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[ CAS No. 79917-90-1 ] {[proInfo.proName]}

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Chemical Structure| 79917-90-1
Chemical Structure| 79917-90-1
Structure of 79917-90-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 79917-90-1 ]

CAS No. :79917-90-1 MDL No. :MFCD03095425
Formula : C8H15ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :FHDQNOXQSTVAIC-UHFFFAOYSA-M
M.W : 174.67 Pubchem ID :2734161
Synonyms :

Calculated chemistry of [ 79917-90-1 ]

Physicochemical Properties

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 : 49.56
TPSA : 8.81 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : -3.29
Log Po/w (XLOGP3) : 2.13
Log Po/w (WLOGP) : -1.88
Log Po/w (MLOGP) : 1.32
Log Po/w (SILICOS-IT) : 0.89
Consensus Log Po/w : -0.17

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.4
Solubility : 0.69 mg/ml ; 0.00395 mol/l
Class : Soluble
Log S (Ali) : -1.95
Solubility : 1.98 mg/ml ; 0.0113 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.55
Solubility : 4.95 mg/ml ; 0.0283 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.55

Safety of [ 79917-90-1 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P501-P273-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P310+P330-P405 UN#:2811
Hazard Statements:H301-H315-H319-H401 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 79917-90-1 ]

* 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.

  • Upstream synthesis route of [ 79917-90-1 ]
  • Downstream synthetic route of [ 79917-90-1 ]

[ 79917-90-1 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 616-47-7 ]
  • [ 109-69-3 ]
  • [ 79917-90-1 ]
YieldReaction ConditionsOperation in experiment
92% at 90℃; Schlenk technique To a 50ml Schleck tube was added 1-methyl-1H-imidazole (4.1g, 0.05 mol), 1-chlorobutane (9.2g, 0.1 mol, 2 equiv) and distilled toluene (20 ml), the mixture were heated and stirred at 90 °C oil bath for overnight, after reaction, all the versitile were removed under vacuo. the residue were washed with 2-methoxy-2-methylpropane (3* 20 ml), dried under vacuo, which afforded 3-butyl-1-methyl-1H-imidazol-3-ium chloride (NHC precursor E) as white solid (92percent, 8g)
90% at 40℃; for 24 h; 1) N-Methylimidazole (4 g, 48.7 mmol)In a single-necked flask,And then weighed1-Chloromethane6.68 g (72.2 mmol)(The molar ratio of 1-methyl chloride to N-methyl imidazole was about 1.48: 1). After the dropwise addition, the reaction was carried out at 40 ° C for 24 hours. The reaction was monitored by thin layer chromatography , The excess of 1-methyl chloride distillation, the white solid is chlorinated 1-butyl-3-methyl imidazole, the yield of 90percent;
90% at 150℃; Microwave irradiation In a MW vial, 4 mL of 1-methylimidazole(0.0484 mol) and 7.6 mL of 1-chlorobutane (0.0726 mol) were consecutively added; then, the mixturewas irradiated (200 W) at 150 °C for 25 min. Then, the supernatant 1-chlorobutane was removedand the mixture was then washed with hexane and diluted with CH2Cl2 to be transferred in a roundbottom flask for the removal of solvent under vacuum. The desired product 5 was obtained in 90percentyield. 1H-NMR (200 MHz, CDCl3, ppm): δ = 9.71 (s, 1H), 7.99 (m, 1H), 7.89 (m, 1H), 4.24 (t, 2H,J = 7.0 Hz), 3.91 (s, 3H), 1.77 (m, 2H), 1.30 (m, 2H), 0.88 (t, 3H, J = 7.2 Hz).
88.6% for 48 h; Reflux Synthesis of 1-butyl-3-methylimidazolium chloride: A mixture of 1-methylimidazole (70.0 g, 0.853 mol), ethanenitrile (50 mL) and 1-chlorobutane (102 g, 1.10 mol) are heated under reflux with vigorous stirring for 48 hrs. 1-chlorobutane (99.5percent) is sourced from a commercial supplier (Sigma-Aldrich). Volatile substances are removed in a first step under reduced pressure (ca. 50° C., 20 mbar), and finally, in vacuo (ca. 80° C., 0.01 mbar) during 16 hrs, yielding 1-butyl-3-methylimidazolium chloride ([C4mim]Cl, 131.8 g, 88.6percent) as a pale yellow viscous liquid which crystallizes upon cooling to room temperature.
88% at 60 - 65℃; for 24 h; An amount of 1-methylimidazole (10 mmol, 1.745 g) and n-butylchloride (11 mmol, 1.018 g) were sequentially added into a 25 mL round-bottom flask assembled with the condenser. The reaction mixture was stirred magnetically with 250 rpm speed at 60–65 °C for 24 h. After cooling down to room temperature, the reaction mixture was washed with diethyl ether(5 x 10 mL) until no trace of n-butyl chloride, as well as 1-methylimidazole in a solution of diethylether were detected by thin layer chromatography (TLC) and gas chromatography (GC). The othersolution containing recyclable [Bmim]Cl was evaporated under reduced pressure at 80 °C for 30 minto afford a light yellow liquid in high yield (88percent). The identity and purity of [Bmim]Cl obtainedwere analyzed by 1H-NMR, 13C-NMR and LC/MS spectroscopy. In continuation of the preparationof [Bmim]Cl*2AlCl3, an amount of aluminum chloride (4 mmol, 0.534 g) was added slowly into a10 mL round-bottom flask containing [Bmim]Cl (2 mmol, 0.349 g). After that, the reaction mixturewere stirred magnetically at room temperature for 12 h. The identity and purity of acidic catalyst,[Bmim]Cl*2AlCl3, were checked by 1H-NMR and integrated as follows: 1H-NMR (500 MHz, D2O): δ (ppm) 8.65 (s, 1H), 7.43 (s,1H), 7.38 (s, 1H), 4.14 (t, J = 7.0 Hz, 2H), 3.84 (s, 3H), 1.77–1.82 (m, 2H),1.23–1.30 (m, 2H), 0.87 (t, J = 7.5 Hz, 3H).
86% at 110℃; for 24 h; To a vigorously stirred solution of 1-methylimidazole (1.25 mol) in toluene (125 mL) at 0 °C, 1-chlorobutane (1.38 mol) was added.
The solution was heated to reflux at 110 °C for 24 h, after which it was placed in a freezer at - 20 °C for 12 h.
The toluene was decanted and the remaining viscous oil/semi-solid was recrystallized from acetonitrile.
Again it was repeatedly recrystallized from ethyl acetate to yield a white crystalline solid, which was further dried under reduced pressure to give [Bmim]Cl in approximately 86percent yield. 1H NMR (400 MHz, DMSO-d6): δ = 10.54 (1H, s), 7.55 (1H, m), 7.40 (1H, m), 4.26 (2H, t, J = 7.3 Hz), 4.11 (3H, s), 1.82 (2H, m), 1.30 (2H, m), 0.89 (3H, t, J = 7.3 Hz).
Chloride ion is 21.10 wtpercent
85% at 80℃; 1-Butyl-3-methylimidazolium chloride was prepared from the reaction of N-methylimidazole with n-butylchloride at 80 °C under neat conditions.
82% at 75℃; for 48 h; Inert atmosphere 1-butyl-3-methylimidazolium chloride [bmim][Cl] synthesized accordingto organic synthesis [39]. A mixture of 1-methylimidazole(1 eq) and 1-chlorobutane (1.3 eq) in dry acetonitrile was stirred at75 °C for 48 h under nitrogen.The mixture was cooled to room temperature.The volatile material was removed under reduced pressure andthe remaining light-yellow oil dissolved in appropriate acetonitrileand added dropwise to a flask containing dry ethyl acetate dry ethyl acetatecontaining flask to give [bmim][Cl] as a white crystal in approximately82percent yeild.
80% Reflux; Inert atmosphere Two chloride-based ionic liquids, [BMIM]Cl and [AMIM]Cl, were synthesized according to the literature methods [10,11], respectively. Reactions were carried out under nitrogen atmosphere and followed by ESI-MS and 1H NMR. Produced ILs were dried overnight in a high vacuum at 50–70 °C and stored in a desiccator. Water content of the IL determined by the Mettler Toledo DL36 Karl Fischer coulometer was <0.1percent (w/w). (0012) [BMIM]Cl was prepared from butyl chloride (159.5 g, 1.72 mol) and N-methylimidazole (103.0 g, 1.25 mol) in a 500 ml flask by mixing and refluxing until all methylimidazole had reacted (24–48 h). The crude product was then recrystallized from an ethyl acetate–acetonitrile mixture (55:45). The yield of white [BMIM]Cl was 174.8 g (80percent). 1H NMR (200 MHz, CDCl3): δ 0.96 (3H, t, JHH = 7.3 Hz), 1.41 (2H, m), 1.89 (2H, m), 4.13 (3H, s), 4.34 (2H, t, JHH = 7.3 Hz), 7.47 (1H, t, JHH = 1.8 Hz), 7.62 (1H, t, JHH = 1.8 Hz),10.67 (1H,s). MS(ESI+) [m/z (rel. int. (percent))]: 139 (100, [BMIM]). MS(ESI) [m/z (rel. int. (percent))]: 210 (100, Cl[BMIM]Cl)
72% at 70℃; for 24 h; General procedure: C4mimBr was synthesized according to the reported literatures.1 In a 100 mL round-bottom flask, 1-methylimidazole (8.21 g, 0.1 mol) was mixed with n-butyl bromide (16.44 g, 0.12 mol) and allowed to reflux for 24 h at 70 °C. The excess n-butyl bromide was distilled off under reduced pressure and the residue was finally extracted thoroughly 2-3 times (50 mL each) with diethyl ether to remove the traces of unreacted starting materials. A white solid of 1-n-butyl-3-methylimidazolium bromide was obtained in 87percent yield.
72.4% at 75℃; for 48 h; Equipped with a blender,Reflux condenser and a thermometer 500mL three-necked flask was added 68.60g N-methyl imidazole and 85.65g chlorobutane,And were added 80mL cyclohexane and toluene as the reaction medium,Control the temperature inside the bottle is 70 ,After stirring for 48h, the upper solvent and the unreacted raw materials were removed by pouring,The lower oily liquid was hot with ethyl acetate 4 times (each time the amount of 20mL)Remove the liquid transfer to a single mouth flask,Rotate under reduced pressure (water bath temperature was controlled at 70 ) to remove part of the solvent and raw materials unreacted raw materials.Turn the steam transfer to the vacuum drying oven,The temperature is 70 ,Vacuum dried 36h,That is to obtain the intermediate l-butyl-3-methylimidazolium chloride [Bmim] Cl,Yield 68.6percent.
70.2% at 80℃; for 36 h; 500 mL equipped with a stirrer, reflux condenser and thermometerThree-necked flask was added 68.60gN-methylimidazole and85.65g chlorobutane, and were added 80mL cyclohexane and toluene as the reaction medium,Control the temperature inside the bottle is 80 ,After stirring for 36h, the upper solvent and the unreacted raw materials were removed by pouring,The lower oily liquid was hot with ethyl acetate 4 times (each time the amount of 20mL)Remove the liquid transfer to a single mouth flask,Rotate under reduced pressure (water bath temperature was controlled at 70 ) to remove part of the solvent and raw materials unreacted raw materials. Turn the steam transfer to a vacuum oven, the temperature is 70 ,Drying in vacuo for 36 h gave the intermediate productL-butyl-3-methylimidazolium chloride[Bmim] Cl, yield 70.2percent.
68.2% at 70℃; for 48 h; In the presence of a stirrer,Reflux condenser and a thermometer was charged 68.60 g of N-methylimidazole in a 500 mL three-necked flaskAnd 85.65 g of chlorobutane,And adding 80mL of cyclohexane and toluene as reaction intermediates,The temperature in the control bottle is 70 ° C,After stirring for 48 h, the upper layer solvent and the unreacted starting material were removed by the pouring method,The lower oily liquid was washed 4 times with ethyl acetate (20 mL each)Remove the liquid from the lower layer to the vial,Vacuum distillation (water bath temperature control at 70 ° C) to remove part of the solvent and raw materials in the unreacted raw materials.Steaming finished transferred to a vacuum oven,The temperature is 70 ° C, vacuum drying 36h,To give the intermediate 1-butyl-3-methylimidazolium chloride[Bmim] C1, yield 68.2percent.
61% at 65℃; for 11 h; 9.27g (0.1mol) 1-chlorobutane was added dropwise to 11.50g (0.14mol) 1-methylimidazole. The mixture was heated at 65°C under stirring for 11h. Phase separation occurred and the viscous yellow liquid obtained was washed with ethyl acetate (60 mL for three times). Then the product was filtered and dried in vacuum dryness case until constant weigh. 10.80g [bmim]Cl was obtained, and the yield of colorless liquid was 61percent.

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  • 2
  • [ 109-69-3 ]
  • [ 79917-90-1 ]
Reference: [1] Patent: US2003/50507, 2003, A1,
  • 3
  • [ 284049-75-8 ]
  • [ 79917-90-1 ]
YieldReaction ConditionsOperation in experiment
93.5% With hydrogenchloride In water at 50℃; Cooling Comparative examples C1 to C3198 g (1 mol) of BMIM OAc (1-butyl-3-methylimidazolium acetate) are placed in a round-bottom flask which has been made inert and is provided with a dropping funnel and reflux condenser. The amount of acid indicated in the appended table is added slowly while stirring, with the temperature being kept below 50° C. (an exothermic reaction is observed during the addition; the temperature is kept down either by appropriately slow addition with air cooling or by cooling with water).After cooling to room temperature, the major part of the volatile constituents is taken off at a pressure of 0.1 mbar, with the internal temperature being increased to 120° C. When no more low boilers are given off from the mixture under these conditions, the mixture is cooled and nitrogen is admitted. The residue is transferred to the reservoir of the short-path distillation and fed in at a rate of 100 ml/h at the evaporator temperature indicated below. The pressure in the short-path distillation is set to 0.05 mbar. The product is obtained as bottom output, so that the short-path distillation here functions as a very efficient form of low boiler stripping.The condensed low boilers comprise water (when an aqueous reagent is added) and acetic acid. BMIM Evaporator Product OAc:acid temp. (salt having Yield No. Acid mol:mol ° C. the new anion) percent Purity* C1 HCl; 35percent in water 1:1.033 170 BMIM Cl 93.5 comprises 20 mol percent of HOAc after first passage comprises 3 mol percent of HOAc after second passage C2 CF3COOH 1:1.017 150 BMIM TFA 90.9 comprises 13 mol percent of HOAc after first passage (trifluoroacetic acid) comprises 4 mol percent of HOAc after second passage C3 CH3SO3H 1:1.005 170/190 BMIM 92.3 comprises 9 mol percent of HOAc after first passage (methanesulfonic CH3SO3 no HOAc after the second passage acid) *Analysis by H-NMR
Reference: [1] Patent: US2010/217010, 2010, A1, . Location in patent: Page/Page column 7-8
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  • [ 4316-42-1 ]
  • [ 149-73-5 ]
  • [ 79917-90-1 ]
YieldReaction ConditionsOperation in experiment
50 %Spectr. at 0 - 110℃; for 24 h; General procedure: 1-butyl-imidazole and acid source were mixed at 0 °C, after removing the water under reduced pressure by using phosphorus pentoxide, after the addition of trimethyl ortho formate is reacted at a given temperature for a predetermined time to remove the triisopropyl ortho formate remaining in the reduced pressure the ionic liquid 13 to 22 respectively was produced.The yield of the ionic liquid 13 to 22 prepared each ion of the acid source, the reaction temperature and reaction time used in the production and accordingly liquids is shown in Table 1.
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[2] Patent: KR2015/79403, 2015, A, . Location in patent: Paragraph 0108-0112
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  • [ 497144-87-3 ]
  • [ 79917-90-1 ]
Reference: [1] Patent: WO2006/27070, 2006, A1, . Location in patent: Page/Page column 30
  • 6
  • [ 65039-05-6 ]
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YieldReaction ConditionsOperation in experiment
27% With lithium hexafluorophosphate In dichloromethane at 20℃; for 72 h; Inert atmosphere Lithium hexafluorophosphate was mixed with 1-butyl-3-methylimidazolium chloride, [Bmim][Cl] in a two-neck round bottom flask. The reaction mixture was stirred in dry dichloromethane at room temperature for 72 h under an inert atmosphere. The reaction mixture was filtered and the excess lithium chloride was washed with dichloromethane. The combined organic extraction was washed with distilled water until the aqueous layer was free from halide, determined using the silver nitrate test. The dichloromethane layer was concentrated to give a yellow liquid. The yellow liquid was treated with activated charcoal and filtered through acidic alumina to give 1-butyl-3-methylimidazolium hexafluorophosphate (27percent) as a colorless liquid 28. IR (KBr) 3392.27 (OH), 1649.54 (C=C), 1008.56 (CN) cm–1; 1H NMR (400 MHz, DMSO-d6) δ 9.00 (1H, s, CH-2), 7.67 (1H, s, CH-4), 7.61 (1H, s, CH-5), 4.14 (2H, t, J= 7.32 Hz, NCH2CH2CH2CH3), 3.83 (3H, s, NCH3), 1.76 (2H, m, NCH2CH2CH2CH3), 1.26 (2H, m, NCH2CH2CH2CH3), 0.89 (3H, t, J= 7.32 Hz, NCH2CH2CH2CH3); 13C NMR (100 MHz,DMSO-d6) 136.9 (NCN), 124.0 (C-4), 122.6 (C-5), 49.1 (NCH2CH2CH2CH3), 36.1 (NCH3), 31.8 (NCH2CH2CH2CH3), 19.2 (NCH2CH2CH2CH3), 13.5 (NCH2CH2CH2CH3); MS (ESI+) m/z 423.21 [2(C4C1im) + PF6] and 139.12, [C4C1im], MS (ESI-) m/z 429.05 [2(PF6) + (C4C1im)] and 144.96 [PF6].
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