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CAS No. : | 4333-62-4 | MDL No. : | MFCD00159685 |
Formula : | C5H9IN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ARSMIBSHEYKMJT-UHFFFAOYSA-M |
M.W : | 224.04 | Pubchem ID : | 20334 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 43.3 |
TPSA : | 8.81 Ų |
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) : | -6.96 cm/s |
Log Po/w (iLOGP) : | -1.44 |
Log Po/w (XLOGP3) : | 1.0 |
Log Po/w (WLOGP) : | -3.15 |
Log Po/w (MLOGP) : | 0.67 |
Log Po/w (SILICOS-IT) : | 0.01 |
Consensus Log Po/w : | -0.58 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.32 |
Solubility : | 1.07 mg/ml ; 0.00477 mol/l |
Class : | Soluble |
Log S (Ali) : | -0.77 |
Solubility : | 37.7 mg/ml ; 0.168 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.28 |
Solubility : | 118.0 mg/ml ; 0.527 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.21 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319 | 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 |
---|---|---|
98% | In toluene; at 40℃; for 24h;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 40C for 24h. The solvent was removed and the ligand was dried under vacuum. 2.2.1 1,3-Dimethylimidazolium iodide (1) Brown solid. Yield (4.80 g, 98%) IR (ATR cm-1): 3433, 3152, 3094, 2953, 1619, 1572, 1341, 1170, 1084, 1020, 826, 748, 617; deltaH (400 MHz, CDCl3): 4.07 (6H, s, NCH3), 7.35 (2H, s, NCH) and 9.97 ppm (1H, s, CH); deltaC (100 MHz, CDCl3): 37.12 (NCH3),123.36 (NCH) and 137.76 ppm.; m/z (ESI) 96.7 (M+-I-). HRMS (ESI) calcd for C5H9IN2, 97.07657 (M+-I-); found, 97.07628 (M+-I-). |
98.8% | In ethyl acetate;Reflux; | To a solution of 10.2 g (0.12 mol) of 1-methylimidazole in 60 mL, of ethyl acetate was added 43.4 g (0.306 mol) of methyl iodide. The mixture was refluxed overnight and yellow oil separated during the course of the reaction. After cooling, the oil solidified giving 26.9 g (98.8 %) of a hygroscopic solid. Two recrystallizations from ethyl acetate afforded colourless prisms, which after drying in vacuo at 75 C had a melting point of 86.5-88 C. Anal. calcd. for C5H9N2I: C, 26.80; H, 4.05; I, 56.64; N, 12.50; found: C, 26.94; H, 4.12; I, 56.89; N, 12.37. |
85% | In propan-1-ol; at 100℃; for 19h; | 2.4.3. 1,3-Dimethylimidazolium iodide (QT-70). 1-Methylimidazole (202 mg, 2.46 mmol, 1 equiv) was dissolved in 1-propanol (2 mL) at rt and to this was added iodomethane (0.31 mL, 4.98 mmol, 2 equiv). The mixture was heated at 100 C. for 19 h, then cooled to 0 C. Et2O was slowly added with stirring resulting in a yellow precipitate that was removed by filtration and washed with Et2O (3×) and also with EtOAc (5×). High-vacuum drying gave QT-70 (470 mg, 2.10 mmol, 85%) as a yellow solid: mp 78-80 C.; 1H NMR (400 MHz, CD3OD): delta 3.93 (s, 6H), 7.56 (s, 2H), 8.87 (s, 1H); 13C NMR (100 MHz, CD3OD): delta 36.6, 124.8, 138.6; HRMS (ESI): Calcd. for C4H7N2 ([M-I-CH2]+) 83.0609. Found: 83.0593. |
82% | In neat (no solvent);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. |
75% | In toluene; at 90℃; | Under vigorous stirring, freshly distilled CH3I (40.0 mmol, 4 equiv.) was added dropwise to a solution of 1-methylimidazole (10.0 mmol) in toluene (30 mL). The mixture, already turbid, was heated at 90 C overnight. The resulted imidazolium salt was decanted from the hot solution in a separatory funnel, washed three times with toluene and dried at 70 C for 8 h under reduced pressure. The product was obtained as a brown solid with 75% yield. |
66% | In tetrahydrofuran; at -0.16℃; for 1h;Inert atmosphere; | An amount of 4.40 g (54 mmol) of 1-methylimidazole (it was purified bydistillation under reduced pressure before using.) was dissolved in 40mL anhydrousTHF. Iodomethane (15.21 g, 107 mmol) was added dropwise into the 1-methyimidazolesolution at 273 K under N2 gas atmosphere. The mixture was stirred at roomtemperature for an hour. Then, 30 mL of diethyl-ether was added into the solution.After confirming no further reprecipitation was observed by adding anotherdiethyl-ether, the solid product was collected by suction filtration. The product wassolved into the mixture of acetonitrile and ethyl acetate for the recrystallization.1,3-Dimethylimidazolium iodide, [C1mim]I, was obtained (8 g, yield 66%) ashygroscopic crystal. |
45% | In dichloromethane; at 20℃; for 16h; | To a 50 mL round bottle was added 1-methyl-1H-imidazole(1.6 mL) and dichloromethane (20mL), the mixture was sirred 10 mins, then iodomethane (1.6 mL) was added into dropwisely, the mixture was stirred at room temperature for 16 hours. after finished, the mixture was concentrated under reduced pressure, which afforded colorless oil, the oil was washed with 10 mL diethyl ester, immediately white solid was appeared, carefully removed the diethyl ester mother liquor , and repeated the purified process twice (2*10 mL diethyl ester) to afforded white solid, then the solid was dried under vaccum, which afforded 1, 3-dimethyl-1H-imidazol-3-ium iodide (NHC Precursor I) as white solid (2 g, 45%). |
at 0 - 20℃; for 147h; | 1,3-Dimethylimidazolium chloride (MMIMCl) was obtained by chemical synthesis in our laboratories. 1.7mL of iodomethane (Merck-Reagent for synthesis) was added dropwise to 2mL of distilled 1-methylimidazole (Merck-Reagent for synthesis) (1.08:1 mole proportion) under vigorous stirring at 0C for 3h. The mixture was then kept at room temperature and maintained under stirring for 6 days. The excess of iodomethane was removed by distillation and captured in an ammonium hydroxide solution. After distillation, a viscous yellow liquid of MMIMI was obtained. In order to replace iodide by chloride anions, MMIMI was passed through an ion exchange resin (Aldrich, Dorwex 1×4 chloride form). The complete exchange of iodide anion was confirmed by the absence of the UV signal at 226nm on eluted aliquots. The excess of water was removed by evaporation under reduced pressure, yielding a colorless solid of MMIMCl. | |
In acetonitrile; at 20℃; for 24h; | General procedure: Briefly, the parent amine (1-methylimidazole, 1-phenylimidazole, 1-(2-chlorophenyl)imidazole, or 1-methylbenzimidazole; 25 mmol) was quaternized with2 eq Mel or BzCI (50 mmol) in acetonitrile (100 mL) at room temperature for 24hours. The solution was then concentrated (30 mL), precipitated in diethylether (500 mL), and volatiles evaporated in-vacuo to isolate the iodide/chloride salts as an off-white powder in good yield (80%). Caffeine was quaternized with 4 eq. of Mel (100 mmol) in acetonitrile (100 mL) at 80 C for 48 hours (70%). | |
for 2.16667h;Inert atmosphere; Cooling with ice; | A 50 ml 2-neck round bottom flask equipped with a nitrogen gas induction pipe and a cooling pipe is filled with 20 ml of trichloroethane. 3g (36.54 mmol) of 1-methylimidazole is added and stirred. methyl iodide (6.22 g, 43.85 mmol) was added dropwise in an ice water bath for about 10 minutes, followed by stirring for 2 hours. after cooling at room temperature, the solution is filtered to recover the yellow salt.10 ml of trichloroethane is added to the recovered salt and washed. When the recovered salt is heated and dried at 70 C. for 4 hours under high vacuum (1 mmHg), 8.09 g of light yellow powder is 1,3-dimethylimidazolium iodide (1,3-dimethylimidazolium iodide) ) Obtain NHC ligand (complex). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; sulfur; In methanol; at 65℃; for 20h; | General procedure: A mixture of 1c (1:0 g, 4:8 mmol), sulfur (160 mg, 1.04equiv.), and K2CO3 (0:80 g, 1.2 equiv.) in MeOH (8 mL) wasrefluxed for 3 h. After removal of the solvent, the residuewas recrystallized from boiling H2O (ca. 10 mL necessaryto obtain a clear solution). The colorless product was filtered,washed with H2O (1 mL), and dried under reducedpressure to yield 0:55 g (89%). Single crystals from hot water. | |
With sulfur; potassium carbonate; In methanol; for 48h; | General procedure: All quaternized salts (10 mmol) were dissolved in MeOH (40 mL) followed by the addition of 2 eq. of elemental sulfur (20 mmol) and stirred for 10 minutes. Once a suspension was obtained, 2 eq. of potassium carbonate (20 mmol) was added and left stirring for up to 48 hours. MeOH was then fully evaporated in-vacuo and theresidue rinsed with water (3x50 mL) and recrystallized from isopropanol and dried in-vacuo to isolate off-white crystals (60%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With selenium; potassium carbonate; In ethanol; for 6h;Reflux; | General procedure: 1-Butyl-3-methylimidazolidine, chloride salt (5 mmol), selenium (5 mmol), potassium carbonate (10 mmol), ethanol or acetone (5 mL) and a magnetic stirring bar were placed in a 50 mL, two-necked flask. Then the reaction mixture was vigorously stirred under reflux for the given times (see Table 2). After the reaction was complete, the resultant mixture was filtered, and the solvent evaporated under reduced pressure. Further purification by column chromatography on silica gel gave the pure product. All the products were characterised by NMR and HRMS. |
47% | With selenium; sodium carbonate; In water; for 4h;Reflux; | General procedure: In a 50-mL, two-necked flask, 1-butyl-3-methylimidazolium chloride (5 mmol), selenium (5 mmol), Na2CO3 (10 mmol), H2O (5 mL), and a magnetic stirring bar were placed. Then, the reaction mixture was vigorous stirring under refluxing condition for 4 h. After the reaction was complete, and the resultant mixture was filtered, and the solvent evaporated under reduced pressure. Further purification by recrystallization or column chromatography on silica gel gave the pure product. All the products were characterized by NMR and HRMS. Detailed characterization of the previously known compounds from Table 2 arepresented in the Supplemental Materials. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With (tert-butyl)OK In toluene (Ar); addn. of (tert-butyl)OK (1.4 equiv.) to suspn. of 1,3-dimethyl imidazolium iodide (1 equiv.) and Karstedt's catalyst (1 equiv.) in tolueneat 0°C; stirring at room temp. for several hours; filtration on pad of Celigel (SiO2/Celite 1:1); elution with P.E./Et2O 85:15; evapn. of combined filtrates; crystn. on standing, flash chromy. (P.E./Et2O 85:15); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | General procedure: To a suspension of the imidazolium salt (1.0 molar equiv.) in dry THF (15ml) was added KOtBu (1.2 molar equiv.). After 1h, the solution was added to a solution of the metal precursor [FeI(Cp)(CO)2] (0.9 molar equiv.) in dry toluene (40ml). After stirring for 20h, the formed precipitate was separated by centrifugation, washed once with dry toluene (30ml), and then extracted with dry dichloromethane (2×30ml). Evaporation of the solvent gave the crude product, which was recrystallized by slow diffusion of hexane into dichloromethane solution to yield single crystals suitable for X-ray diffraction. 2.3.1 (eta5-C5H5)Fe(CO)2(ImMe)I (10) Complex 10 was prepared from dimethylimidazolium iodide (0.21 g, 0.90 mmol), KOtBu (0.12 g, 1 mmol), and [CpFe(CO)2I] (0.24 g, 0.8 mmol). The crude product was obtained as a brownish paste. Yield (0.12 g, 53%). IR (CH2Cl2, cm-1): 2048, 2000. upsilon(CO); deltaH (400 MHz, CDCl3): 3.92 (6H, s, CH3), 5.50 (5H, s, Cp) and 7.27 ppm (2H, s, NCH), deltaC (100 MHz, CDCl3): 40.65 (NCH3), 87.30 (Cp), 127.04 (NCH), 163.62 (C-Fe), 211.37 ppm (CO); m/z (ESI) 273.3 (M+-I-). HRMS (ESI) calcd for C12H13N2O2Fe+, 237.03264 (M+-I-), found, 237.03256 (M+-I-). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In tetrahydrofuran; for 4h;Reflux; | General procedure: General Method: To a 20 mL solution of 1.1 equivalents of nickelocene (41 mg, 0.22 mmol) in anhydrous THF, the respective imidazolium NHC precursor (0.2 mmol) was added as a solid. The resulting suspension was then refluxed for 4 h. The general method was modified for 4, 5 and 6. The reactions involving the formation of more electron-deficient 4 and 5 required 10 h at reflux with 2 equivalents of nickelocene (75 mg, 0.4 mmol). Synthesis of 6 was achieved after 16 h of reflux in the presence of 2.6 equivalents of nickelocene (98 mg, 0.52 mmol). The compounds were then purified by column chromatography. Details available in the Supporting information. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ion exchange resin (Aldrich, Dorwex 1 x 4 chloride form); | 1,3-Dimethylimidazolium chloride (MMIMCl) was obtained by chemical synthesis in our laboratories. 1.7mL of iodomethane (Merck-Reagent for synthesis) was added dropwise to 2mL of distilled 1-methylimidazole (Merck-Reagent for synthesis) (1.08:1 mole proportion) under vigorous stirring at 0°C for 3h. The mixture was then kept at room temperature and maintained under stirring for 6 days. The excess of iodomethane was removed by distillation and captured in an ammonium hydroxide solution. After distillation, a viscous yellow liquid of MMIMI was obtained. In order to replace iodide by chloride anions, MMIMI was passed through an ion exchange resin (Aldrich, Dorwex 1×4 chloride form). The complete exchange of iodide anion was confirmed by the absence of the UV signal at 226nm on eluted aliquots. The excess of water was removed by evaporation under reduced pressure, yielding a colorless solid of MMIMCl. 1H NMR: (500MHz, D2O, delta in ppm) 8.64 (s, 1H-C(2)), 7.41 (s, 2H-C(4-5)), 3.88 (s, 6H-C(6-7)). 13C NMR: (500MHz, D2O, delta in ppm) 136.49 (C(2)), 123.35 (C(4-5)), 35.57 (C(6-7)). The Scheme 1 shows the chemical structures of three ionic liquids used for the experiments. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82.6% | Complex 1 Au(CNC)Cl (40.00 mg, 0.087 mmol), N,N'-dimethylimidazolium iodide (20.61 mg, 0.092 mmol) and KOtBu (11.20 mg, 0.100 mmol) were refluxed in 25 mL CH3CN overnight under an inert atmosphere. After 24 hours, a saturated LiOSO2CF3 solution in CH3CN was added and the mixture was stirred at room temperature for another 30 minutes. The mixture was gravity filtered and the filtrate was collected. The filtrate was concentrated to about 5 mL, excess Et2O was added and the mixture was kept <10 C. for 1 day. Pale yellow solid was formed.Yield: 49.32 mg, 82.6%. Anal. Calcd for C23H19N3O3F3SAu: C, 41.13; H, 2.83; N, 6.26. Found: C, 41.06; H, 3.01; N, 6.56. 1H NMR (400 MHz, (CD3)2SO): delta 3.84 (s, 6H, -CH3), 6.94 (d, 2H, J=7.09 Hz), 7.31 (t, 2H, J=6.70), 7.37 (t, 2H, J=7.18), 7.83 (s, 2H), 7.99 (d, 2H, J=7.51 Hz), 8.06 (d, 2H, J=8.03), 8.25 (t, 1H, J=8.01). 19F NMR (400 MHz, (CD3)2SO): delta -79.32. FAB-MS (+ve, m/z): 522 [M+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54.3% | In water; at 20℃; for 2h; | General procedure: [C1mim]I (5 g, 22mmol) was dissolved in distilled water (30 mL). The solutionwas added dropwise an aqueous solution (10 mL) of potassiumbis(fluorosulfonyl)amide (Kanto Kagaku) (5 g, 23 mmol). White powder wasprecipitated immediately. The suspension was stirred for two hours at room temperature.After the temperature was up to 353 K, the white powder was melted and dissolved. Theaqueous solution had pale yellow color, then small amount of sodium sulfite was added,the color of the solution was disappeared. After the solution was cooled to roomtemperature, biphasic separation was formed, and then the lower layer was crystallized.The crystals were collected and purified by performing recrystallization from themixture of water and methanol (1 : 1). [C1mim]FSA was obtained as colorless crystals.The final product was dried under vacuum (15 Pa) at 363 K for more than 24 h, and6.04 g of the product was obtained (yield 75%). Elemental analysis calcd. forC5H9N3F2O4S2: C, 21.66; H,3.27; N, 15.15. Found: C, 21.62; H, 3.24; N, 14.85. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With silver fluoride; In water; at 20℃; for 2h; | To a stirred solution of 1-alkyl-3-methylimidazolium iodides (1 mmol) in H2O (10 ml) was added slowly a solution of AgF (1 mmol) in H2O (10 ml). After stirring at room temperature for 2 h, the mixture was filtrated and the water was evaporated under reduced pressure at room temperature. The crude residue was dissolved in anhydrous methanol. The subsequent filtration and the evaporation of the solvent under reduced pressure to give the corresponding product in quantitative yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: dibutyl phosphate With Amberlyst A-26 (OH- form) In methanol; water at 20℃; Stage #2: 1,3-dimethylimidazolim iodide In methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; at 0℃; for 1h; | 1,3-dimethylimidazolium iodide NHC ligand 1g (3.1 mmol) and tetrahydrofuran (THF) 5g (69.3 mmol) in a 100 ml round two-neck flask equipped with a gas induction tube and stirred for 10 minutes. carbon dioxide at 0 C using an ice bath aeration is performed at 40 cc / min for 1 hour to obtain the formula 8 below. solid 1,3-dimethylimidazolium carboxylate(1,3-dimethylimidazolium carboxylate) catalyst was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With potassium hexamethylsilazane; In tetrahydrofuran; at 20℃; for 20h;Sealed tube; Inert atmosphere; Glovebox; | [00159j In an inert atmosphere glovebox, (+)-diispinocampheylborane (396.3 mg, 1.384 mmol, 1 equiv.), potassium bis(trimethylsilyl)amide (289.9 mg, 1.453 mmol, 1.05 equiv.) and 1,3-dimethylimidazolium iodide (310.1 mg, 1.384 mmol, 1 equiv.) were weighed into a flame-dried nitrogen-cooled Shlenk flask. A magnetic stir bar was added and the flask was sealed with a rubber septum. The flask was removed from the glove box and connected to a Shlenk line where it was stirred under nitrogen. Dry tetrahydrofuran (20 mL) was added via cannula and the solution was stirred for 20 hours at room temperature. Solvent was removed in vacuo and the flask was reintroduced to the glovebox. The white residue was washed with pentane (3 x 2 mL). These washings were filtered through a celite plug into a vial. The residue was then washed with toluene (3 x 2 mL) and these washings were filtered through the same celite plug into a separate vial. The vials was capped and put in a freezer (- 35C) where colourless crystals formed. The crystals were washed with cold pentane (3 x lmL) and dried in vacuo to give 198 mg 1,3-dimethylimidazol-2-ylidene-di-(1S,2R,3S,58)- isopinocampheylborane (37% yield) (68 mg were recovered from the pentane washings and 130 mg were recovered from the toluene washings). [00160j ?H NMR (500 MI-Tz, CDC13, 298 K): oe 6.81 (s, 1H), 6.74 (s, 1H), 3.88 (br,6H), 2.18 (m, 1H, -CR), 2.13-2.07 (m, 2H, -CHR), 2.05-1.96 (m, 1H, -Cu), 1.92-1.83 (m,2H, -CR), 1.75-1.63 (m, 3H, -CHH, -CH, -CR), 1.59-1.52 (m, 1H, -CR), 1.43-1.34 (m, 1H, -CM), 1.32-1.23 (m, 1H, -CHR), 1.19-1.02 (m, 2H, -CM), 1.122 (s, 3H, CH3) 1.117 (s, 3H,CH3), 1.09 (overlapping s, 6H, 2xCH3), 1.08 (d, 3H, 3Jj1j= 7.0 Hz, CH3), 0.95 (br d, 2H,3J11-1= 8.5 Hz, CH2), 0.71 (br d, 2H, 3Jjj= 8.6 Hz, CH2), 0.59 (d, 3H, JHH- 7.2 Hz, CH3)(No B-H peak found). ?B NMR (128 MHz, toluene-d8, 298 K): oe -9.1 (d, JBH= 86Hz).?3C{?H} NMR (125 MHz, CDC13, 298 K, partial): oe 121.1 (NHC CH), 120.0 (NHC CH),50.8 (CH), 49.9 (CH), 45.0 (CH), 43.4 (CH), 43.1 (CH), 42.7 (CH), 39.3 (C), 39.1 (C), 37.8(NHC CH3), 37.5 (NHC CH3), 36.2 (CH2), 35.3 (CH2), 33.6 (CH2), 33.3 (CH2), 28.7 (CH3),28.5 (CH3), 23.8 (CH3), 23.4 (CH3), 23.13 (CH3), 23.11 (CH3) (No peaks observed for C-B). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In water; at 20℃; for 2h; | [C1mim]I (5 g, 22mmol) was dissolved in distilled water (30 mL). The solutionwas added dropwise an aqueous solution (10 mL) of potassiumbis(fluorosulfonyl)amide (Kanto Kagaku) (5 g, 23 mmol). White powder wasprecipitated immediately. The suspension was stirred for two hours at room temperature.After the temperature was up to 353 K, the white powder was melted and dissolved. Theaqueous solution had pale yellow color, then small amount of sodium sulfite was added,the color of the solution was disappeared. After the solution was cooled to roomtemperature, biphasic separation was formed, and then the lower layer was crystallized.The crystals were collected and purified by performing recrystallization from themixture of water and methanol (1 : 1). [C1mim]FSA was obtained as colorless crystals.The final product was dried under vacuum (15 Pa) at 363 K for more than 24 h, and6.04 g of the product was obtained (yield 75%). Elemental analysis calcd. forC5H9N3F2O4S2: C, 21.66; H,3.27; N, 15.15. Found: C, 21.62; H, 3.24; N, 14.85. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15%; 15% | General procedure: 0.340 g (1.00 mmol) of 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride was deprotonated by the addition of n-BuLi (1.00 mmol) in THF at -40C. The reaction mixture was allowed to stir for 30 min after which 0.390 g <strong>[10170-69-1]dimanganese decacarbonyl</strong> (1.00 mmol) was added. The reaction mixture turned a deep orange colour after the introduction of the metal complex and the reaction mixture was allowed to slowly warm up to room temperature. The solvent was removed in vacuo and purified via silica gel chromatography by eluting first with hexane and secondly with a hexane-DCM 1:1 mixture. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 65℃; for 18h; | Example 3 Synthesis of (NHC)PF4Ph, (2) A 2.2 M solution of n-BuLi in hexane (4.54 mL, 10 mmol) was added dropwise at -78 C. to a heterogeneous mixture of KPF5Ph (2.42 g, 10 mmol) and dimethylimidazolium iodide (2.24 g, 10 mmol) in THF (50 mL). The solution was slowly reheated at room temperature then heated for 18 h at 65 C. The volatiles were evaporated under vacuum, the solid residue was washed with several portions of water (100 mL), filtered, washed with a small portion of EtOH (10 mL), and dried under vacuum to give a white powder (1.83 g, 65%). X-ray quality crystals were obtained by slow evaporation of a solution of acetonitrile under ambient atmosphere. 1H NMR (300 MHz, CD3CN): delta 3.97 (s, 6H, CH3), 7.09 (d, JPH=3.1 Hz, 2H, CHNHC), 7.24-7.31 (m, 3H, HPh-ortho+para), 7.65-7.70 (m, 2H, HPh-meta). 31P NMR (121 MHz, CD3CN): delta-141.1 (quint, JPF=849 Hz). 19F {1H} NMR (282 MHz, CD3CN): delta -43.9 (d, JFP=849 Hz). 13C {1H} NMR (75 MHz, CD3CN): delta 39.10 (quint, JCF=4.4 Hz, CH3), 123.09 (d, JCP=9.9 Hz, CHNHC), 127.93 (d, JCP=20.3 Hz, CHPh-para), 128.26 (d, JCF=4.0 Hz, CHPh-meta), 131.49 (dquint, JCF=4.0 Hz, JCP=11.3 Hz, CHPh-para), 150.01 (dquint, JCF=43 Hz, JCP=297 Hz, CHPh-iso), 159.84 (dquint, JCF=71 Hz, JCF=334 Hz, CqNHC). HRMS (ESI+) calcd for [M-F]+: 261.0768, found: 261.0640. Anal. Calcd. for C11H13F4N2P (280.21): C, 47.15; H, 4.68. Found: C, 47.05; H, 4.57. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | A method for preparing a model compound 2 of ferrohydrogenase containing functionalized aza-bridge and azacarbin ligand,The model has the chemical formula[(mu-SCH2) 2N (C6H4OMe-p)] Fe2 (CO) 5 (L) [L = 1,3-dimethylimidazol-2-Specific preparation steps are as follows:1)In a 100mL three-necked flask equipped with a nitrogen tube and a stirring magnet,1.120 g (5.00 mmol) of 1,3-dimethylimidazolium iodide,Tetrahydrofuran 20mL,Stirred at room temperature 15min,Then, 672 mg (6.00 mmol) of potassium tert-butoxide,Stirred at room temperature for 1 h,Get pink reaction solution; 2) The reaction mixture was filtered through an anaerobic column equipped with diatomaceous earth,And rinsed with 15 mL of tetrahydrofuran,Get a red solution; 3) Under nitrogen protection,198 mg (0.40 mmol) of [(mu-SCH2) 2N (C6H4OMep)] Fe2 (CO) 6 (A) was added to the above system,Stirred at room temperature for 4h,TLC monitoring the reaction until the point of the corresponding raw materials disappear; 4) The reaction mixture was drained to dryness under reduced pressure,The residue was extracted with dichloromethane,Thin layer chromatography was then performed using methylene chloride / petroleum ether = 1: 2 (v / v) as developing solvent,Collect the main ribbon,180 mg of brown-red solid 2 was obtained,Yield 80%. |
Tags: 4333-62-4 synthesis path| 4333-62-4 SDS| 4333-62-4 COA| 4333-62-4 purity| 4333-62-4 application| 4333-62-4 NMR| 4333-62-4 COA| 4333-62-4 structure
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H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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