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CAS No. : | 65039-05-6 | MDL No. : | MFCD08276307 |
Formula : | C8H15IN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XREPTGNZZKNFQZ-UHFFFAOYSA-M |
M.W : | 266.12 | Pubchem ID : | 11448496 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.62 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 57.73 |
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) : | -6.37 cm/s |
Log Po/w (iLOGP) : | -0.51 |
Log Po/w (XLOGP3) : | 2.19 |
Log Po/w (WLOGP) : | -1.88 |
Log Po/w (MLOGP) : | 1.63 |
Log Po/w (SILICOS-IT) : | 0.89 |
Consensus Log Po/w : | 0.46 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.01 |
Solubility : | 0.261 mg/ml ; 0.000982 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.01 |
Solubility : | 2.61 mg/ml ; 0.0098 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.55 |
Solubility : | 7.53 mg/ml ; 0.0283 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 1.62 |
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 |
---|---|---|
77% | In toluene; at 80℃; for 3h;Schlenk technique; | To a 50mL Schleck tube was added 1-methyl-1H-imidazole (4.1g, 0.05 mol), 1-iodobutane (13.8g, 0.075 mol, 1.5 equiv) and distilled toluene (20 mL), the mixture were heated and stirred at 80 C oil bath for 3 hours, after reaction, all the versitile were removed under vacuo, the residue colourless oil were washed with 2-methoxy-2-methylpropane (3×20 mL), dried under vacuo, which afforded 3-butyl-1-methyl-1H-imidazol-3-ium iodide (NHC precursor G) as colorless oil orlight yellow oil (77%, 10g). |
Reflux; | General procedure: The reagentsandsolventswereuseddirectlyassuppliedcommerciallywithoutfurtherpurification excepttwokindsof1-methyl-3-alkylimidazoliumhalideILssynthesizedfromthere-actions of1-alkylhalidewith1-methylimidazoleaccordingtotheliteratureprocesses. [22] Degassed alkylhalide(alkyl ethylto amyl;XCl, I) wererefluxedwiththedistilled1-methylimi-dazole togivethetwokindsofeightILs.TheILswerewashedwithethylacetate,andthendriedunderavacuumatleastfor10h([EMI]Cl: whitesolid,[PMI]Cl:colorlessoil,[BMI]Cl:whitesolid,[AMI]Cl: colorlessoil,[EMI]I:yellowsolid,[PMI]I:yellowoil,[BMI]I: yellowoil,[PMI]I:yellowoil).ElementalanalysisofC,HandNwascarriedoutonaVarioELIIIelementalanalyzer.FT-IRspectrawerecollectedfromKBrpellets(Aldrich,499%, FT-IRgrade)witha BrukerTensor27FT-IRspectrometerintherangeof4000-400cm-1. TGAwerecarriedoutinN2 atmosphere onaSDTQ600V8.3 Build101instrumentwithaheatingrateof10 C min1 anda N2 flow rateof20cm3 min1. PXRDdataforthematerialswerecollectedatambienttemperaturewithaRigakuD/Max-3c (Japan)diffractometer(Cu-Kalpha1,2 X-radiation, lambda11.540598Aandlambda21.544426A),equippedwithanX'Celeratordetectorandaflatplate sampleholderinaBragg-Brentano para-focusingopticsconfiguration(40kV,50mA).Intensitydatawerecollectedbythestep countingmethod(stepbeing0.02) incontinuousmodeinthe rangeof5r2thetar60. FluorescencespectrawereacquiredonaHitachi F-4600 fluorescence spectrophotometerwiththeexcita-tion andemissionslitssettedto5nm. | |
In acetonitrile; at 30 - 70℃; | 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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Particularly preferred ionic liquids are selected from the group consisting of: ... 1-ethyl-3-methylimidazolium diethylphosphate, 1-n-butyl-3-methylimidazolium chloride, 1-n-butyl-3-methylimidazolium bromide, 1-n-butyl-3-methylimidazolium fluoride, 1-n-butyl-3-methylimidazolium iodide, 1-n-butyl-3-methylimidazolium hydrogensulfonate, 1-n-butyl-3-methylimidazolium sulfate, 1-n-butyl-3-methylimidazolium methanesulfonate, ... |
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. |
5.69 g | With hydrogen fluoride; In water; at 60 - 100℃; for 3h; | (1) Take 10g of 98% purity by mass of 3-methyl-1-butyl iodide was added 25mL imidazole dissolved in distilled water, was added 50mL of 45% concentration of hydrofluoric acid, sealed and heated to 60oC with stirring;(2) reaction of starting material at least sufficient 3h, then heated to 100oC, excess hydrogen fluoride was evaporated and the product gas of hydrogen chloride gas, tail gas absorption using calcium oxide, not dehydrated to give 1-butyl-3-methylimidazolium ionic liquids fluoride ;(3) not dehydrated to 1-butyl-3-methyl-fluorinated ionic liquid was diluted with distilled water is added, not dehydrated butyl-3-methyl-fluorinated ionic liquid volume of distilled water is less than 1:50, dilution was added to the AgNO3 solution, if precipitation production, continue to add 20mL hydrofluoric acid, repeating (1) and (2) step until no precipitate was produced, purified non-dehydrated 1- butyl-3 - methyl fluoride ionic liquid;(4) The dehydrated purified non-3-methyl-1-butyl fluoride at 120oC ionic liquid was dried under high vacuum at least 48h, in addition to the depth of water, in addition to hydrogen fluoride, to give a viscous liquid, of a viscous liquid testing, viscous liquid was added to distilled water, distilled water and the volume of viscous liquid is less than 50, sealed and heated to 50oC, with hydrogen detector dilution residual amount of hydrogen fluoride, if the reading is greater than> 0.1ppm, continue at 120oC under high vacuum drying in addition to hydrogen fluoride untilInspection hydrogen fluoride concentration <0.1ppm; if detected hydrogen fluoride concentration <0.1ppm, the resulting liquid is 1-butyl-3-methyl fluoride ionic liquid, weighing 5.69g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: The preparation of BiOI microspheres was carried out bysolvothermal synthesis. All reagents used were of analytical grade (AR) and used as received without additional purification. 1 mmolof bismuth nitrate pentahydrate [Bi(NO3)3.5H2O] (Sigma-Aldrich,99.0%) was dissolved in ethylene glycol (10 mL, Merck 99.5%) andpoured in a solution of 10 mL of ethylene glycol containing 1 mmolof KI (99.0% Merck). The mixture was stirred at room temperaturefor 30 min and then transferred to a 23 mL Teflon autoclave reactor.The autoclave was heated at 126 C (at autogenous pressure) for18 h andfinally cooled to room temperature. Thefinal productswere separated by vacuumfiltration and extensively washed usingdistilled water and absolute ethanol (Merck, 99.5% v/v). Thematerial obtained was dried at 60 C for 24 h. The same procedurewas used to synthesize BiOI using ionic liquid 1-butyl-3-methylimidazolium iodide ([bmim]I) as an iodide source. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | 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. |
86% | 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 |
---|---|---|
98% | With ammonium iodide;Schlenk technique; Reflux; | 1-butyl imidazole put 1.82 mmol (0.24 mL) and 2.18 mmol NH4I (317 mg) and trimethyl ortho formate 9.1mmol (1 mL) in a Schlenk reaction tube and reflux under air or N2. Confirming that the protonated imidazole disappears then removed trimethyl ortho formate remaining under vacuum, and then, a small amount of the protonated imidazole deprotonation was passed through a basic alumina dissolved in ethyl acetate. After having passed through this solution, putting them in a vacuum and the product was confirmed by NMR. Yield: 98% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N,N,N,N-tetraethylammonium tetrafluoroborate; In N,N-dimethyl-formamide; at 25℃;Inert atmosphere; Electrolysis; | General procedure: Catholyte (0.10molL-1 of ionic liquid 1a-h in 5.0mL of organic solvent) and anolyte (2.0mL same solvent/electrolyte) were separated through a porous glass frit filled with methylcellulose in DMF-Et4N-BF4. The electrolysis was carried out, under N2 atmosphere at 25C, at a constant current (J=15mA·cm-2). After the consumption of 31C, the current was switched off, the anodic compartment removed and the catholyte analyzed by cyclic voltammetry at different time intervals from the end of the electrolysis | |
In N,N-dimethyl-formamide; at 25℃;Inert atmosphere; Electrolysis; | General procedure: Catholyte (0.10 mol L1 of ionic liquid 1a-h in 5.0 mL of organicsolvent) and anolyte (2.0 mL same solvent/electrolyte) wereseparated through a porous glass fritfilled with methylcellulosein DMF-Et4N-BF4. The electrolysis was carried out, under N2atmosphere at 25 C, at a constant current (J = 15 mA cm2). Afterthe consumption of 31 C, the current was switched off, the anodiccompartment removed and the catholyte analyzed by cyclicvoltammetry at different time intervals from the end of theelectrolysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 160℃; for 120h;Autoclave; | General procedure: 2.0mmol,0.5825gCo(NO3)2 6H2O and0.50mmol,0.0831gH2BDC wereplacedinacrystallisationvialplacedina25mLteflon-lined stainless-steelautoclavemixedwith1.005g[EMI]Cl.Themixturewaskeptinsidethe furnaceat160 C for5days,andthennaturallycooledtoambient temperature.Thebluecrystalsof 1 suitable forsinglecrystalX-raydiffractionwerecollectedaftersoakclearingwithacetone. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a Schlenk flask charged with 1-butyl-3-methylimidazolium iodide (128.0mg, 0.48mmol) and Ag2O (56.0mg, 0.24mmol) was added dry CH2Cl2 (10mL), the mixture was protected from light and stirred at room temperature for 20h, before the resulting yellow solution was cannula filtered and added to a red solution of [(HMB)Ru(mu2-eta1,3-exo-syn-CH2CHCHCHO)]2(BF4)2 (200mg, 0.24mmol) in dry acetone (10mL). A solid immediately precipitated and the red suspension was stirred at room temperature protected from light for 4h, followed by filtration through a celite bed and washed with dry NO2CH3. The amber coloured solution was concentrated in vacuo to 5mL followed by addition of 20mL of dry diethyl ether and stored at-10C for 18h. The amber solution was taken to dryness resulting in a brown oil, washed with 10mL of pentane, vacuum dried and extracted with 10mL of dry toluene. Pentane (50mL) was added to the yellow toluene solution resulting in a yellow suspension which was stored at-10C for 20h, following by separation of an amber oil by decantation characterised as [(HMB)Ru(BuImMe)(eta3-CH2CHCHCOOH)](BF4) in very low yield just enough for NMR experiments. 1H NMR (CDCl3, 500MHz, ppm): 6.96 (2×d, J=1.8Hz, 1H, 4,5-Im), 4.47 (dt, J=6.7, 0.7Hz, 1H, H3-heteropentadienyl), 4.11 (m, 3H, overlap CH2-N-Im and H2-heteropentadienyl), 3.84 (s, 3H, CH3-N-Im), 3.09 (ddd, J=7.2, 1.5, 0.8Hz, 1H, H1syn-heteropentadienyl), 2.17 (s, 18H, HMB), 1.87 (dt, J=10.8, 1.1Hz, 1H, H1anti-heteropentadienyl), 1.79 (q, J=7.5Hz, 2H, CH2-CH2-N-Im), 1.34 (q, J=7.6Hz, 2H, CH2-CH2-CH2-N-Im), 0.95 (t, J=7.4Hz, 3H, CH3-(CH2)3-N-Im). 13C{1H} NMR (acetone-d6, 75MHz, ppm): 182.0 (C-Ru), 122.0 and 120.9 (C4,C5-Im), 96.0 (HMB), 92.5 (C2-heteropentadienyl), 65.7 (C3-heteropentadienyl), 52.8 (C1-heteropentadienyl), 51.7 (CH2-N-Im), 38.8 (CH2-CH2-N-Im), 33.6 (CH3-N-Im), 19.8 (CH2-CH2-CH2-N-Im), 16.4 (CH3-HMB), 13.7 (CH3-(CH2)3-N-Im). ESI-TOF-MS(+) (m/z): Calcd for [C24H37N2O2Ru]+ 487.189302, found 487.189566; error-0.540454ppm, DBE 7.5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Add to a 100 mL round bottom flaskGlyphosate 1.69g (10mmol),Methanol (40 mL) and potassium hydroxide 0.62 g (11 mmol),Magnetic stirring at 50C,After the reaction solution is clarified,1-butyl-3-methylimidazolium iodide 2.66 g (10 mmol) was added,The reaction was stirred at room temperature for 0.75 hours.Dichloromethane (3 x 20 mL) was added for extraction.After the extraction is completed,The organic phase is washed once with saturated saline solution.Distilled and washed onceRotary evaporation,And dried in a vacuum drying oven to give a yellow oily liquid,Yield 90%. |
Tags: 65039-05-6 synthesis path| 65039-05-6 SDS| 65039-05-6 COA| 65039-05-6 purity| 65039-05-6 application| 65039-05-6 NMR| 65039-05-6 COA| 65039-05-6 structure
[ 171058-18-7 ]
1-decyl-3-methylimidazolium chloride
Similarity: 0.93
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H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
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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