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CAS No. : | 36443-80-8 | MDL No. : | MFCD07784451 |
Formula : | C11H13ClN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FCRZSGZCOGHOGF-UHFFFAOYSA-M |
M.W : | 208.69 | Pubchem ID : | 10560335 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 11 |
Fraction Csp3 : | 0.18 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 59.63 |
TPSA : | 8.81 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.77 cm/s |
Log Po/w (iLOGP) : | -3.28 |
Log Po/w (XLOGP3) : | 2.54 |
Log Po/w (WLOGP) : | -1.64 |
Log Po/w (MLOGP) : | 1.93 |
Log Po/w (SILICOS-IT) : | 1.51 |
Consensus Log Po/w : | 0.21 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.18 |
Solubility : | 0.137 mg/ml ; 0.000655 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.37 |
Solubility : | 0.886 mg/ml ; 0.00425 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.89 |
Solubility : | 0.268 mg/ml ; 0.00128 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.44 |
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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | at 100℃; Microwave irradiation; | |
95% | In toluene for 72h; Heating; | |
95% | In acetonitrile for 48h; Inert atmosphere; Reflux; |
95% | In toluene at -0.16 - 69.84℃; for 32.5h; | |
94% | In neat (no solvent) for 2h; Milling; | |
91% | Heating; | |
90% | In tetrahydrofuran for 24h; Schlenk technique; Reflux; | |
86% | With potassium carbonate In acetonitrile at 70℃; for 72h; | |
84% | In tetrahydrofuran Reflux; | |
78% | at 40 - 110℃; for 5h; | Benzyl chloride (0.4 mol) was dropped into methylimidazole (0.4 mol), stirred at 40 °C. The mixture was stirred for 5 h at 70-110 °C. The obtained crude 1-benzyl-3-methylimidazolium chloride, [Bzlmim]Cl, in the form of a light-orange viscous oil was dissolved in 70 cm3 acetonitrile and washed with diethyl ether (3 × 40 cm3), ethyl acetate (4 × 20 cm3), and again with diethyl ether (4 × 50 cm3), and finally with hexane (4 × 50 cm3). The product was left to stand over the hexane phase overnight to crystallize. The solid form was dried by nitrogen flow in a Schlenk apparatus to reach a constant weight. The product was obtained in the form of an off-white powder with 78% yield. |
at 80℃; for 72h; | ||
In acetonitrile at 24.84℃; | ||
In toluene | ||
In toluene | ||
at 150℃; for 0.5h; Microwave irradiation; Cooling; neat (no solvent); | ||
In toluene at 109.84℃; for 24h; | ||
In toluene for 24h; Reflux; | ||
In toluene for 24h; Reflux; | ||
In toluene | ||
In toluene for 24h; Reflux; | ||
In toluene at 80℃; for 24h; | ||
With sodium iodide In acetone at 20℃; for 12h; Schlenk technique; | ||
In chloroform at 20℃; for 5h; | 13.1 (1) Synthesis of Intermediate (b) Example 13 Synthesis of Compound B-13 (1) Synthesis of Intermediate (b) In 100 g of chloroform, 30 g of benzyl chloride was dissolved, and to this, 20 g of 1-methylimidazole was added dropwise. The contents were stirred at room temperature. After 5 hours, the disappearance of the raw materials was confirmed by HPLC, and a 50% chloroform solution of Intermediate (b) was obtained. | |
at 80℃; for 3h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In water at 20℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In dichloromethane under Ar, in absence of light; mixt. of imidazolium salt and AgOC(CF3)3 in CH2Cl2 stirred at room temp. for 2 h; Pd complex added; stirred at room temp. for 2 h; soln. column chromd. (silica gel, acetone (5%)-CH2Cl2); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In acetonitrile under Ar, in absence of light; mixt. of imidazolium salt and AgOC(CF3)3 in MeCN stirred at room temp. for 2 h; Ir complex and NaI added; heated at 60°C and stirred for 5 h; cooled to room temp.; filtered through Celite; solvent removed under vac.; purified by column chromy. (silica gel, acetone (2%)-heptane); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In dichloromethane under Ar, in absence of light; mixt. of imidazolium salt and AgOC(CF3)3 in CH2Cl2 stirred at room temp. for 2 h; Au complex added; stirred for 2h; cooled to room temp.; filtered through Celite; solvent removed under vac.; purified by column chromy. (silica gel, CH2Cl2); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In acetonitrile under Ar, in absence of light; mixt. of imidazolium salt and AgOC(CF3)3 in MeCN stirred at room temp. for 2 h; soln. filtered through Celite; solvent removed under vac.; repptd. from CH2Cl2-ether; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In dichloromethane under Ar, in absence of light; mixt. of imidazolium salt and AgOC(CF3)3 in CH2Cl2 stirred at room temp. for 2 h; soln. of Ru complex in CH2Cl2 added; stirred at room temp. for 2 h; solvent removed under vac.; purified by column chromy. (silica gel, acetone (20%)-pentane); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sulfuric acid at -3.16 - 69.84℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With Ag(OC(CF3)3) In acetonitrile mixt. of Ag compd. (0.37 mmol) and ligand (0.25 mmol) in MeCN stirred atroom temp. for 2 h, Ir compd. (0.13 mmol) ans NaI (1 mmol) added, mixt. heated to 60°C for 5 h; cooled, filtered, evapd. (vac.), chromd. (SiO2, 2% acetone/heptane), elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
> 99 %Spectr. | at 169.84℃; for 8h; Autoclave; Neat (no solvent); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In melt chloride was added to Al compd. at room temp.; heated under flow of N2; heated to 180°C and stirred for 2 h; washed-centrifuged with isopropanol; dried at 60°C overnight; ground; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid | ||
Multi-step reaction with 2 steps 1: sulfuric acid 2: chlorosulfonic acid / dichloromethane | ||
With sulfuric acid |
With sulfuric acid | ||
With sulfuric acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.17 g | In acetone at 20℃; Sonication; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27.35 g | In acetonitrile at 20℃; Sonication; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.15 g | With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.082 g | With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With sodium hypochlorite; sodium hydroxide In tetrahydrofuran at 20℃; for 0.166667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol ionic liquid prepd. by mixing hot ethanolic solns. of FeCl3*6H2O and imidazolium chloride; mixt. heated with stirring for 10-15 min; ethanol evapd. under vac.; ionic liquid washed with cold dry ether and dried under vac. over P2O5 for d; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With chlorosulfonic acid In dichloromethane at 69.84℃; for 12h; | |
With chlorosulfonic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dichloromethane 2: chlorosulfonic acid / dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dichloromethane 2: chlorosulfonic acid / dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile for 24h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 149.84℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To the obtained [Bzlmim]Cl an equivalent amount of aluminium chloride was added slowly while the mixture was constantly stirred. The obtained 1-benzyl-3-methylimidazolium chloroaluminate, liquid during synthesis, crystallized in the form of an off-white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | In neat (no solvent) for 0.166667h; Milling; | |
In dichloromethane for 12h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; selenium / methanol / 24 h / Schlenk technique; Reflux 2: iodine / dichloromethane / 3 h / 0 - 20 °C / Schlenk technique; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; selenium / methanol / 24 h / Schlenk technique; Reflux 2: lactoperoxidase; dihydrogen peroxide; potassium iodide / methanol; aq. phosphate buffer / 20 °C / pH 7.4 / Enzymatic reaction |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; sulfur In methanol for 24h; Schlenk technique; Reflux; | ||
With potassium carbonate; sulfur In methanol for 24h; Reflux; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With selenium; potassium carbonate In methanol for 24h; Schlenk technique; Reflux; | ||
With selenium; potassium carbonate In methanol for 24h; Reflux; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; sulfur / methanol / 24 h / Reflux; Schlenk technique 2: 360 h / 35 °C / Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; sulfur / methanol / 24 h / Reflux; Schlenk technique 2: 360 h / 35 °C / Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; sulfur / methanol / 24 h / Reflux; Schlenk technique 2: 360 h / 35 °C / Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; sulfur / methanol / 24 h / Reflux; Schlenk technique 2: 360 h / 35 °C / Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; sulfur / methanol / 24 h / Reflux; Schlenk technique 2: 360 h / 35 °C / Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; sulfur / methanol / 24 h / Reflux; Schlenk technique 2: 360 h / 35 °C / Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; selenium / methanol / 24 h / Reflux; Schlenk technique 2: 360 h / 35 °C / Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; selenium / methanol / 24 h / Reflux; Schlenk technique 2: 360 h / 35 °C / Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; selenium / methanol / 24 h / Reflux; Schlenk technique 2: 360 h / 35 °C / Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; selenium / methanol / 24 h / Reflux; Schlenk technique 2: 360 h / 35 °C / Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; selenium / methanol / 24 h / Reflux; Schlenk technique 2: 360 h / 35 °C / Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; selenium / methanol / 24 h / Reflux; Schlenk technique 2: 360 h / 35 °C / Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform; water at 20℃; for 3h; | 13.2 (2) Synthesis of Compound B-13 (2) Synthesis of Compound B-13 To 6.3 g of the 50% chloroform solution of Intermediate (b) obtained in (1), 6.1 g of sodium tetraphenylborate (available from NACALAI TESQUE, INC.) and 50 g of ion-exchanged water were added and stirred for 3 hours at room temperature. An organic layer was washed with 50 g of ion-exchanged water three times. The organic layer was concentrated and the solvent was evaporated, after which the residue was subjected to silica gel chromatography to obtain a white solid. It was confirmed by 1H-NMR that this white solid was Compound B-13. The structure of Compound B-13 was described in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With potassium <i>tert</i>-butylate In dichloromethane at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11.5% | With selenium; hydrazine hydrate; sodium stannate trihydrate at 150℃; for 144h; Autoclave; | For the synthesis of 2: A mixture of Na2SnO3·3H2O (0.267g, 1mmol), Se powder (0.198g, 2.5mmol) and 0.200mL en in 1g [Bzmim]Cl was sealed in a 20mL Teflon-lined stainless-steel autoclave at 150°C for 6days, followed by slowly cooling to room temperature under a cooling rate of ~5.4Kh-1. The product was washed with N,N-dimethylformamideand ethanol for several times. Red block-like crystals of 2 were obtained by manually selection (Yield: 0.048g, 11.5% based on Sn). Elemental analysis: calcd. (%) for C22H26N4Se7Sn3: C 21.05, H 2.09, N 4.46; found: C 20.37, H 2.13, N 4.45. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone at 20℃; for 48h; Inert atmosphere; | ||
In acetone at 20℃; for 96h; Inert atmosphere; | 2.2. Synthetic protocol for ILs General procedure: ILswere synthesized by procedure described earlier [28]. 0.5 molof chloride-based reactant IL (1-ethyl-3-methylimidazolium, Nbutylpyridinium,1-benzyl-3-methylimidazolium, 1-butyl-3-methylimidazolium, 1-butyl-1methylpyrrolidinium, morpholiniumand (vinylbenzyl)trimethylammonium) was taken in round bottomflask and 25 mL of acetone was further poured inside. Then 0.5 molof Na-salt of 2-acrylamido-2-methyl-1-propanesulfonic acid wastransferred to reaction mixture. The resultant mixture wasmagnetically stirred at ambient temperature under inert atmospherefor 4 days. The vacuum filtration of the mixture was doneand solvent in the filtrate was evaporated. The respective ILs obtainedafter evaporation of solvent were dissolved in DCM andextracted thrice with 10mL of cold water to get rid of traces of NaClissued from metathesis reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With tellurium tetrachloride In acetonitrile at 120℃; for 96h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With potassium carbonate In tetrahydrofuran; acetonitrile at 50℃; for 24h; | 2.3. Synthesis of palladium PEPPSI-type complexes with differentcarbene ligands [PdCl2(NHC)(imidazole)]. Method B General procedure: Palladium (II) complex with 1-methylimidazole ligands[PdCl2(1-methylimidazole)2] (0.5 mmol, 0.17 g), K2CO3 (1.5 mmol,0.21 g), MgSO4 (0.2 g, for drying), an appropriate imidazoliumchloride (0.65 mmol) and finally a mixture of solvents CH3CN:THF(8 ml: 5 ml) were placed in a round-bottom flask equipped with astirring bar. The flask was capped with a rubber septum. Themixture was heated in the oil bath for 24 h at 50 °C in the air atmosphere.During that time, the color changed from yellow togreenish. After the reaction, the cooled down mixture was filtratedto remove inorganic salts. Then, the yellow solutionwas evaporatedunder vacuum and the resulting oily residue was dissolved in aminimum amount of acetone. Next, 10 ml of water was slowlyadded to the yellow solution and clouding of the mixture wasobserved. The mixture was left to evaporate acetone and to enablesedimentation of the formed precipitate. After that time, waterwith excess of the imidazolium chloride and 1-methylimidazolewas decanted. The obtained product was washed with the waterand dried under vacuum. The complexes 2f and 2 g were obtainedfrom the appropriate imidazole and the precipitated solids requiredadditional washing with ethyl alcohol and diethyl ether. One of theobtained complexes [PdCl2(IMes)(1-methylimidazole)] (2e) wasdescribed in the literature [7b]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Stage #1: copper(l) chloride With sodium hexamethyldisilazane In tetrahydrofuran at 20℃; for 24h; Stage #2: 1-benzyl-3-methylimidazolium chloride In tetrahydrofuran; dichloromethane for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide at 126.84℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 0.77 mol 2: 0.36 mol 3: 0.55 mol 4: 0.98 mol | With potassium hydroxide In water at 60℃; for 264h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water at 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water at 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
...cylimidazolium formate, 1-benzyl-3-(2-ethylhexyl)imidazolium formate, 1,3-didodecylimidazolium formate, 1-dodecyl-3-octadecylimidazolium formate, 1-benzyl-3-dodecylimidazolium formate, 1,3-dioctadecylimidazolium formate, 1-benzyl-3-octadecylimidazolium formate, 1,3-dibenzylimidazolium formate,1,3-dimethylimidazolium acetate, 1-ethyl-3-methylimidazolium acetate, 1-butyl-3-methylimidazolium acetate, 1-methyl-3-octylimidazolium acetate, 1-methyl-3-(2-ethylhexyl)imidazolium acetate, 1-dodecyl-3-methylimidazolium acetate, 1-methyl-3-octadecylimidazolium acetate, 1-benzyl-3-methylimidazolium acetate, 1,3-dibutylimidazolium acetate, 1-butyl-3-ethylimidazolium acetate, 1-butyl-3-octylimidazolium acetate, 1-butyl-3-(2-ethylhexyl)imidazolium acetate, 1-butyl-3-dodecylimidazolium acetate, 1-butyl-3-octadecylimidazclium acetate, 1-benzyl-3-butylimidazolium acetate, 1,3-dioctylimidazolium acetate, 1-ethyl-3-octylimidazolium acetate, 1-octyl-3-(2-ethylhexyl)imidazolium acetate, 1-dodecyl-3-octylimidazolium acetate, 1-octyl-3-octadecylimidazolium acetate, 1-benzyl-3-octylimidazolium acetate, 1,3-bis(2-ethylhexyl)imidazolium acetate, 1-ethyl-3-(2-ethylhexyl)imidazolium acetate, 1-(2-ethylhexyl)-3-dodecylimidazolium acetate, 1-(2-ethylhexyl)-3-octadecylimidazolium acetate, 1-benzyl-3-(2-ethylhexyl)imidazolium acetate, 1,3-didodecylimidazolium acetate, 1-dodecyl-3-octadecylimidazolium acetate, 1-benzyl-3-dodecylimidazolium acetate, 1,3-dioctadecylimidazolium acetate, 1-benzyl-3-octadecylimidazolium acetate, 1,3-dibenzylimidazolium acetate, 1,3-dimethylimidazolium lactate, 1-ethyl-3-methylimidazolium lactate, 1-butyl-3-methylimidazolium lactate, 1-methyl-3-octylimidazolium lactate, 1-methyl-3-(2-ethylhexyl)imidazolium lactate, 1-dodecyl-3-methylimidazolium lactate, 1-methyl-3-octadecylimidazolium lactate, 1-benzyl-3-methylimidazolium lactate, 1,3-dibutylimidazolium lactate, 1-butyl-3-ethylimidazolium lactate, 1-butyl-3-octylimidazolium lactate, 1-butyl-3-(2-ethylhexyl)imidazolium lactate, 1-butyl-3-dodecylimidazolium lactate, 1-butyl-3-octadecylimidazolium lactate, 1-benzyl-3-butylimidazolium lactate, 1,3-dioctylimidazolium lactate, 1-ethyl-3-octylimidazolium lactate, 1-octyl-3-(2-ethylhexyl)imidazolium lactate, 1-dodecyl-3-octylimidazolium lactate, 1-octyl-3-octadecylimidazolium lactate, 1-benzyl-3-octylimidazolium lactate, 1,3-bis(2-ethylhexyl)imidazolium lactate, 1-ethyl-3-(2-ethylhexyl)imidazolium lactate, 1-(2-ethylhexyl)-3-dodecylimidazolium lactate, 1-(2-ethylhexyl)-3-octadecylimidazolium lactate, 1-benzyl-3-(2-ethylhexyl)imidazolium lactate, 1,3-didodecylimidazolium lactate, 1-dodecyl-3-octadecylimidazolium lactate, 1-benzyl-3-dodecylimidazolium lactate, 1,3-dioctadecylimidazolium lactate, 1-benzyl-3-octadecylimidazolium lactate, 1,3-dibenzylimidazolium lactate, 1,3-dimethylimidazolium hydrogen carbonate, 1-ethyl-3-methylimidazolium hydrogen carbonate, 1-butyl-3-methylimidazolium hydrogen carbonate, 1-methyl-3-octylimidazolium hydrogen carbonate, 1-methyl-3-(2-ethylhexyl)imidazolium hydrogen carbonate, 1-dodecyl-3-methylimidazolium hydrogen carbonate, 1-methyl-3-octadecylimidazolium hydrogen carbonate, 1-benzyl-3-methylimidazolium hydrogen carbonate, 1,3-dibutylimidazolium hydrogen carbonate, 1-butyl-3-ethylimidazolium hydrogen carbonate, 1-butyl-3-octylimidazolium hydrogen carbonate, 1-butyl-3-(2-ethylhexyl)imidazolium hydrogen carbonate, 1-butyl-3-dodecylimidazolium hydrogen carbonate, 1-butyl-3-octadecylimidazolium hydrogen carbonate, 1-benzyl-3-butylimidazolium hydrogen carbonate, 1,3-dioctylimidazolium hydrogen carbonate, 1-ethyl-3-octylimidazolium hydrogen carbonate, 1-octyl-3-(2-ethylhexyl)imidazolium hydrogen carbonate, 1-dodecyl-3-octylimidazolium hydrogen carbonate, 1-octyl-3-octadecylimidazolium hydrogen carbonate, 1-benzyl-3-octylimidazolium hydrogen carbonate, 1,3-bis(2-ethylhexyl)imidazolium hydrogen carbonate, 1-ethyl-3-(2-ethylhexyl)imidazolium hydrogen carbonate, 1-(2-ethylhexyl)-3-dodecylimidazolium hydrogen carbonate, 1-(2-ethylhexyl)-3-octadecylimidazolium hydrogen carbonate, 1-benzyl-3-(2-ethylhexyl)imidazolium hydrogen carbonate, 1,3-didodecylimidazolium hydrogen carbonate, 1-dodecyl-3-octadecylimidazolium hydrogen carbonate, 1-benzyl-3-dodecylimidazolium hydrogen carbonate, 1,3-dioctadecylimidazolium hydrogen carbonate, 1-benzyl-3-octadecylimidazolium hydrogen carbonate, 1,3-dibenzylimidazolium hydrogen carbonate, 1,3-dimethylimidazolium chloride, 1-ethyl-3-methylimidazolium chloride, 1-butyl-3-methylimidazolium chloride, 1-methyl-3-octylimidazolium chloride, 1-methyl-3-(2-ethylhexyl)imidazolium chloride, 1-dodecyl-3-methylimidazolium chloride, 1-methyl-3-octadecylimidazolium chloride, 1-benzyl-3-methylimidazolium chloride, 1,3-dibutylimidazolium chloride, 1-butyl-3-ethylimidazolium chloride, 1-butyl-3-octylimidazolium chloride, 1-butyl-3-(2-ethylhexyl)imidazolium chloride, 1-butyl-3-dodecylimidazolium chloride, 1-butyl-3-octadecylimidazolium chloride, 1-benzyl-3-butylimidazolium chloride, 1,3-dioctylimidazolium chloride, 1-ethyl-3-octylimidazolium chloride, 1-octyl-3-(2-ethylhexyl)imidazolium chloride, 1-dodecyl-3-octylimidazolium chloride, 1-octyl-3-octadecylimidazolium chloride, 1-benzyl-3-octylimidazolium chloride, 1,3-bis(2-ethylhexyl)imidazolium chloride, 1-ethyl-3-(2-ethylhexyl)imidazolium chloride, 1-(2-ethylhexyl)-3-dodecylimidazolium chloride, 1-(2-ethylhexyl)-3-octadecylimidazolium chloride, 1-benzyl-3-(2-ethylhexyl)imidazolium chloride, 1,3-didodecylimidazolium chloride, 1-dodecyl-3-octadecylimidazolium chloride, 1-benzyl-3-dodecylimidazolium chloride, 1,3-dioctadecylimidazolium chloride, 1-benzyl-3-octadecylimidazolium chloride, 1,3-dibenzylimidazolium chloride, 1,3-dimethylimidazolinium formate, 1,3-dimethylimidazolinium acetate, 1,3-dimethylimidazolinium lactate, 1,3-dimethylimidazolinium hydrogen carbonate, 1,3-dimethylimidazolinium chloride, 1-butyl-3-methylimidazolinium formate, 1-butyl-3-methylimidazolinium acetate, 1-butyl-3-methylimidazolinium lactate, 1-butyl-3-methylimidazolinium hydrogen carbonate, 1-butyl-3-methylimidazolinium chloride, 1-methyl-3-octylimidazolinium formate, 1-methyl-3-octylimidazolinium acetate, 1-methyl-3-octylimidazolinium lactate, 1-methyl-3-octylimidazolinium hydrogen carbonate, 1-methyl-3-octylimidazolinium chloride, |
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