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[ CAS No. 64697-40-1 ] {[proInfo.proName]}

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Chemical Structure| 64697-40-1
Chemical Structure| 64697-40-1
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Quality Control of [ 64697-40-1 ]

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Product Details of [ 64697-40-1 ]

CAS No. :64697-40-1 MDL No. :MFCD03095432
Formula : C12H23ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :OXFBEEDAZHXDHB-UHFFFAOYSA-M
M.W : 230.78 Pubchem ID :2734223
Synonyms :

Calculated chemistry of [ 64697-40-1 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.75
Num. rotatable bonds : 7
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 68.79
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) : -4.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : -2.86
Log Po/w (XLOGP3) : 4.3
Log Po/w (WLOGP) : -0.32
Log Po/w (MLOGP) : 2.47
Log Po/w (SILICOS-IT) : 2.37
Consensus Log Po/w : 1.19

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.76
Solubility : 0.0397 mg/ml ; 0.000172 mol/l
Class : Soluble
Log S (Ali) : -4.2
Solubility : 0.0146 mg/ml ; 0.0000633 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.2
Solubility : 0.146 mg/ml ; 0.000632 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.03

Safety of [ 64697-40-1 ]

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

Application In Synthesis of [ 64697-40-1 ]

* 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.

  • Downstream synthetic route of [ 64697-40-1 ]

[ 64697-40-1 ] Synthesis Path-Downstream   1~85

  • 2
  • [ 616-47-7 ]
  • [ 111-85-3 ]
  • [ 64697-40-1 ]
YieldReaction ConditionsOperation in experiment
72.4% In cyclohexane; toluene; at 75℃; for 48h; In the presence of a stirrer,The reflux condenser and the thermometer were charged with 82. lg in a 500 mL three-necked flaskN-methylimidazole and 163.5 g of 1-chlorooctane,And adding 80mL of cyclohexane and toluene as reaction intermediates,The temperature in the control bottle is 75 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,The solvent and the unreacted raw material in the raw material are removed by steam distillation under reduced pressure.The steam was transferred to a vacuum oven at a temperature of 70 C,Vacuum drying 36h,To give the intermediate product 1-octyl-3-methylimidazolium chloride[Omim] C1, yield 72.4%
72.4% In cyclohexane; toluene; at 75℃; for 48h; Equipped with a blender,A reflux condenser and a thermometer was charged with 82.1 g of N-methylimidazole and 163.5 g of 1-chlorooctane,And were added 80mL cyclohexane and toluene as the reaction medium,Control the temperature inside the bottle is 75 ,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,Under reduced pressure, the solvent was distilled off and the unreacted raw materials in the raw materials were removed by rotary evaporation under reduced pressure.Turn the steam transfer to the vacuum drying oven,The temperature is 70 ,Vacuum dried 36h,Ie to obtain the intermediate 1-octyl-3-methylimidazolium chloride [Omim] Cl,Yield 72.4%.
71% In ethyl acetate; for 72h;Inert atmosphere; Reflux; 1-Octyl-3-methylimidazolium chloride, [OMIM]Cl.; In a round-bottom flask equipped with a magnetic stirrer, a dry nitrogen inlet and a reflux condenser topped with a nitrogen bubbler, N-methylimidazole (20 cm3, 20.6 g, 0.251 mol), 1-chlorooctane (47 cm3, 41.1 g, 0.276 mol) and ethylacetate (50 cm3) were introduced. The homogeneous solution was heated under reflux for 3 days. The biphasic system obtained was separated and the lower viscous product phase was washed with ethylacetate (3×50 cm3). The product was dried in vacuo (0.1 mbar, 5 hours, 50 C.) to yield a pale yellow viscous oil (41.1 g, 71%).
at 80℃; for 48h; General procedure: lIn the present study, the preparation of MAILs (shown inScheme 2), such as C4mim/FeCl4, was synthesized according to the following methods (Bourissou, Guerret, Gabbai, & Bertrand,2000). Firstly, N-butylpyridiumchloride intermediates were pre-pared by reacting of 0.2 mol N-methylpyrrolidine with 0.24 mol n-chlorobutane at 80C for 48 h with magnetic stirring. The reaction intermediate products were purified and recrystallized from acetonitrile repeatedly, subsequently washed with ethyl acetate for four times and dried in a vacuum oven at 60 C for 24 h. Secondly, the intermediates Cnmim Cl were mixed with equimolar of FeCl3·6H2O under N2 atmosphere with magnetic stirring at room temperature (~25C). The final products were washed with ether and deionized water repeatedly, purified by reduced pressure distillation and dried in a vacuum oven at 60 C for 24 h successively. The MAILs, Cnmim/FeCl4, were obtained for further experiments.
at 80℃; for 72h;Inert atmosphere; Synthesis of 1-Methyl-3-octylimidazolium Chloride1-Methyl-3-octylimidazolium chloride (OMImCl) was synthesisedaccording to the following procedure. In a 250-mL roundbottomflask with a magnetic stirrer and a water-cooling system,1-methylimidazole (35.57 g, 0.433 mol) and 1-chlorooctane(70.86 g, 0.476 mol) were added. The mixture was stirred at808C for 72 h under a nitrogen atmosphere and subsequentlywashed three times with 80mL of ethyl acetate and dried under high vacuum for 4 h at 808C. Water was added to OMImCl forthe washing step to decrease the viscosity, thereby affordingmore efficient mixing.dH (CDCl3, 500 MHz) 10.17 (1H, s), 7.51 (1H, s), 7.27(1H, s), 3.97 (2H, t), 3.78 (3H, s), 1.56 (2H, m), 0.92(10H, m), 0.49 (3H, t).
at 80℃; for 24h;Inert atmosphere; General procedure: 1-butyl 3-methyl imidazolium chloride ([C4]Cl) was synthe-sized by stirring1:1 molar ratio of imidazolium and 1-butyl chlorideat 80C for 24 h in nitrogen atmosphere. After recrystallizationfrom ethyl acetate, the intermediate product was obtained. Then0.47 g of [C4]Cl and 2.88 g of PMoA were dissolved in deionizedwater, respectively, and mixed under constant stirring for 12 h.Then a white precipitate was formed. The product was filtered andwashed for several times with deionized water until chloride-free(AgNO3aqueous test). Finally, the obtained [C4]PMo (PIL4) wasdried overnight at 80C in oven. The preparation road of PIL4 isshown in Scheme 1, the other PILs are similar to PIL4. In addition,[C8]PMo, [C12]PMo, [C18]PMo are marked as PIL8, PIL12, PIL18,respectively. Their HNMR is shown in Fig. S4 and Table S4.3.
at 69.84℃; for 72h;Inert atmosphere; The syntheses of the ionic liquids were based on the metathesisreaction of sodium thiocyanate with 1-hexyl-3-methylimidazoliumchloride ([HMIM][Cl]) and 1-octyl-3-methylimidazolium chloride([OMIM][Cl]) [24].For the synthesis of the ionic liquids, 1-hexyl-3-methylimidazoliumchloride, [HMIM][Cl], and 1-octyl-3-methylimidazolium chloride,OMIM][Cl], two naked round-bottom flask containing 1-methylimidazole were put on a magnetic stirrer and excess amount of1-chlorohexane/1-chlorooctane was added to the flask dropwise fromthe dropper funnel in an ice bath. After completion of the haloalkaneaddition, the entire system has been refluxed for 72 h under argonatmosphere with gradually rising temperature up to 343 K [25]. Themajor impurities in the thiocyanate based IL was unreacted [HMIM][Cl]or [OMIM][Cl], NaCl and the excess NaSCN. The prepared ILwaswashedthen with the dry dichloromethane. The impure IL is solved in this solvent,but NaSCN and NaCl salts are not soluble and separate fromthe solution.The unreacted raw materials are evaporated under reducedpressure using a rotary evaporator. The remaining liquid is furtherdried at about T = 343 K under reduced pressure using high vacuumpump. Since ILs are very hygroscopic compounds, to remove traceamount of moisture, both of the obtained imidazolium based ionic liquidswere dried overnight at about T = 353 K under high vacuum(0.1 Pa) prior to use. Water contents of the prepared ionic liquidswere found by Karl Fischer method using a Karl Fischer titrator (751GPD Titrino-Metrohm, Herisau, Switzerland) which was less than0.1%. The [HMIM][SCN] and [OMIM][SCN] were analyzed by 1H NMR(Brucker Av-400) and FT-IR (Brucker, tensor27) to confirm the absenceof any major impurities (supplementary content). The physical propertiesof pure chemicals used in this work including experimental densities,speeds of sound, and refractive indices are given in Table 2 andcompared with those values reported in the literature.
In toluene; at 180℃; for 72h;Inert atmosphere; Cooling with ice; To a 100 ml round-bottom flask equipped with reflux condenser and magnetic stirring bar connected with a nitrogen cylinder, 10 ml (125 mmol) of 1-methyl imidazole and 12.6 ml toluene was added to an ice bath. After 5 min of stirring, 23.4 ml (138 mmol) 1-chloro octane was added. The solution was heated to reflux at 180C for 72 h, yielding a two-phase mixture of [OmimCl] and toluene. Then, the toluene was decanted and the product was recrystallized with acetone three times. The final product was then dried in a Schlenk line at 80C for 7 h before use. 1H NMR (CdCl3, 400 MHz), d (ppm): 0.69 (t), 1.00 (m), 1.70 (m), 3.98 (s), 4.17 (t), 4.68 (s), 5.27 (s), 7.38 (d), and 8.44 (d).
In acetonitrile; at 70℃; for 72h;Inert atmosphere; [C8mim]Cl was synthesized according to standard method[8] by reacting n-chlorooctane (6.5 g, 43.77 mmol) with nmethylimidazole (3.56 g, 43.35 mmol) in a round bottomflask in acetonitrile media followed by refluxing the solutionat 70 C for 72 h under N2 atmosphere. The final product was a light yellow colored viscous liquid, which was then cooled to room temperature and washed several times with ethyl acetate to remove unreacted startingmaterials. Excess ethyl acetate was decanted and theremaining solvent was removed by evaporation undervacuum and further dried in vacuum oven for 72 h to getthe final product. Water content obtained in the IL wasfound to be less than 290 ppm using Karl-Fischer titration analysis. The product was flushed with N2 gas and kept in adry place before using.
at 90℃; for 48h;Inert atmosphere; 1) Synthesis of 1-octyl-3-methylimidazole hydrochloride:The vacuum distillation of N-methylimidazole was carried out(4.1 g, 50 mmol) in a 100 mL reaction kettle,Additional 1-chlorooctane (8.2 g, 55 mmol) was added,After the reactor was evacuated, it was charged and discharged three times with nitrogen gas, The temperature was raised to 90 C under a nitrogen atmosphere,Reaction 48h.After the reaction, a light yellow oily substance was formed,After washing several times with ethyl acetate80oC vacuum drying can be1-octyl-3-methyl-imidazole hydrochloride.
at 69.99℃; for 48h; General procedure: [Bmim][FeCl4] was prepared via two steps [2]. Firstly, the intermediate 1-butyl-3-methylimidazoliumchloride ([Bmim]Cl) was synthesized by reacting 1-methylimidazole (0.20 mol) with 1-chlorobutane (0.24 mol) at 343.15 K for 48 h. The product was then washed with acetone for three times and dried in vacuum. Subsequently, the purified [Bmim]Cl was mixed with equimolar of FeCl3 under N2 atmosphere and stirred at room temperature for 12 h, leading to a dark brown liquid product. [Hmim][FeCl4] and [Omim][FeCl4] were prepared similarly, but 1-chlorobutane was replaced by 1-chlorohexane and 1-chlorooctane, respectively.
at 80℃;Inert atmosphere; General procedure: ILs containing chloride anion were synthesized by reacting 1-methylimidazole (0.1 mol) with excess amount of 1-cloroalkane (1-chlorooctane, 1-chlorodecane, 1-chlorododecane or 1-chlorotetradecane)(0.11 mol) without any additional solvent. At first the reaction mixturewas heated and continually stirred at 80 C for 72-120 h in a round bottomedflask, fitted with a reflux condenser, under N2 atmosphere. Thenitwas cooled to room temperature andwashed thrice with 50ml diethyl ether to remove excess starting material. Finally the resulting productswere dried under vacuum at 60 C for 48 h to remove all solvents [28].To prove the synthesis verification, ILs were tested with AgNO3 andwhite AgCl precipitation was seen, so no further purification was required.
at 70℃; Equal molar amounts of chlorooctane and 1-methylimidazole were added to a round bottom flask and stirred for 24-72h (until two phases formed) under reflux condition at 70C. The unreacted starting material which was in the upper phase was decanted and ethyl acetate was added and decanted again to remove the unreacted materials. The remained ethyl acetate was removed by heating the bottom phase under vacuum up to 70C [27].

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  • 3
  • [ 64697-40-1 ]
  • 1-octyl-3-methylimidazolium hexafluorophosphate [ No CAS ]
  • 4
  • [ 16156-52-8 ]
  • [ 64697-40-1 ]
  • 1-methyl-3-n-octylimidazolium methanesulfonate [ No CAS ]
  • [ 111-85-3 ]
  • 6
  • [ 2926-27-4 ]
  • [ 64697-40-1 ]
  • [ 403842-84-2 ]
  • 7
  • [ 1934-75-4 ]
  • [ 64697-40-1 ]
  • 1-octyl-3-methylimidazolium dicyanoamide [ No CAS ]
  • 8
  • [ 29420-49-3 ]
  • [ 64697-40-1 ]
  • 1-octyl-3-methylimidazolium nonafluorobutanesulfonate [ No CAS ]
  • 9
  • [ 64697-40-1 ]
  • [ 90076-67-8 ]
  • [ 178631-04-4 ]
  • 10
  • [ 7446-70-0 ]
  • [ 64697-40-1 ]
  • 1-n-octyl-3-methylimidazolium tetrachloroaluminate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Embodiment 4 Please refer to FIG. 5, which is a view showing a result of a fourth preferred embodiment. As shown in the figure, 1.051 g (0.00458 moles) of 1-octyl-3-methylimidazolium chloride (OMIC) and 0.916 g (0.00687 moles) of aluminum trichloride are used to prepare a set of chloroaluminate ionic liquid; and, 1.573 g (0.00458 moles) of 1-hexadecyl-3-methylimidazolium chloride (HDMIC) and 0.916 g (0.0687 moles) of aluminum trichloride are used to prepare the other set of chloroaluminate ionic liquid. Both of the flasks are processed through oil bath under 50 C. A 16 g of reaction feedstock is injected into each flask for an isomerization with a stirring speed of 400 rpm.After 6 hrs of reaction, a result of the chloroaluminate ionic liquid using OMIC shows a reaction conversion of endo-tetrahydrodicyclopentadiene 51 as 67% and a selectivity of exo-tetrahydrodicyclopentadiene 52 as 100%. A result of the other chloroaluminate ionic liquid using HDMIC shows a reaction conversion of endo-tetrahydrodicyclopentadiene 51 as 70% and a selectivity of exo-tetrahydrodicyclopentadiene 52 as 100%. Accordingly, a result of the chloroaluminate ionic liquid using BMIC having the same mole ratio (0.00458 moles in 0.0687 moles) shows a reaction conversion of endo-tetrahydrodicyclopentadiene 51 as 81% and a selectivity of exo-tetrahydrodicyclopentadiene 52 as 100%.
  • 11
  • [ 105473-46-9 ]
  • [ 64697-40-1 ]
  • C9H17NO5S(1-)*C12H23N2(1+) [ No CAS ]
  • 12
  • [ 64697-40-1 ]
  • 1-methyl-3-(n-octyl)imidazolium fluoride [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With silver fluoride; In water; at 25℃; for 0.5h; Into an Erlenmeyer flask, 5.0 g of 1-methyl-3-(n-octyl)imidazolium chloride and 50 g of water were charged and dissolved. After 2.74 g of silver(I) fluoride and 50 g of water were charged into another Erlenmeyer flask and dissolved, two aqueous solutions were mixed at 25C and the stirring was continued for 30 minutes at the same temperature. The crystalline precipitated after the reaction was filtered and washed with water. The filtrate and wash liquid obtained were joined and concentrated to obtain 5.8 g of the colorless oil. The obtained oil was identified as 1-methyl-3-(n-octyl)imidazolium fluoride trihydrate from the result of the elementary analysis. Yield: 100%. Elementary analytical value: C: 53.6, H: 10.8, N: 10.1, F: 6.7 Calculated value: C: 53.6, H: 11.0, N: 10.4, F: 7.1 1H-NMR (delta ppm, DMSO-d6, TMS standard): 0.86 (m, 3H), 1.20 (m, 10H), 1.77 (m, 2H), 3.89 (s, 3H), 4.16 (q, 2H), 7.80 (d, 2H), 10 (bs, 1H)
YieldReaction ConditionsOperation in experiment
Specific examples of these compounds include the following: ... 1-methyl-3-butyl imidazolium chloride, 1-methyl-3-butyl imidazolium bromide, 1-methyl-3-propyl imidazolium chloride, 1-methyl-3-hexyl imidazolium chloride, 1-methyl-3-octyl imidazolium chloride, 1-methyl-3-decyl imidazolium chloride, 1-methyl-3-dodecyl imidazolium chloride, 1-methyl-3-hexadecyl imidazolium chloride, ...
Specific examples of these compounds include the following: ... 1-methyl-3-dodecyl imidazolium chloride, 1-methyl-3-hexadecyl imidazolium chloride, 1-methyl-3-octadecyl imidazolium chloride, 1-methyl-3-hexyl-imidazolium chloride, 1-methyl-3-octyl-imidazolium chloride, 1-methyl-3-decyl-imidazolium chloride, 1-methyl-3-dodecyl-imidazolium chloride, 1-methyl-3-hexadecyl-imidazolium chloride, ...
A process according to claim 1 wherein hydrocarbyl substituted imidazolium or pyridinium halide is selected from the group consisting of: ... 1-methyl-3-dodecyl imidazolium chloride, 1-methyl-3-hexadecyl imidazolium chloride, 1-methyl-3-octadecyl imidazolium chloride, 1-methyl-3-hexyl-imidazolium chloride, 1-methyl-3-octyl-imidazolium chloride, 1-methyl-3-decyl-imidazolium chloride, 1-methyl-3-dodecyl-imidazolium chloride, 1-methyl-3-hexadecyl-imidazolium chloride, ...
A process according to claim 1 wherein hydrocarbyl substituted imidazolium or pyridinium halide is selected from the group consisting of: ... 1-methyl-3-butyl imidazolium chloride, 1-methyl-3-butyl imidazolium bromide, 1-methyl-3-propyl imidazolium chloride, 1-methyl-3-hexyl imidazolium chloride, 1-methyl-3-octyl imidazolium chloride, 1-methyl-3-decyl imidazolium chloride, 1-methyl-3-dodecyl imidazolium chloride, 1-methyl-3-hexadecyl imidazolium chloride, ...
, wherein said salt is selected from the group consisting of: 1-ethyl-3-methylimidazolium chloride, 1-ethyl-3-methylimidazolium bromide, 1-butyl-3-methylimidazolium chloride, 1-hexyl-3-methylimidazolium chloride, 1-methyl-3-octylimidazolium chloride, 1-decyl-3-methylimidazolium chloride, 1-decyl-3-methylimidazolium bromide, 1-dodecyl-3-methylimidazolium chloride, 1-methyl-3-tetradecylimidazolium chloride, ...

  • 14
  • indium(III) chloride [ No CAS ]
  • [ 64697-40-1 ]
  • 1-(n-octyl)-3-methylimidazolium tetrachloroindate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Heating / reflux; 2.3.6 i-Octyl-3-methylimidazolium chloroindate(lll) [C8mim][lnCI4]; lndium(lll)chloride (0.707 g, 3.2 mmol) was added to a round bottom flask containing 1-octyl-3-methylimidazolium chloride (0.733 g, 3.2 mmol). The mixture was heated with an oil bath until a homogeneous liquid was formed. The formed [C8mim][lnCI4] was dried under high vacuum. 1H-NMR (300 MHz, CDCI3, ppm): delta 0.87 (3H, t, J 7.0 Hz, CH3), 1.33 (10H, m, CH2), 1 ,91 (2H, m, J 7.5 Hz, NCH2CH2), 4,00 (3H, s, NCH3), 4.22 (2H, t, J 7.5 Hz, NCH2), 7,35 (1 H, d, J 1.8 Hz, C(5)H), 7,37 (1 H, d, J 1.8 Hz, C(4)H), 8,57 (1 H, s, C(2)H. 13C-NMR (300 MHz, CDCI3, ppm): delta 14.06 (CH3), 22.50 (CH2), 26.15 (CH2), 28.77 (CH2), 28.88 (CH2), 29.99 (CH2), 31.57 (CH2), 37.03 (NCH3), 50.55 (NCH2), 122.58 (C(5)H), 123.96 (C(4)H), 134.86 (C(2)H). Elemental analysis: Calculated: C: 32.15 H: 5.08 N: 6.1 Cl: 31.98 In: 26.85 Found: C: 31.89 H: 5.13 N: 6.20 Cl: 31.38 In: 25.40.
  • 15
  • [ 50-00-0 ]
  • [ 64697-40-1 ]
  • [ 1122494-14-7 ]
  • 16
  • Cs[closo-1-HCB11H5Cl6] [ No CAS ]
  • [ 64697-40-1 ]
  • 1-octyl-3-methylimidazolium 7,8,9,10,11,12-hexachlorocarborane [ No CAS ]
  • 17
  • cesium monocarba-closo-dodecaborate [ No CAS ]
  • [ 64697-40-1 ]
  • 1-octyl-3-methylimidazolium carborane [ No CAS ]
  • 18
  • [ 94-74-6 ]
  • [ 64697-40-1 ]
  • [ 1082249-19-1 ]
YieldReaction ConditionsOperation in experiment
99% In water; for 24h; Example VI. Synthesis of l-methyl-3-octyl-imidazolium (4-chloro-2- methylphenoxy)acetate0.005 Mole of (4-chloro-2-methylphenoxy)acetic acid were and 40 cm of distilled water were placed in a 100 cm3 round bottom flask equipped with magnetic stirrer. The mixture was heated at 323 K for 40 minutes. Then the stoichiometric amount of 1- methyl-3-octyl-imidazolium chloride in 10 cm3 of water was added and mixture was vigorously stirred for 24 hours, water was evaporated and 30 cm3 of acetone was added to the residue. The precipitate was filtered off and the acetone was evaporated on rotary <n="9"/>evaporator. The product was dried at 323K under reduced pressure. The resulting liquid product is well soluble in water. The yield was 99%.The structure of synthesized salt was confirmed ba elemental analysis for CHN. For the compound of the general formula C2IH31ClN2O3 (M = 394.94) the calculated results were: C = 63.86%, H = 7.91%, N = 7.09% while those found were: C = 64.14%, H = 8.08%, N = 7.43%.
  • 19
  • [ 63748-65-2 ]
  • [ 64697-40-1 ]
  • 1-octyl-3-methylimidazolium dodecahydrodicarba-nido-undecaborate [ No CAS ]
  • 20
  • [ 329065-91-0 ]
  • [ 64697-40-1 ]
  • [C8mim+][C6F13BF3-] [ No CAS ]
  • 21
  • [ 64697-40-1 ]
  • potassium trifluoro(1,1,2,2,2-pentafluoroethyl)borate [ No CAS ]
  • [ 1141799-17-8 ]
  • 22
  • [ 64697-40-1 ]
  • [ 329065-90-9 ]
  • [C8mim+][C3F7BF3-] [ No CAS ]
  • 23
  • [ 64697-40-1 ]
  • [ 476639-91-5 ]
  • [C8mim+][C4F9BF3-] [ No CAS ]
  • 24
  • 2NH4(1+)*[B10Cl10](2-)=[NH4]2[B10Cl10] [ No CAS ]
  • [ 64697-40-1 ]
  • [1-octyl-3-methylimidazolium]2[B10Cl10] [ No CAS ]
  • 25
  • 2NH4(1+)*[B12Cl12](2-)=[NH4]2[B12Cl12] [ No CAS ]
  • [ 64697-40-1 ]
  • [1-octyl-3-methylimidazolium]2[B12Cl12] [ No CAS ]
  • 26
  • (CH3)3NH(1+)-nido-7.8-B9C2H12(1-) [ No CAS ]
  • [ 64697-40-1 ]
  • [1-octyl-3-methylimidazolium][nido-C2B9H12] [ No CAS ]
  • 27
  • caesium cobalt(III)bis(1,2-dicarboilide) [ No CAS ]
  • [ 64697-40-1 ]
  • [1-octyl-3-methylimidazolium][commo-3,3'-Co(1,2-C2B9H11)2] [ No CAS ]
  • 28
  • hydroxygallium naphthalocyaninetetrasulfonic acid [ No CAS ]
  • [ 64697-40-1 ]
  • 4C12H23N2(1+)*C48H21GaN8O13S4(4-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% In methanol; water; Example 2; Tetra(1-methyl-3-octylimidazolium) salt; To a solution of hydroxygallium(III) naphthalocyaninetetrasulfonic acid (2.33 g, 2.08 mmol) in water (20 mL) and methanol (100 mL) was added a solution of 1-methyl-3-octylimidazolium chloride (1.90 mL, 1.92 g, 8.32 mmol) in methanol (20 mL). The reaction mixture was evaporated to half volume with heating under a stream of nitrogen and diluted with water (100 mL). The solid was filtered off and washed with hot water (3×250 mL) and hot acetone/water (50:50, 3×200 mL) and allowed to dry. The solid was then washed with ether (250 mL) and boiling hexane (250 mL) and dried to give the product as a dark-green powder (3.10 g, 79%).1H NMR (d6-DMSO) 0.87 (12H, t, J=6.3 Hz); 1.23 (40H, m); 1.77 (8H, m); 3.86 (12H, s); 4.14 (8H, t, J=7.2 Hz); 7.69 (4H, s); 7.75 (4H, s); 9.14 (4H, s); 7.9-11.2 (20H, m).
  • 29
  • [ 638-38-0 ]
  • [ 64697-40-1 ]
  • [ 1196891-27-6 ]
YieldReaction ConditionsOperation in experiment
With potassium tert-butylate; In tetrahydrofuran; at 20℃; for 15h; In a 200 ml round-bottom flask equipped with a magnetic stirrer was charged with l-methyl-3-octylimidazolium chloride (4.252 g, 18.4 mmol), manganese(II) acetate, (1.063 g. 6.14 mmol), and 80 niL of tetrahydrofuran. Potassium tert-butoxide (2.067 g, 18.4 mmol) was slowly added to the mixture, and the solution stirred for 15 hours at room temperature. After filtration, solvent and organic volatiles were removed in vacuo, affording a viscous orange oil.
  • 30
  • [ 64697-40-1 ]
  • [ 379712-23-9 ]
  • 31
  • [ 2966-50-9 ]
  • [ 64697-40-1 ]
  • 1-octyl-3-methylimidazolium trifluoroacetate [ No CAS ]
  • 32
  • [ 64697-40-1 ]
  • [ 1224877-70-6 ]
  • 33
  • ammonium 1,1,1,5,5,5-hexafluoro-2,4-pentanedionate [ No CAS ]
  • [ 64697-40-1 ]
  • 1-methyl-3-octylimidazolium 1,1,1,5,5,5-hexafluoro-2,4-pentanedionate [ No CAS ]
  • 34
  • [ 64697-40-1 ]
  • [ 497258-85-2 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; In water; 1-Octyl-3-Methylimidazolium hydrogensulfate ([OMIm][HSO4])[OMIm][HSO4] was prepared from the anion exchange of [OMIm][Cl] with H2SO4 in deionized water. The ionic liquid is then dried under vacuum. 1H NMR chemical shifts (relative to TMS internal standard) and coupling constants J/Hz: delta=8.65 (s, 1H), 7.39 (d, 2H, J=4.19), 4.17 (q, 2H, J=7.4), 3.93 (s, 3H), 1.87 (m, 4H), 1.32 (m, 6H) 0.87 (t, 3H, J=6.53); water content is less than 100 ppm.
  • 35
  • [ 64697-40-1 ]
  • C12H23N2(1+)*F3H2(1-) [ No CAS ]
  • 36
  • nickel(II) chloride hexahydrate [ No CAS ]
  • [ 64697-40-1 ]
  • bis(1-octyl-3-methylimidazolium) tetrachloronickelate [ No CAS ]
  • 37
  • [ 64697-40-1 ]
  • 1-octyl-3-methyl-3H-imidazolium nitrate [ No CAS ]
  • 38
  • silver nitrate [ No CAS ]
  • [ 64697-40-1 ]
  • silver(I) chloride [ No CAS ]
  • 39
  • [ 64697-40-1 ]
  • 1-octly-3-methylimidazolium persulfate [ No CAS ]
  • 40
  • [ 31121-93-4 ]
  • [ 64697-40-1 ]
  • [ 1335287-79-0 ]
YieldReaction ConditionsOperation in experiment
In ethanol; General procedure: The two new API-ILs, 1-octyl-3-methylimidazolium salicylate,[OMIm][Sal] and 1-octyl-3-methylimidazolium ibuprofenate, [OMIm][Ibu] (see the structure of API-IL in Fig. 1) were prepared from the1-octyl-3-methylimidazolium chloride [OMIm][Cl] and sodiumsalicylateand sodium ibuprofenate, respectively. 1-octyl-3-methylimidazoliumchloride was synthesized and purified according to the standardmethods reported in the references [24-27]. The water content of preparedionic liquid, [OMIm][Cl] determined by Karl Fischer method wasb0.05% in mass fraction. Characterization of the ionic liquid by 1HNMRspectroscopy showed good agreement as compared with the literatureand confirmed the absence of any significant impurity [26]. The purityof prepared ionic liquid was 98% in mass fraction. To synthesize the1-octyl-3-methylimidazolium salicylate ionic liquid [OMIm][Sal],(0.4 mol) sodium salicylate was dissolved in dried acetonitrile andadded slowly to (0.4 mol) [OMIm][Cl] dissolved in a minimum amountof dried acetonitrile. The resulting mixture was stirred overnigth atroomtemperature then the rotary evaporator at 350 K and then reducedpressurewas used to extract thewater in themixture. The resultingmixturewas subsequently dissolved in a large amount of dichloromethaneto observe white precipitate containing sodium chloride. The white precipitatewas then filtered and this process was continued until no whitesolid observed with the addition of dichloromethane [23-25]. The silvertest confirmed the lack of sodium chloride. The obtained product (a yellowishsolid) was further evaporated at 343.15 K by rotary evaporator[26]. The procedure for synthesis of 1-octyl-3-methylimidazoliumibuprofenate, [OMIm][Ibu] is similar to [OMIm][Sal] and the only differenceis applying the ethanol as solvent and heating at 353.15 K for 3 h at the beginning of the reaction. The water content of the [OMIm][Sal]and [OMIm][Ibu] determined using coulometric Karl Fischer titrator(Metrohm 756 KF) was approximately 0.1% in mass fraction. The 1HNMR (Brucker Av-400) spectroscopy was applied to characterize theprepared API-ILs (see Figs. S1 and S2).
  • 41
  • bismuth (III) nitrate pentahydrate [ No CAS ]
  • [ 64697-40-1 ]
  • bismuth (III) oxychloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethylene glycol; at 140℃; for 24h;Autoclave; General procedure: In a typical procedure, 0.001mol of Bi(NO3)3.5H2O was dissolved into an EG solution containing a stoichiometric amount of ionicl iquid[C16mim]Cl. The mixture was stirred for 30min,and thentransferred into 25mL Teflon-lined autoclave upto 80% of the total volume.The autoclave was then heated at 140 1C for 24h and cooled down to room temperature.The final product was separated by centrifugation,washed with distilled water and absolute ethanol four times,and dried under vacuumat50 1C for24h before further characterization. The other two kinds of BiOCl microspheres were obtained when [C16mim]Cl was changed into [Omim]Cl and [Bmim]Cl under the same experimental conditions. For the purpose of comparison,BiOCl samples were also prepared through the conventional method by using NaCl as the Cl sources.
  • 42
  • tin(ll) chloride [ No CAS ]
  • [ 64697-40-1 ]
  • [ 1381845-79-9 ]
  • [ 1381845-80-2 ]
  • 43
  • [ 64697-40-1 ]
  • 1-n-octyl-3-methylimidazolium iodide [ No CAS ]
  • 44
  • [ 3375-31-3 ]
  • [ 64697-40-1 ]
  • Pd(1-methyl-3-octylimidazol-2-ylidene)<SUB>2</SUB>Br<SUB>2</SUB> [ No CAS ]
  • 45
  • copper(II) choride dihydrate [ No CAS ]
  • [ 64697-40-1 ]
  • 2C12H23N2(1+)*Cl4Cu(2-) [ No CAS ]
  • 46
  • [ 616-47-7 ]
  • [ 544-10-5 ]
  • [ 64697-40-1 ]
  • 47
  • iron(III) chloride [ No CAS ]
  • [ 64697-40-1 ]
  • 0.5C12H23N2(1+)*0.5Cl(1-)*Cl1.5Fe0.5(1.5+) [ No CAS ]
  • 48
  • [ 7646-85-7 ]
  • [ 64697-40-1 ]
  • 0.5C12H23N2(1+)*0.5Cl(1-)*0.5Cl2Zn(2+) [ No CAS ]
  • 49
  • [ 7646-85-7 ]
  • [ 64697-40-1 ]
  • 0.4C12H23N2(1+)*0.4Cl(1-)*Cl1.2Zn0.6(1.2+) [ No CAS ]
  • 50
  • [ 7646-85-7 ]
  • [ 64697-40-1 ]
  • 0.75C12H23N2(1+)*0.75Cl(1-)*Cl0.5Zn0.25(0.5+) [ No CAS ]
  • 51
  • [ 7646-85-7 ]
  • [ 64697-40-1 ]
  • 0.67C12H23N2(1+)*0.67Cl(1-)*Cl0.66Zn0.33(0.66+) [ No CAS ]
  • 52
  • [ 7646-79-9 ]
  • [ 64697-40-1 ]
  • 0.67C12H23N2(1+)*0.67Cl(1-)*Cl0.66Co0.33(0.66+) [ No CAS ]
  • 53
  • nickel dichloride [ No CAS ]
  • [ 64697-40-1 ]
  • 0.67C12H23N2(1+)*0.67Cl(1-)*Cl0.66Ni0.33(0.66+) [ No CAS ]
  • 54
  • iron(II) chloride [ No CAS ]
  • [ 64697-40-1 ]
  • 0.67C12H23N2(1+)*0.67Cl(1-)*Cl0.66Fe0.33(0.66+) [ No CAS ]
  • 55
  • [ 1493-13-6 ]
  • [ 64697-40-1 ]
  • [ 403842-84-2 ]
  • 56
  • iron(III) chloride [ No CAS ]
  • [ 64697-40-1 ]
  • Cl(1-)*C12H23N2(1+)*2FeCl3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 20℃; for 0.5h; General procedure: ILs [Omim]ClxFeCl3 were prepared by reacting [Omim]Cl (0.1 mol) with anhydrous FeCl3 (x mol, x = 0.5, 1, 1.5, 2) with stirring for 30 min at room temperature. When x = 1.5 and 2, the IL is a reddish brown liquid. ILs [Omim]Clx2CuCl2, [Omim]Clx2BiCl3, [Omim]Clx2CoCl2, [Omim]Clx2MnCl2, [Omim]Clx2ZnCl2 and [Omim]Clx2NiCl2 were synthesized by the same method.
  • 57
  • copper dichloride [ No CAS ]
  • [ 64697-40-1 ]
  • Cl(1-)*C12H23N2(1+)*2CuCl2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 20℃; for 0.5h; General procedure: ILs [Omim]ClxFeCl3 were prepared by reacting [Omim]Cl (0.1 mol) with anhydrous FeCl3 (x mol, x = 0.5, 1, 1.5, 2) with stirring for 30 min at room temperature. When x = 1.5 and 2, the IL is a reddish brown liquid. ILs [Omim]Clx2CuCl2, [Omim]Clx2BiCl3, [Omim]Clx2CoCl2, [Omim]Clx2MnCl2, [Omim]Clx2ZnCl2 and [Omim]Clx2NiCl2 were synthesized by the same method.
  • 58
  • bismuth(III) chloride [ No CAS ]
  • [ 64697-40-1 ]
  • Cl(1-)*C12H23N2(1+)*2BiCl3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 20℃; for 0.5h; General procedure: ILs [Omim]ClxFeCl3 were prepared by reacting [Omim]Cl (0.1 mol) with anhydrous FeCl3 (x mol, x = 0.5, 1, 1.5, 2) with stirring for 30 min at room temperature. When x = 1.5 and 2, the IL is a reddish brown liquid. ILs [Omim]Clx2CuCl2, [Omim]Clx2BiCl3, [Omim]Clx2CoCl2, [Omim]Clx2MnCl2, [Omim]Clx2ZnCl2 and [Omim]Clx2NiCl2 were synthesized by the same method.
  • 59
  • [ 7646-79-9 ]
  • [ 64697-40-1 ]
  • Cl(1-)*C12H23N2(1+)*2CoCl2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 20℃; for 0.5h; General procedure: ILs [Omim]ClxFeCl3 were prepared by reacting [Omim]Cl (0.1 mol) with anhydrous FeCl3 (x mol, x = 0.5, 1, 1.5, 2) with stirring for 30 min at room temperature. When x = 1.5 and 2, the IL is a reddish brown liquid. ILs [Omim]Clx2CuCl2, [Omim]Clx2BiCl3, [Omim]Clx2CoCl2, [Omim]Clx2MnCl2, [Omim]Clx2ZnCl2 and [Omim]Clx2NiCl2 were synthesized by the same method.
  • 60
  • manganese(ll) chloride [ No CAS ]
  • [ 64697-40-1 ]
  • Cl(1-)*C12H23N2(1+)*2MnCl2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 20℃; for 0.5h; General procedure: ILs [Omim]ClxFeCl3 were prepared by reacting [Omim]Cl (0.1 mol) with anhydrous FeCl3 (x mol, x = 0.5, 1, 1.5, 2) with stirring for 30 min at room temperature. When x = 1.5 and 2, the IL is a reddish brown liquid. ILs [Omim]Clx2CuCl2, [Omim]Clx2BiCl3, [Omim]Clx2CoCl2, [Omim]Clx2MnCl2, [Omim]Clx2ZnCl2 and [Omim]Clx2NiCl2 were synthesized by the same method.
  • 61
  • [ 7646-85-7 ]
  • [ 64697-40-1 ]
  • Cl(1-)*C12H23N2(1+)*2ZnCl2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 20℃; for 0.5h; General procedure: ILs [Omim]ClxFeCl3 were prepared by reacting [Omim]Cl (0.1 mol) with anhydrous FeCl3 (x mol, x = 0.5, 1, 1.5, 2) with stirring for 30 min at room temperature. When x = 1.5 and 2, the IL is a reddish brown liquid. ILs [Omim]Clx2CuCl2, [Omim]Clx2BiCl3, [Omim]Clx2CoCl2, [Omim]Clx2MnCl2, [Omim]Clx2ZnCl2 and [Omim]Clx2NiCl2 were synthesized by the same method.
  • 62
  • nickel dichloride [ No CAS ]
  • [ 64697-40-1 ]
  • Cl(1-)*C12H23N2(1+)*2NiCl2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 20℃; for 0.5h; General procedure: ILs [Omim]ClxFeCl3 were prepared by reacting [Omim]Cl (0.1 mol) with anhydrous FeCl3 (x mol, x = 0.5, 1, 1.5, 2) with stirring for 30 min at room temperature. When x = 1.5 and 2, the IL is a reddish brown liquid. ILs [Omim]Clx2CuCl2, [Omim]Clx2BiCl3, [Omim]Clx2CoCl2, [Omim]Clx2MnCl2, [Omim]Clx2ZnCl2 and [Omim]Clx2NiCl2 were synthesized by the same method.
  • 63
  • sodium tetrakis(2-cyanoethoxy)borate [ No CAS ]
  • [ 64697-40-1 ]
  • 1-octyl-3-methylimidazolium tetrakis(2-cyanoethoxy)borate [ No CAS ]
  • 64
  • [ 36603-80-2 ]
  • [ 64697-40-1 ]
  • [ 1203710-60-4 ]
  • 65
  • iron(III) chloride [ No CAS ]
  • [ 64697-40-1 ]
  • [ 887305-68-2 ]
YieldReaction ConditionsOperation in experiment
at 20℃; General procedure: All the [FeCl4]-based ILs were synthesized according tothe procedures described in the literatures [27,28]. TheseILs are readily obtained by mixing equal molar iron trihalidewith corresponding cationic chloride ILs [29]. The mixtureswere stirred at room temperature, and a two-phasemixture consisting of a brown liquid and a water layer wasformed after a few minutes. The crude product was obtainedafter removal of the top water layer, and was then washedwith an excess of deionized water to remove un-reactedFeCl3 from the final product. Thus obtained magnetic ILswere dried under vacuum at 70 C for 48 h.
at 20℃; for 12h;Inert atmosphere; General procedure: [Bmim][FeCl4] was prepared via two steps [2]. Firstly, the intermediate 1-butyl-3-methylimidazoliumchloride ([Bmim]Cl) was synthesized by reacting 1-methylimidazole (0.20 mol) with 1-chlorobutane (0.24 mol) at 343.15 K for 48 h. The product was then washed with acetone for three times and dried in vacuum. Subsequently, the purified [Bmim]Cl was mixed with equimolar of FeCl3 under N2 atmosphere and stirred at room temperature for 12 h, leading to a dark brown liquid product. [Hmim][FeCl4] and [Omim][FeCl4] were prepared similarly, but 1-chlorobutane was replaced by 1-chlorohexane and 1-chlorooctane, respectively.
  • 66
  • [ 64697-40-1 ]
  • lithium bis((pentafluoroethyl)sulfonyl)amide [ No CAS ]
  • 1-methyl-3-octylimidazolium bis(pentafluoroethanesulfonyl)amide [ No CAS ]
  • 67
  • iron(III) chloride hexahydrate [ No CAS ]
  • [ 64697-40-1 ]
  • [ 887305-68-2 ]
YieldReaction ConditionsOperation in experiment
at 25℃;Inert atmosphere; General procedure: lIn the present study, the preparation of MAILs (shown inScheme 2), such as C4mim/FeCl4, was synthesized according to the following methods (Bourissou, Guerret, Gabbai, & Bertrand,2000). Firstly, N-butylpyridiumchloride intermediates were pre-pared by reacting of 0.2 mol N-methylpyrrolidine with 0.24 mol n-chlorobutane at 80C for 48 h with magnetic stirring. The reaction intermediate products were purified and recrystallized from acetonitrile repeatedly, subsequently washed with ethyl acetate for four times and dried in a vacuum oven at 60 C for 24 h. Secondly, the intermediates Cnmim Cl were mixed with equimolar of FeCl3·6H2O under N2 atmosphere with magnetic stirring at room temperature (~25C). The final products were washed with ether and deionized water repeatedly, purified by reduced pressure distillation and dried in a vacuum oven at 60 C for 24 h successively. The MAILs, Cnmim/FeCl4, were obtained for further experiments.
In ethanol; for 24h;Heating; General procedure: Firstly, 1-butyl-3-methylimidazolium chloride ([Bmim]Cl,0.1 mol) was added in an ethanol solution of iron chloride(0.1 mol) (Warnke et al. 2010). The mixture was stirred at 40 C for 24 h in the oil bath and a yellow solution was obtained. Then, the solvent (ethanol) in the solution was evaporated. Finally, the residue was washed with ethanoland dried in vacuum at 80 C for 24 h. Thus, the [Bmim]FeCl4 catalyst was prepared. According to the samemethod, [Cxmim]FeCl4 (x = 8, 12, 16) catalysts were prepared by replacing [Bmim]Cl with [Cxmim]Cl (x = 8, 12, 16), respectively. [Bmim]FeCl4, [Omim]FeCl4 and[C12mim]FeCl4 existed as liquids, whereas [C16mim]FeCl4 existed as solid at room temperature.
  • 68
  • copper dichloride [ No CAS ]
  • [ 64697-40-1 ]
  • 1-octyl-3-methylimidazolium copper trichloride [ No CAS ]
  • 69
  • bismuth (III) nitrate pentahydrate [ No CAS ]
  • [ 64697-40-1 ]
  • Bi(1+)*OCl(1-) = BiOCl [ No CAS ]
  • 70
  • [ 134-23-6 ]
  • [ 64697-40-1 ]
  • 1-octyl-3-methylimidazolium thiosalicylate [ No CAS ]
  • 71
  • sodium-bis(η2-1,1,2,2-tetracyano-ethylene-glycolato)borate [ No CAS ]
  • [ 64697-40-1 ]
  • 1-octyl-3-methylimidazolium-di(η2-1,1,2,2-tetracyano-ethyl-1,2-dioxy)borate [ No CAS ]
  • 72
  • [ 1620141-28-7 ]
  • [ 64697-40-1 ]
  • [ 1620141-12-9 ]
  • 73
  • [ 1620141-29-8 ]
  • [ 64697-40-1 ]
  • [ 1620141-13-0 ]
  • 74
  • [ 1620141-30-1 ]
  • [ 64697-40-1 ]
  • [ 1620141-14-1 ]
  • 75
  • [ 1620141-31-2 ]
  • [ 64697-40-1 ]
  • [ 1620141-15-2 ]
  • 76
  • [ 1620141-32-3 ]
  • [ 64697-40-1 ]
  • [ 1620141-16-3 ]
  • 77
  • [ 1620141-33-4 ]
  • [ 64697-40-1 ]
  • [ 1620141-17-4 ]
  • 78
  • [ 1620141-34-5 ]
  • [ 64697-40-1 ]
  • [ 1620141-18-5 ]
  • 79
  • [ 153448-18-1 ]
  • [ 64697-40-1 ]
  • [ 1620141-02-7 ]
  • 80
  • [ 50847-09-1 ]
  • [ 64697-40-1 ]
  • [ 1620141-03-8 ]
  • 81
  • [ 64697-40-1 ]
  • [ 51850-82-9 ]
  • [ 1620141-04-9 ]
  • 82
  • 2-vinyl-4,5-dicyanoimidazole [ No CAS ]
  • [ 64697-40-1 ]
  • [ 1620141-05-0 ]
  • 83
  • [ 64697-40-1 ]
  • [ 40953-34-2 ]
  • [ 1620141-06-1 ]
  • 84
  • [ 1122-28-7 ]
  • [ 64697-40-1 ]
  • C5HN4(1-)*C12H23N2(1+) [ No CAS ]
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