at 20℃; for 2h;Heating / reflux;	9.40 g of methylimidazole (0.115 mol) in 50 ml of ethyl acetate is introduced into a 500 ml three-necked flask equipped with a condenser. 14.25 g of ethyl bromide (0.126 mol) is added dropwise at ambient temperature. Then, the mixture is left for two hours under reflux before being extracted by three times 25 ml of ethyl acetate. The product is dried under vacuum at 70 C. for thirty minutes; this is ethylmethylimidazolium bromide. NMR 1H: (200 MHz, CD3CN): delta 9.42 (t, 1H, Ha); 7.63 (d, 1H, Hb); 7.55 (d, 1H, Hc); 3.93 (s, 3H, Hd); 4.28 (q, 2H, He); 1.50 (t, 3H, Hf) This product is added dropwise at ambient temperature to a mixture containing 50 ml of water and 31.37 g of lithium bis(trifluorosulphonyl)imide (0.109 mol). Then the mixture is stirred for two hours under reflux. The product is then extracted with three times 20 ml of dichloromethane before being evaporated under vacuum at 70 C. for 30 minutes. The overall yield is 86%. NMR 1H: (200 MHz, CD3CN): delta 8.46 (s, 1H, Ha); 7.42 (s, 1H, Hb); 7.37 (s, 1H, Hc); 3.93 (s, 3H, Hd); 4.28 (q, 2H, He); 1.50 (t, 3H, Hf)
	In water; at 70℃; for 24h;pH 6.0;	General procedure: The respective halide IL was dissolved in deionized water (pH =6) and after an equimolar amount of LiNTf2 in water had been added dropwise, the reaction mixture was stirred for 1 day at 70 C. Then CH2Cl2 was added and the aqueous phase was removed. The organic phase was washed halide-free with deionized water (AgNO3 test). The solution was filtered over a column filled with neutral Al2O3 and activated charcoal. The organic solvent was removed under reduced pressure and the reaction product finally dried under dynamic vacuum for 1-2 days at 80-90 C.

383.5 g

In water;

Step 1: Take 287.1g of lithium bis (trifluoromethanesulfonyl) imide (LiTFSI) completely dissolved in water to form an aqueous solution with a mass percentage concentration of 50%; Step 2: 191.1 g of 1-ethyl-3-methylimidazolium bromide (EMIBr) was completely dissolved in water to form an aqueous solution having a mass percentage concentration of 50% Step 3: mixing the aqueous solution products obtained in steps 1 and 2 to obtain a crude product; Step 4: The crude product is obtained in step 3, washed with water for 2 times, emulsified by heating and stirring, and heated to 60 DEG C for demulsification, and then high purity product is obtained after liquid separation; Step 5: The high-purity product obtained in Step 4 was vacuum-dried at 100 C for 8 hours to obtain 383.5 g of colorless liquid EMI · TFSI product (melting point: about -15 C), purity: 99.95%, water content: 80 ppm, .

Reference： [1]Inorganic Chemistry,2018,vol. 57,p. 2314 - 2319
[2]Organic and Biomolecular Chemistry,2008,vol. 6,p. 2522 - 2529
[3]Organic Letters,2009,vol. 11,p. 1523 - 1526
[4]Chemical Communications,2010,vol. 46,p. 1488 - 1490
[5]Molecules,2011,vol. 16,p. 5963 - 5974
[6]Angewandte Chemie - International Edition,2012,vol. 51,p. 11483 - 11486
Angew. Chem.,2012,vol. 124,p. 11650 - 11654,5
[7]Organic and Biomolecular Chemistry,2013,vol. 11,p. 2534 - 2542
[8]Patent: CN110878053,2020,A .Location in patent: Paragraph 0064; 0066
[9]Patent: US2007/7137,2007,A1 .Location in patent: Page/Page column 4
[10]Chemical Communications,2017,vol. 53,p. 11154 - 11156
[11]Chemical Communications,2008,p. 4939 - 4941
[12]Analytical Chemistry,2004,vol. 76,p. 2773 - 2779
[13]Journal of the American Chemical Society,2005,vol. 127,p. 4976 - 4983
[14]Journal of Materials Chemistry,2006,vol. 16,p. 1475 - 1482
[15]Chemical Communications,2007,p. 2732 - 2734
[16]Electrochimica Acta,2010,vol. 55,p. 7145 - 7151
[17]Journal of Chemical and Engineering Data,2012,vol. 57,p. 875 - 881
[18]Science China Chemistry,2012,vol. 55,p. 1519 - 1524
[19]Journal of Molecular Liquids,2013,vol. 177,p. 361 - 368
[20]Inorganic Chemistry,2013,vol. 52,p. 13167 - 13178
[21]Dalton Transactions,2014,vol. 43,p. 568 - 575
[22]Macromolecules,2013,vol. 46,p. 9464 - 9472
[23]Journal of Molecular Liquids,2014,vol. 192,p. 191 - 198
[24]Physical Chemistry Chemical Physics,2014,vol. 16,p. 23233 - 23243
[25]Dalton Transactions,2016,vol. 45,p. 10151 - 10154
[26]Patent: CN105985277,2016,A .Location in patent: Paragraph 0029; 0030; 0031; 0032; 0033; 0034
[27]Journal of Chemical and Engineering Data,2018,vol. 63,p. 4484 - 4496

4
[ CAS Unavailable ]
[ 65039-08-9 ]
[ 174899-65-1 ]

Yield	Reaction Conditions	Operation in experiment
	In water for 24h;
	In water for 24h;
	In acetonitrile	1-methylimidazole(30 mL) and ethyl bromide (90 mL) were fully mixed in a 250 mL round bottom flaskand heated under reflux for 8 h to obtain an oily liquid. Then, the liquid was cooled toroom temperature and a white solid was obtained. Then, the white solid was dissolvedusing acetonitrile and filtered, the ethyl acetate was added to the filtrate to obtain a whitesolid. The above operations were repeated, and the recrystallized product was dried undervacuum for 36 h to obtain 1-ethyl-3-methylimidazolium bromide (EMIMBr). Then, 19.1 g ofEMIMBr and 22.4 g of silver trifluoroacetate were weighed out and added to 200 mL ofacetonitrile. Finally, the silver bromide precipitate was filtered and the acetonitrile wasremoved by rotary evaporation. The final product [EMIM] [TFA] was obtained after vacuumdrying at 60 °C. The reaction process is shown in Figure 12. The structure spectrum of[EMIM] [TFA] is as follows. IR film, cm1: C=N (3374.54 cm1); -CH2-(2941.08 cm1);C=O (1683.35 cm1); C=C(1572.82 cm1); -CH2-(1456.16 cm1); C-F(1065.90 cm1). 1HNMR(500 MHz, DMSO-d6, , ppm): 1.364 ppm (t, 3H, -(CH2)-CH3); 3.757 ppm(s, 3H,CH3); 4.081 ppm(q, 2H, CH2); 7.285 ppm(s, 1H, -CH=); 7.362 ppm(s, 1H, -CH=); 8.582 ppm(s, 1H, -CH=). The results for the FT-IR (S1) and NMR (S2) spectra are also provided in theSupplementary Data to confirm compound identity.

Reference： [1]Rodriguez, Hector; Brennecke, Joan F. [Journal of Chemical and Engineering Data, 2006, vol. 51, # 6, p. 2145 - 2155]
[2]Location in patent: body text Ficke, Lindsay E.; Rodriguez, Hector; Brennecke, Joan F. [Journal of Chemical and Engineering Data, 2008, vol. 53, # 9, p. 2112 - 2119]
[3]Jin, Nanxi; Liu, Baoyou; Tian, Jie; Wang, Xinyu; Yang, Huilong; Zhang, Peiwen [Molecules, 2021, vol. 26, # 22]

5
[ 53585-93-6 ]
[ 65039-08-9 ]
1-ethyl-3-methylimidazolium (T-4)-bis[(αR)-α-(hydroxy-kO)cyclohexylacetato-kO]borate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 2576 - 2591

6
[ 554-95-0 ]
[ 6147-53-1 ]
[ 65039-08-9 ]
[ 174899-82-2 ]
[ 951026-20-3 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 10334 - 10335

7
[ 376-73-8 ]
[ 6147-53-1 ]
[ 65039-08-9 ]
[ 174899-82-2 ]
[1-ethyl-3-methylimidazolium]2[Co₃(H₂O)4(hexafluoroglutarate)4] [ No CAS ]

Reference： [1]Dalton Transactions,2009,p. 1131 - 1135

8
[ 377-38-8 ]
[ 6147-53-1 ]
[ 65039-08-9 ]
[ 174899-82-2 ]
[1-ethyl-3-methylimidazolium]2[Co(H₂O)2(tetrafluorosuccinate)2] [ No CAS ]

Reference： [1]Dalton Transactions,2009,p. 1131 - 1135

9
[ 65039-08-9 ]
[ 174501-65-6 ]

Reference： [1]Journal of Chemical and Engineering Data,2009,vol. 54,p. 472 - 479

10
cadmium(II) nitrate tetrhydrate [ No CAS ]
[ 605-70-9 ]
[ 65039-08-9 ]
[ 143314-16-3 ]
[ 1309655-20-6 ]

Reference： [1]Inorganic Chemistry Communications,2011,vol. 14,p. 1001 - 1003

11
[ 36603-80-2 ]
[ 65039-08-9 ]
[ 666823-18-3 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: sodium tricyanomethanide With silver nitrate In water Stage #2: 3-ethyl-1-methyl-1H-imidazol-3-ium bromide In water

Reference： [1]Location in patent: experimental part Emel'Yanenko, Vladimir N.; Zaitsau, Dzmitry H.; Verevkin, Sergey P.; Heintz, Andreas; Voss, Karsten; Schulz, Axel [Journal of Physical Chemistry B, 2011, vol. 115, # 40, p. 11712 - 11717]

12
[ 6080-56-4 ]
[ 65039-08-9 ]
[ 143314-17-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	In water; at 35℃; for 48h;Inert atmosphere;	1-Ethyl-3-methylimidazolium bromine (0.2 mol) and lead (II) acetate trihydrate (0.1 mol) were dissolved in 30 mL of distilled water and 70 mL of distilled water, respectively. After they were completely dissolved, 1-ethyl-3-methylimidazolium bromine solution was poured into lead (II) acetate trihydrate solution under vigorous mechanical stirring. The reaction was carried out at 35 C for 48 h under nitrogen atmosphere. Then the reaction system was refrigerated at 3 C for 12 h and the precipitates were filtered off. The filtrates were distilled under reduced pressure to remove the water. The obtained EMIMAc (moisture content 0.02%; bromide content 0.004%) was light yellow viscous liquid and the yield was 93%.
	In methanol; water;	[emim]Ac was prepared following the reported procedures [14] and [15]. [emim]Br was synthesized by refluxing the N-methylimidazole with excess bromoethane at 50 C for 48 h. The excess bromoethane was removed by evaporation and the crude product was recrystallized twice by ethyl acetate. The resulting precipitate was brownish and was dried in vacuum for 24 h under reduced pressure. Then 0.2 mol [emim]Br and 0.1 mol Pb(Ac)2·3H2O were separately dissolved in solutions of methanol-water (4:1 v/v). Upon mixing the two solutions, a precipitate of PbBr2 was produced, which was removed by filtration after cooling at -20 C overnight. The solvent was removed from the filtrate by rotary evaporation, and the product [emim]Ac was gotted by drying in vacuum for 2 days at 80 C. The structure of [emim]Ac was confirmed by 1H NMR (400 MHz, D2O): deltaH = 1.46-1.52 (t, 3H; CH3), deltaH = 1.89-1.94 (t, 3H; CH3-COO-), deltaH = 3.89 (t, 3H; N-CH3), deltaH = 4.18-4.26 (t, 2H; CH2), deltaH = 7.4 (s, 1H; Ring-CH), deltaH = 7.5 (s, 1H; Ring-CH), deltaH = 8.7 (s, 1H; Ring-CH).

Reference： [1]Carbohydrate Polymers,2013,vol. 94,p. 505 - 510
[2]Journal of Molecular Structure,2012,vol. 1015,p. 147 - 155
[3]Carbohydrate Polymers,2012,vol. 89,p. 7 - 16

13
[ 65039-08-9 ]
[ 331717-63-6 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium thiocyanate In acetonitrile for 8h;

Reference： [1]Yu, Ying Hao; Jiang, Peng; Wang, Fu Rong; Wang, Le Fu; Li, Xue Hui [Science China Chemistry, 2012, vol. 55, # 8, p. 1608 - 1613]

14
[ 143314-17-4 ]
[ 74-95-3 ]
[ 628-51-3 ]
[ 65039-08-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	at 20℃; for 2h;Inert atmosphere;	Examples 3 and 4: methylene diacetate A 50 mL Schlenk flask was equipped with a magnetic stirring bar, EMIM-acetate (20.0 g, 117.0 mmol), and 0.5 equivalents of dichloromethane (5.0 g, 58.7 mmol) were added at room temperature and the reaction was stirred at 50C for 16h. After reaction the pure Product was distilled from the reaction mixture at 80C under reduced pressure (85.0-%). When dibromomethane was used as substrate the reaction was fast even at room temperature and highly exothermic. The reaction proceeds via homogeneous path way and the pure product distilled from the reaction mixture at 80C under reduced pressure (86.0% yield). Methylene diacetate: 1H NMR (CD3CN, 400.13 MHz): delta = 2.04 (s, 6H, CH3), 5.64 (s, 2H, CH2); 13C NMR: delta = 20.9 (CH3), 79.7 (CH2), 170.8 (CO); FTIR (ATR mode): v = 2996 (br), 1758 (s), 1190 (s), 1009 (s), 978 (s)

Reference： [1]Patent: EP2532646,2012,A1 .Location in patent: Page/Page column 5-7

15
[ 143314-17-4 ]
[ 106-93-4 ]
[ 111-55-7 ]
[ 65039-08-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	at 20℃; for 3h;Inert atmosphere;	Example 1 and 2: ethylene glycol diacetate; A 100 mL Schlenk flask was equipped with a magnetic stirring bar, EMIM-acetate (50.0 g, 0.293 mol), and 0.5 equivalents of 1,2-dichloroethane (14.5 g, 0.146 mol) were added at room temperature and reaction was stirred at 70C for 3h. After reaction two phases were obtained upper layer was decanted and the reaction mixture was extracted 3 times with diethyl ether, all fractions were combined and diethyl ether was removed under vacuum. The final pure product was obtained as color less liquid (90.0% yield) When 1, 2-dibromoethane was used as substrate the reaction was very fast even at room temperature and was highly exothermic. The reaction proceeds via homogeneous pathway; the pure product was distilled from the reaction mixture at 100C under reduced pressure (90.0% yield). Ethylene glycol diacetate: 1H NMR (CDCl3, 400.13 MHz): delta = 2.02 (s, 6 H, CH3), 4.2 (s, 4H, CH2); 13C NMR: delta = 20.9 (CH3), 62.3 (CH2), 170.9 (CO); FTIR (ATR mode): v = 2961 (br), 1735 (s), 1371 (m), 1213 (s), 1048 (m).

Reference： [1]Patent: EP2532646,2012,A1 .Location in patent: Page/Page column 5-7

16
[ 78-76-2 ]
[ 143314-17-4 ]
[ 105-46-4 ]
[ 65039-08-9 ]

Yield	Reaction Conditions	Operation in experiment
83%	at 20℃; for 16h;Inert atmosphere;	Examples 6 and 7: sec-butyl acetate A 50 mL Schlenk flask was equipped with a magnetic stirring bar, EMIM-acetate (20.0 g, 0.117 mol), and 1.0 equivalents of 2-bromobutane (15.9 g, 0.116 mmol) were added at room temperature and the reaction was stirred at room temperature for 16h. After reaction two phases were obtained and the upper layer (product) was decanted (83.0% yield). When 2-chlorobutane was used as substrate the reaction was stirred at 80C for 16h. After reaction two phases were obtained. To get the pure product upper layer was decanted (82.0% yield). 1H NMR (CD3CN, 400.13 MHz): delta = 0.87 (t, 3H, CH3), 1.15 (d, 3H, CH3), 1.53 (m, 2H, CH2), 4.75 (m, 1H, CH) 13C NMR: delta = 10.0 (CH3), 19.8 (CH3), 21.5 (CH3), 29.6 (CH2), 72.8 (CH), 171.3 (CO); FTIR (ATR mode): v = 2974 (br), 1733 (s), 1371 (m), 1238 (s), 1030 (m).

Reference： [1]Patent: EP2532646,2012,A1 .Location in patent: Page/Page column 5-7

17
[ 65039-08-9 ]
[ 155371-19-0 ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 4175 - 4188
[2]Cuihua Xuebao/Chinese Journal of Catalysis,2013,vol. 34,p. 769 - 780
[3]RSC Advances,2015,vol. 5,p. 22178 - 22187

19
[ 563-63-3 ]
[ 65039-08-9 ]
[ 143314-17-4 ]

Yield	Reaction Conditions	Operation in experiment
	In water; at 20℃; for 6h;	The second stage was conversion to the acetate salt: [EMIM]Br (0.50 mol) was dissolved in water (150 mL) and added slowly into Ag(CH3COO) aqueous solution (0.50 mol in 250 mL). The mixture was stirred at room temperature for 6 h, followed by filtration to remove AgBr. Charcoal was added to the filtrate in order to remove any impurities (indicated by color), then refrigerated overnight. After filtering off the charcoal, water was removed from the filtrate through rotary evaporation under vacuum at 70 C. The obtained light yellow liquid was dried in a vacuum oven for 48 h at 80 C. The synthesized [EMIM]Ac (100 mg) dissolved in D2O (0.5 mL) for 1H NMR measurement. Multiplicities are reported as s (singlet), d (doublet), t (triplet) and m (multiplet). 1H NMR (400 MHz, D2O, delta ppm): 1.38 (t, 3H, -CH3), 1.77 (s, 3H, -CH2CH3), 3.78 (s, 3H, OOCH2CH3), 4.13 (m, 2H, OOCH2CH3), 7.33 (s, 1H, -N-CH = CH-), 7.39 (s, 1H, -N-CH = CH-), 8.63 (s, 1H, -N = CH-N-).

Reference： [1]Chemical Communications,2017,vol. 53,p. 11154 - 11156
[2]Physical Chemistry Chemical Physics,2013,vol. 15,p. 20480 - 20495
[3]Carbohydrate Polymers,2015,vol. 121,p. 348 - 354

20
[ 65039-08-9 ]
[ 143314-17-4 ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 9150 - 9156
[2]Green Chemistry,2017,vol. 19,p. 2260 - 2265

21
europium(III) nitrate hexahydrate [ No CAS ]
[ 605-70-9 ]
[ 144-62-7 ]
[ 65039-08-9 ]
{(1-ethyl-3-methylimidazolium)[Eu(1,4-naphthalenedicarboxylate)(oxalate)0.5Br]n [ No CAS ]

Reference： [1]Zeitschrift fur Anorganische und Allgemeine Chemie,2014,vol. 640,p. 2472 - 2476

22
samarium(III) nitrate hexahydrate [ No CAS ]
[ 605-70-9 ]
[ 144-62-7 ]
[ 65039-08-9 ]
{(1-ethyl-3-methylimidazolium)[Sm(1,4-naphthalenedicarboxylate)(oxalate)0.5Br]n [ No CAS ]

Reference： [1]Zeitschrift fur Anorganische und Allgemeine Chemie,2014,vol. 640,p. 2472 - 2476

23
cobalt(II) nitrate hexahydrate [ No CAS ]
[ 605-70-9 ]
[ 65039-08-9 ]
[1-ethyl-3-methylimidazolium][Co(1,4-naphthalenedicarboxylate)Br] [ No CAS ]

Reference： [1]Dalton Transactions,2015,vol. 44,p. 14666 - 14672

24
[ 333-20-0 ]
[ 65039-08-9 ]
[ 331717-63-6 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane at 20℃; for 24h;

Reference： [1]Vadiyar, Madagonda M.; Patil, Sandip K.; Bhise, Sagar C.; Ghule, Anil V.; Han, Sung-Hwan; Kolekar, Sanjay S [European Journal of Inorganic Chemistry, 2015, vol. 2015, # 36, p. 5832 - 5838]

25
[ 65039-08-9 ]
[ 14075-53-7 ]
[ 143314-16-3 ]

Yield	Reaction Conditions	Operation in experiment
91%	In acetone; at 20℃; for 24h;Inert atmosphere;	K[HF4] (0.43 g, 3.4 mmol) and l-ethyl-3-meth-ylimidazolium bromide (0.50 g, 3.4 mmol) were suspended in50 ml of acetone. Afier stirring for 24 hours under argonatmosphere at ambient temperature the suspension was filtered. The solvent was removed in vacuo to obtain a lightyellow oil. The product was dried at 90 C. in vacuo for 5hours to yield 0.61 g (91%, 3.1 mmol) of EMIm[HF4].DSC (10 Kmin?): m.p.=16 C.C/H/N Analysis calc. % (found): C, 36.40 (36.32);C/H/N Analysis calc. % (found): C, 36.40 (36.32);H, 5.60 (5.58); N, 14.15 (12.90)?H NMR (25 C., CD3CN, 300.13 MHz, delta inppm): 1.42 (t, 3H, CH3), 3.82 (s, 3H, NCH3), 4.16 (q, 2H,CH2), 7.37 (m, 1H, EtNCH), 7.43 (m, 1H, MeNCH), 8.57(s, 1H, NCHN)?3C NMR (25 C., CD3CN, 300.13 MHz, delta in ppm): 15.53 (s, 1C, NCH2-CH3), 36.73 (s, 1C, NCH3), 45.80 (s, 1C, NCH2), 123.01 (s, 1C, EtNCH), 124.64 (s, 1C, MeNCH), 136.98 (s, 1C, NCHN)?B NMR (25 C., CD3CN, 96.29 MHz, delta in ppm): -1.11 (s, 1B, BF4)?9F NMR (25 C., CD3CN, 300.13 MHz, delta in ppm): -151.23 (s, 4F, BF4)IR (ATR, 32 scans, v incm?): 3163 (w), 3122 (w),2989 (w), 2949 (w), 1574 (m), 1455 (w), 1432 (w), 1392(w), 1336 (w), 1286 (w), 1170 (m), 1015 (s), 845 (m), 805(w), 753 (m), 701 (w), 648 (m), 622 (m), 598 (w)

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 4175 - 4188
[2]European Journal of Inorganic Chemistry,2016,vol. 2016,p. 1175 - 1183
[3]Patent: US2016/229874,2016,A1 .Location in patent: Paragraph 0352; 0353; 0354; 0355; 0356; 0357; 0358-0360

26
[ 127-08-2 ]
[ 65039-08-9 ]
[ 143314-17-4 ]

Yield	Reaction Conditions	Operation in experiment
	In isopropyl alcohol; at 20℃; for 36h;	(1) Preparation of 1-ethyl-3-methyl-imidazolium acetate ionic liquid. In a 250ml round bottom three-necked flask was added 0.1mol 1-ethyl-3-methylimidazolium bromide (19.1g)and potassium acetate 2.5mol (245.3g). Add 160ml of isopropyl alcohol to dissolve. At room temperature, stir for 36h. Filter to remove insolubles, the filtrate by rotary evaporation at 70 deg.C, 8h, pale yellow oil which was dissolved in 80ml of dichloromethane, and stirred at room temperature was added powdered activated carbon 17H, filtered, and washed three times with carbon tetrachloride, and the combined filtrate by rotary evaporation The solvent was removed to give a tan oil, 70 deg.C vacuum dried to yield the desired product. Take 1-ethyl-3-methyl - imidazole acetate ionic liquid 10g, add 20g 215.5 molecular weight of D- glucosamine hydrochloride. Add aqueous hydrogen peroxide solution that has a 30% mass fraction of D-glucosamine hydrochloride. After mixing in 80ml of dimethylsulfoxide, 20 deg.C reaction for 10 days.
10 g	In isopropyl alcohol; at 20℃; for 36h;	First, 1-ethyl-3-methyl-imidazole acetate ion was preparedliquid,In a 250 ml round bottom three-necked flask, 0.1 mol of 1-ethyl-3-methylimidazolium bromide was added(19.lg) and 2.5mol of potassium acetate (245.3g)160 ml of isopropanol was added to dissolve it,Stir at room temperature for 36 h. filter,Removal of insoluble material,The filtrate was steamed at 70 C for 8 h,To give a pale yellow oil,Dissolved in 80 ml of methylene chloride,And adding activated carbon powder at room temperature for 17h,Filtered, washed with carbon tetrachloride 3 times,The combined filtrates were evaporated in vacuo to remove the solvent,Yellow oil was obtained,The product was dried in vacuo at 70 C to give the desired product. 1-ethyl-3-methyl-imidazole acetate ion liquidLg,And 10 g of D-glucosamine hydrochloride having a molecular weight of 215. 5 was added,Adding equimolar amounts of boric acid with D-glucosamine hydrochloride,After mixing in 50 ml of dimethylsulfoxide, the reaction was carried out at 25 C for 48 hours. After completion of the reaction,At room temperature,20 ml of the reaction product solution,20 ml of acetonitrile were added,Extraction three times,Remove insoluble impurities,Concentrated by rotary evaporation,And allowed to stand for 10 hours to obtain deoxyfructose,Extraction agent recovery,Recovery and Reuse of Imidazole Ionic Liquids. The conversion rate of the reaction raw material D-glucosamine hydrochloride was 100%Crystallization gave the product a purity of 97%,The molar yield of deoxyfructose 60%

Reference： [1]Patent: CN105348205,2016,A .Location in patent: Paragraph 0032; 0033
[2]Patent: CN105294579,2016,A .Location in patent: Paragraph 0032

27
[ 33454-82-9 ]
[ 65039-08-9 ]
[ 145022-44-2 ]

Yield	Reaction Conditions	Operation in experiment
	In water; at 20℃; for 3.0h;	1-Ethyl-3-methylimidazolium bromide was synthesized as a precursor for [C4MIm][OTf]. 1-Methylimidazolewas distilled before use. 1-Bromoethane (7.37 mL, 46.6 mmol) was added to tetrahydrofuran solution of 1-methylimidazole (7.88 mL, 92.4 mmol) at nitrogen atmosphere in a flask equipped with a reflux condenser andmagnetic stirrer, and the solution was stirred for 2 days at room temperature. The solution was decanted andthe ionic layer was recrystallized from tetrahydrofuran and ethanol three times. The obtained solid was driedin vacuo at 313 K for more than 2 days. The obtained 1-ethyl-3-methylimidazolium bromide was successivelyused for the preparation of 1-ethyl-3-methylimidazolium trifluoromrthylsulfonate. The 1-ethyl-3-methylimidazolium bromide was dissolved in water and aqueous solution of lithium trifluoromethanesulfonate(8.73 g, 55.9 mmol) was added. After the mixture was stirred at room temperature for 3 hours, and extractedwith dichloromethane. The obtained layer was washed with water five times. The dichloromethane was thenevaporated. The resultant ionic liquid and activated carbon were added in acetonitrile, and stirred at roomtemperature over night. The solution was then filtered and evaporated. The colorless ionic liquid was thenobtained and dried in vacuo at 313 K for more than 2 days. The yield was 50.0 %.

Reference： [1]Bulletin of the Chemical Society of Japan,2016,vol. 89,p. 1106 - 1128

28
[ 65039-08-9 ]
[ 76-05-1 ]
[ 174899-65-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	With 1-hexene; dihydrogen peroxide at 25℃; for 5h;	Ionic liquids (Table 1, Entries 1-19, 21); General Procedure General procedure: A mixture of the appropriate imidazolium bromide (0.2 mol) and hex-1-ene (30 mL) was stirred in a flask, and a mixture of the appropriate protonic acid (0.2 mol) and H2O2 (0.1 mol) was added dropwise at room temperature (25 °C). After the appropriate time (Table 1), the liquid was placed in a separatory funnel and the oil phase was removed. The aqueous phase was washed with portions of CH2Cl2 (50mL) until it was colorless. Residual H2O in the product was removed by azeotropic distillation with cyclohexane. For [BzMim]PF6 (Table 1,entry 18), which has low water solubility, post-processing required only distillation and desiccation of the oil phase.
	In acetone at 20℃; for 48h; Inert atmosphere;

Reference： [1]Li, Wenxiu; Dai, Shangwu; Li, Dong; Zhang, Qinqin; Fan, Hongtao; Zhang, Tao; Zhang, Zhigang [Synthesis, 2017, vol. 49, # 5, p. 1065 - 1072]
[2]Fang, Da-Wei; Zhang, Fang; Jia, Rui; Shan, Wei-jun; Xia, Li-xin; Yang, Jia-zhen [RSC Advances, 2017, vol. 7, # 19, p. 11616 - 11625]

29
[ 75-75-2 ]
[ 65039-08-9 ]
[ 145022-45-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	With 1-hexene; dihydrogen peroxide; at 25℃; for 4.0h;	A mixture of the appropriate imidazolium bromide (0.2 mol) and hex-1-ene (30 mL) was stirred in a flask, and a mixture of the appropriate protonic acid (0.2 mol) and H2O2 (0.1 mol) was added dropwise at room temperature (25 C). After the appropriate time (Table 1), the liquid was placed in a separatory funnel and the oil phase was removed. The aqueous phase was washed with portions of CH2Cl2 (50mL) until it was colorless. Residual H2O in the product was removed by azeotropic distillation with cyclohexane. For [BzMim]PF6 (Table 1,entry 18), which has low water solubility, post-processing required only distillation and desiccation of the oil phase. 1-Ethyl-3-methylimidazolium Mesylate ([EMim]MeSO3; Table 1, Entry 1)30 Colorless liquid; yield: 38.316 g (93%). 1H NMR (500 MHz, D2O): delta = 8.72 (s, 1 H), 7.51 (s, 1 H), 7.45 (s, 1 H),4.25 (q, J = 7.5 Hz, 2 H), 3.91 (s, 3 H), 2.82 (s, 3 H), 1.52 (t, J = 7.5 Hz, 3H). 13C NMR (126 MHz, D2O): delta = 135.01, 122.97, 121.36, 44.23, 38.04, 35.12, 13.98.

Reference： [1]Synthesis,2017,vol. 49,p. 1065 - 1072

30
[ 65039-08-9 ]
[ 174899-65-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Amberlite IRN₇₈ (SUPELCO) / water 2: water

Reference： [1]Akiba, Takashi; Tsurumaki, Akiko; Ohno, Hiroyuki [Green Chemistry, 2017, vol. 19, # 9, p. 2260 - 2265]

31
[ 65039-08-9 ]
[ 145022-44-2 ]

Reference： [1]Green Chemistry,2017,vol. 19,p. 2260 - 2265

32
[ 131651-65-5 ]
[ 65039-08-9 ]
[ 174899-79-7 ]

Yield	Reaction Conditions	Operation in experiment
68%	In water at 20℃; for 2h;

Reference： [1]Gouveia, Andreia S. L.; Tomé, Liliana C.; Lozinskaya, Elena I.; Shaplov, Alexander S.; Vygodskii, Yakov S.; Marrucho, Isabel M. [Physical Chemistry Chemical Physics, 2017, vol. 19, # 42, p. 28876 - 28884]

33
lead acetate trihydrate [ No CAS ]
[ 65039-08-9 ]
[ 143314-17-4 ]

Yield	Reaction Conditions	Operation in experiment
	In water; at 20℃; for 4h;	EmimBr and lead acetate trihydrate were dissolved in deionized water at a molar ratio of about 2:1. The EmimBr solution was added dropwise to the lead acetate solution under stirring at room temperature for 4 h. After precipitation, the mixture was transferred to a refrigerator and left for 5 h for sedimentation. The filtrate was obtained by vacuum filtration while the mixture was still cool. The drying and purification procedure described above was used. Bright-yellow viscous EmimOAc was obtained and stored in a desiccator. 1H NMR (DMSO-d6): 1.31 (t, 3H), 1.59 (s, 3H), 3.86 (s, 3H), 4.18 (m, 2H), 7.74 (s, H), 7.83 (s, H), 9.73 (s, H); decomposed 180 C; purity: 98%.

Reference： [1]Cuihua Xuebao/Chinese Journal of Catalysis,2017,vol. 38,p. 879 - 888

34
[ 13755-29-8 ]
[ 65039-08-9 ]
[ 143314-16-3 ]

Yield	Reaction Conditions	Operation in experiment
	In acetone; at 20℃;	In a round bottomflask, a mixture of 1-methyl imidazole (4.1 g; 50 mmol) andethyl bromide (5.45 g, 50 mmol) was stirred at 80 C in neatcondition for 10 h. After that, neutral ionic liquid [EMIM][Br]was obtained as white solid. The reactionmixturewaswashedwith ethyl acetate four times for complete removal of n-ethylbromide and other organic compounds. It was then subjected to vacuum to obtain the pure solid [EMIM][Br]. After that,sodium tetrafluoroborate (5.3 g, 48.17 mmol) was added tothe [EMIM][Br] in acetone and stirred overnight at roomtemperature to obtain [EMIM][BF4]. The solution was filteredand acetone was removed in vacuum to obtain the pure[EMIM][BF4] as a colorless liquid.
	In methanol; at 20℃; for 24h;	General procedure: Another anion exchange reaction was carried out to achieve IL with boron tetrafluorides as a counter anion (IL-BF4) by metathesis reaction as per reported literature with minor modifications (Scheme 2). A demonstrative example for the synthesis of [RMIM]BF4 (i.e., [EMIM]BF4, [BMIM]BF4, [HMIM]BF4, [OMIM]BF4, [DMIM]BF4) and [RBZMIM]BF4 (i.e., [EBZMIM]BF4, [BBZMIM]BF4, [HBZMIM]BF4, [OBZMIM]BF4, [DBZMIM]BF4) in Scheme 2 (step-3) derivatives are as follows: 1:2 ratio of the 1-methyl-3-alkylimidazolium bromide or 1-methyl-3-alkylbenzimidazolium bromide ([RBZMIM]Br) and NaBF4 were added distinctly in to the round bottom flask containing 25mL of methanol and stirred at room temperature for 24h. Afterward, the salt was removed by filtering the reaction mixture using Whatman filter paper. Further, the filtrate was centrifuged for 10min at 3000rpm to isolate the residual salts. Solvent was evaporated under reduced pressure, vacuum dried and characterized (using 1H and 13C NMR and mass spectroscopy). The spectral details of the synthesized ILs are provided in the supplementary information Figs. S1 to S30.

Reference： [1]Journal of Chemical Sciences,2018,vol. 130
[2]Journal of Molecular Liquids,2018,vol. 268,p. 156 - 168

35
[ 2926-30-9 ]
[ 65039-08-9 ]
[ 145022-44-2 ]

Reference： [1]Journal of Solution Chemistry,2019,vol. 48,p. 125 - 141

36
[ 65039-08-9 ]
[ 118072-93-8 ]
(1-ethyl-3-methyl-1H-imidazol-3-ium) hydrogen (1-hydroxy-2-(1H-imidazol-1-yl)-1-phosphonoethyl)phosphonate [ No CAS ]

Reference： [1]ChemMedChem,2019,vol. 14,p. 1767 - 1770

37
[ 127-09-3 ]
[ 65039-08-9 ]
[ 143314-17-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	In methanol; at 40℃;	[Emim] Br (19.107 g, 0.1 mol) was placed in a 100 mL three-necked flask,Dissolve anhydrous sodium acetate (8.2g, 0.15mol) in anhydrous methanol (35mL) at 40 C.Slowly add the methanol solution of anhydrous sodium acetate to the three-necked flask using a constant pressure dropping funnel.After the dropwise addition, place it at 0 C or lower and vacuum filter.The filtrate was rotary evaporated to remove the solvent, and dried under vacuum at 80 C for 24h.The product was obtained as a pale yellow viscous liquid (14.46 g, 85%).

Reference： [1]Patent: CN110330459,2019,A .Location in patent: Paragraph 0120; 0123; 0127-0129

38
[ 1934-75-4 ]
[ 65039-08-9 ]
1-ethyl-3-methylimidazolium dicyanimide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In propan-2-one at 57℃;	2.2 (2) when raw material 1-methylimidazole detected content≤0.1% in step (1),Dissolve sodium dicyanamide in acetone, stir evenly, add it to the reaction system at room temperature,The reaction was refluxed overnight at reflux (57°C).The feeding amount in step (2) is respectively: sodium dicyanamide: 80.2g (0.9mol),1-Ethyl-3-methylimidazolium bromide: 171.9 g (0.9 mol);Post-processing: first carry out suction filtration treatment, the product filtered out is rotary evaporated to remove the solvent, then add dichloromethane to it, there is precipitation, add it several times until no precipitation is precipitated,The solid was removed by filtration, and the dichloromethane was removed by rotary evaporation.1-ethyl-3-methylimidazolium dicyanamide salt ionic liquid was obtained.After the reaction is detected by GC, the target product can be obtained by vacuum concentration, and the yield is 95% and the purity is ≥99%.Figure 3 shows the infrared spectrum of the 1-ethyl-3-methylimidazolium dicyanamide salt ionic liquid product. It can be seen from Figure 2 and Figure 3 that, compared with the N-H characteristic absorption peak of 1-methylimidazole, the characteristic absorption peak at 3300-3500 cm-1 becomes stronger, indicating that the imidazole ring is ionized,thus provedFormation of 1-ethyl-3-methylimidazolium dicyanamide salt ionic liquid.

Reference： [1]Current Patent Assignee: NINGXIA ZHUOYU NEW MATERIAL TECH CO LTD - CN114315730, 2022, A Location in patent: Paragraph 0059; 0063-0066

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	65039-08-9	MDL No. :	MFCD03427610
Formula :	C₆H₁₁BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GWQYPLXGJIXMMV-UHFFFAOYSA-M
M.W :	191.07	Pubchem ID :	2734235
Synonyms :

Num. heavy atoms :	9
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.5
Num. rotatable bonds :	1
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	43.02
TPSA :	8.81 Å²

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) :	-6.46 cm/s

Log Po/w (iLOGP) :	-2.76
Log Po/w (XLOGP3) :	1.41
Log Po/w (WLOGP) :	-2.66
Log Po/w (MLOGP) :	0.84
Log Po/w (SILICOS-IT) :	0.26
Consensus Log Po/w :	-0.58

[ CAS No. 65039-08-9 ] {[proInfo.proName]}

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[ 65039-08-9 ] Synthesis Path-Upstream 1~12

[ 65039-08-9 ] Synthesis Path-Downstream 1~38

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

Log S (ESOL) :	-2.26
Solubility :	1.05 mg/ml ; 0.00552 mol/l
Class :	Soluble
Log S (Ali) :	-1.2
Solubility :	12.1 mg/ml ; 0.0632 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.71
Solubility :	37.6 mg/ml ; 0.197 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.43

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Yield	Reaction Conditions	Operation in experiment
98%	at 40℃; for 24 h; Schlenk technique; Inert atmosphere	General procedure: The ligands (except 3) were all synthesized by adaptation of the methods of Starikova et al. [20]. A typical and generic procedure is described. Spectroscopic and analyses data are presented. N-monosubstituted azole (0.1mmol) and dry toluene were placed in a two-neck flask and stirred until a homogeneous solution was formed; then alkyl halide (0.3mmol) was added drop wise with continuous stirring. After addition of the alkyl halide, the mixture was stirred while heating at 40°C for 24h. The solvent was removed and the ligand was dried under vacuum. 2.2.2 1-Methyl-3-ethylimidazolium bromide (2) White solid. Yield (4.70 g, 98percent). IR (ATR cm^-1): 3065, 2975, 1670, 1571, 1467, 1172, 1101, 856, 789, 649, 789, 621, 417; δ_H (400 MHz, CDCl₃): 1.47 (3H, t, J 7.3 Hz, CH₃), 3.97 (3H, s, NCH₃), 4.32 (2H, q, NCH₂), 7.54 (2H, s, NCH) and 10.07 ppm (1H, s, CH); δ_C (100 MHz, CDCl₃): 15.64 (CH₃), 36.63 (NCH₃), 45.18 (NCH₂), 122.01 (NCH), 123.71 (NCH) and 136.73 ppm.; m/z (ESI) 111.5 (M⁺-Br^-). HRMS (ESI) calcd for C₆H₁₁BrN₂, 111.09222 (M⁺-Br^-); found, 111.09196 (M⁺-Br^-).
95%	at 80℃; for 0.0333333 h; Microwave irradiation	The intermediate 1-ethyl-3-methylimidazolium bromide[EMIM]Br was prepared with equimolar bromoethane(>99percent) and 1-methylimidazolium (>99percent) in a closed glass reactor and the reaction was enhanced by microwave(Milestone microwave lab station, Italy). Firstly, the reactor was heated to 80°C (80 w) during a period of 30 seconds and the temperature was kept for another 90 seconds(100 w) to complete this reaction. The forming of AlCl₃/[EMIM]Br was prepared by slow addition of known amounts of AlCl₃ (anhydrous, grain, >99percent) to the formerintermediate ([EMIM]Br) in a long beaker. The temperaturewas controlled carefully in case of decomposition of the ionic liquid
90%	at 50 - 80℃; for 4 h;	Step 1"; Synthesis of l-ethyl-3-methylimidazolium bromide; Into a flask equipped with a thermometer, a nitrogen gas inlet tube, a reflux condenser tube, a stirrer, and a dropping funnel, methylimidazole 82 g (1.0 mol) and 2-butanone(hereinafter, described as MEK) 400 g were charged. While the mixture was maintained at 50°C under nitrogen flow, ethyl bromide163.5 g (1.5 mol) was added dropwise into the mixture over 2 hours. Then, the mixture was maintained at 80°C for 2 hours and then the reaction was completed. Then, the reaction liquid was filtered to obtain l-ethyl-3-methylimidazolium bromide (hereinafter, described as EMImBr) whichwas a slight brown-white crystal. Then, this crystal was washed with MEK two times in a glove box, the inside of which was substituted with nitrogen, to obtain white EMImBr 172g (yield of 90percent) .

86%	Inert atmosphere; Schlenk technique	General procedure: The salts 15a-15e were prepared by the reported procedures. The reactions of neat alkyl halides with 1-methyl imidazole were carried out under nitrogen atmosphere. The white solid compounds were formed in the reaction mixture. These reaction mixtures were evaporated to dryness in vacuum to give white solid salts in good yield. The solid salts were highly hygroscopic in nature. All salts 15a-15e were characterized by common spectroscopic techniques.
85%	at 35℃; for 5 h;	Ionic liquid 1-ethyl-3-methylimidazolium bromidePreparation of the compound:In a 100 ml three-necked flask with a condensing reflux unit,Add 1-methylimidazole (8.2 g, 0.1 mol),Ethyl bromide (11.99 g, 0.11 mol) was stirred at 35 ° C for 5 hours.A white crystalline powder was obtained which was washed with ethyl acetate to remove ethyl bromide.Dry at 80 ° C for 3 h under vacuum. The yield was 85percent.
49.7%	at 70 - 80℃; for 10 h; Reflux	0.82g (10 mmol) 1-methylimidazole and 1.09 g (10 mmol) bromoethane were slowly added to 50 mL acetonitrile under stirring with continuous heating at 70–80C and refluxing for 10 h. It was then filtered off and recrystallized with methanol and ether, and dried under vacuum. The yield of MLDE ¢Brreached about 49.7percent. The synthesis method can be showedas the followed Scheme 2.

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