174899-82-2|1-Ethyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide| Ambeed

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

Structure of 174899-82-2

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size

Price

VIP Price

DE Stock

US Stock

Asia Stock

Global Stock

In Stock

{[ item.pr_size ]}

Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

Quality Control of [ 174899-82-2 ] Purity: 98% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Citations

High Efficiency n‐Type Doping of Organic Semiconductors by Cation Exchange

Zhao, Xiaolei ; Alsufyani, Maryam ; Tian, Junfu ; Lin, Yuanbao ; Jeong, Sang Young ; Han, Young Woo , et al.

DOI: 10.1002/adma.202412811 PubMed ID: 39385648 Adv. Mater.,2024,2412811.

Abstract: Achieving efficient doping in n-type conjugated polymers is crucial for their application in electronic devices. In this study, an n-type doping method is developed based on cation exchange that maintains a high doping level while ensuring a high degree of structural order, leading to significantly improved electrical conductivity. By investigating various dopants and ionic liquids, it is discovered that the choice of dopant influences doping efficiency, while the selection of ionic liquid affects cation exchange efficiency. Through careful selection of suitable dopants and ionic liquids, High doping levels are achieved remarkably in a short period, resulting in the highest conductivity (nearly 1 × 10⁻² S cm⁻¹) compared to other doping methods for poly{[N,N′-bis(2-octyldodecyl)-naphthalene-1,4,5,8-bis(dicarboximide)-2,6-diyl]-alt-5,5′-(2,2′-bithiophene)} (N2200). The findings highlight the robustness and efficiency of cation exchange doping as an effective approach for achieving high-quality n-type doping in conjugated polymers, thereby opening new avenues for the development of advanced polymer-based electronic devices.

Keywords: cation exchange ; conjugated polymer ; electrical conductivity ; n-type doping

Purchased from AmBeed: 174501-65-6 ; 174899-83-3 ; 143314-16-3 ; 174899-82-2

Product Details of [ 174899-82-2 ]

CAS No. :	174899-82-2
Formula :	C₈H₁₁F₆N₃O₄S₂
M.W :	391.31
SMILES Code :	CN1C=C[N+](CC)=C1.O=S([N-]S(=O)(C(F)(F)F)=O)(C(F)(F)F)=O
MDL No. :	MFCD03788927
InChI Key :	LRESCJAINPKJTO-UHFFFAOYSA-N
Pubchem ID :	11731903

Safety of [ 174899-82-2 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301+H311-H314-H401
Precautionary Statements:	P260-P264-P270-P273-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P405-P501
Class:	8(6.1)
UN#:	2922
Packing Group:	Ⅲ

Computational Chemistry of [ 174899-82-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	23
Num. arom. heavy atoms	5
Fraction Csp3	0.62
Num. rotatable bonds	5
Num. H-bond acceptors	11.0
Num. H-bond donors	0.0
Molar Refractivity	67.49
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	93.85 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.0
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.76
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	6.07
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.24
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.26
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.67

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.21
Solubility	0.244 mg/ml ; 0.000623 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.35
Solubility	0.175 mg/ml ; 0.000448 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.71
Solubility	77.0 mg/ml ; 0.197 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	Low
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-7.44 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	1.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.45

Application In Synthesis of [ 174899-82-2 ]

* 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 [ 174899-82-2 ]

[ 174899-82-2 ] Synthesis Path-Downstream 1~54

1
[ 7098-07-9 ]
[ 537031-78-0 ]
[ 174899-82-2 ]

References: [1]Chemical Communications,2003,p. 2334 - 2335.

2
[ 65039-08-9 ]
[ 90076-65-6 ]
[ 174899-82-2 ]

Yield	Reaction Conditions	Operation in experiment
87.1%	In water; at 60℃; for 2h;	2. Put 200g lithium bistrifluoromethylsulfonimide, 152g 1-ethyl-3-methylimidazole bromide salt and 400g pure water into the reactor,Warm to 60 , react for 2h,After standing for a while, 283 g of crude 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide salt was obtained. 3. Wash three times with pure water to obtain 251g of pure 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide salt.Distill it on a rotary evaporator under reduced pressure for 2h,Keep the temperature at 80 , remove most of the water,Finally, it is dried in a vacuum oven at 110 C for 12h.237 g of 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide was obtained. The purity of the product detected by liquid chromatography was 99.23%, and the yield was 87.1%;Ion chromatography detection: halogen ion 450ppm;ICP detection: Fe ion <1ppm, Pb ion <1ppm.
86%	In water; at 20℃; for 2h;Heating / reflux;	9.40 g of methylimidazole (0.115 mol) in 50 ml of ethyl acetate is introduced into a 500 ml three-necked flask equipped with a condenser. 14.25 g of ethyl bromide (0.126 mol) is added dropwise at ambient temperature. Then, the mixture is left for two hours under reflux before being extracted by three times 25 ml of ethyl acetate. The product is dried under vacuum at 70 C. for thirty minutes; this is ethylmethylimidazolium bromide. NMR 1H: (200 MHz, CD3CN): delta 9.42 (t, 1H, Ha); 7.63 (d, 1H, Hb); 7.55 (d, 1H, Hc); 3.93 (s, 3H, Hd); 4.28 (q, 2H, He); 1.50 (t, 3H, Hf) This product is added dropwise at ambient temperature to a mixture containing 50 ml of water and 31.37 g of lithium bis(trifluorosulphonyl)imide (0.109 mol). Then the mixture is stirred for two hours under reflux. The product is then extracted with three times 20 ml of dichloromethane before being evaporated under vacuum at 70 C. for 30 minutes. The overall yield is 86%. NMR 1H: (200 MHz, CD3CN): delta 8.46 (s, 1H, Ha); 7.42 (s, 1H, Hb); 7.37 (s, 1H, Hc); 3.93 (s, 3H, Hd); 4.28 (q, 2H, He); 1.50 (t, 3H, Hf)
	In water; at 70℃; for 24h;pH 6.0;	General procedure: The respective halide IL was dissolved in deionized water (pH =6) and after an equimolar amount of LiNTf2 in water had been added dropwise, the reaction mixture was stirred for 1 day at 70 C. Then CH2Cl2 was added and the aqueous phase was removed. The organic phase was washed halide-free with deionized water (AgNO3 test). The solution was filtered over a column filled with neutral Al2O3 and activated charcoal. The organic solvent was removed under reduced pressure and the reaction product finally dried under dynamic vacuum for 1-2 days at 80-90 C.

383.5 g

In water;

Step 1: Take 287.1g of lithium bis (trifluoromethanesulfonyl) imide (LiTFSI) completely dissolved in water to form an aqueous solution with a mass percentage concentration of 50%; Step 2: 191.1 g of 1-ethyl-3-methylimidazolium bromide (EMIBr) was completely dissolved in water to form an aqueous solution having a mass percentage concentration of 50% Step 3: mixing the aqueous solution products obtained in steps 1 and 2 to obtain a crude product; Step 4: The crude product is obtained in step 3, washed with water for 2 times, emulsified by heating and stirring, and heated to 60 DEG C for demulsification, and then high purity product is obtained after liquid separation; Step 5: The high-purity product obtained in Step 4 was vacuum-dried at 100 C for 8 hours to obtain 383.5 g of colorless liquid EMI · TFSI product (melting point: about -15 C), purity: 99.95%, water content: 80 ppm, .

References: [1]Inorganic Chemistry,2018,vol. 57,p. 2314 - 2319.
[2]Organic and Biomolecular Chemistry,2008,vol. 6,p. 2522 - 2529.
[3]Organic Letters,2009,vol. 11,p. 1523 - 1526.
[4]Chemical Communications,2010,vol. 46,p. 1488 - 1490.
[5]Molecules,2011,vol. 16,p. 5963 - 5974.
[6]Angewandte Chemie - International Edition,2012,vol. 51,p. 11483 - 11486.
Angew. Chem.,2012,vol. 124,p. 11650 - 11654,5.
[7]Organic and Biomolecular Chemistry,2013,vol. 11,p. 2534 - 2542.
[8]Patent: CN110878053,2020,A .Location in patent: Paragraph 0064; 0066.
[9]Patent: US2007/7137,2007,A1 .Location in patent: Page/Page column 4.
[10]Chemical Communications,2017,vol. 53,p. 11154 - 11156.
[11]Chemical Communications,2008,p. 4939 - 4941.
[12]Analytical Chemistry,2004,vol. 76,p. 2773 - 2779.
[13]Journal of the American Chemical Society,2005,vol. 127,p. 4976 - 4983.
[14]Journal of Materials Chemistry,2006,vol. 16,p. 1475 - 1482.
[15]Chemical Communications,2007,p. 2732 - 2734.
[16]Electrochimica Acta,2010,vol. 55,p. 7145 - 7151.
[17]Journal of Chemical and Engineering Data,2012,vol. 57,p. 875 - 881.
[18]Science China Chemistry,2012,vol. 55,p. 1519 - 1524.
[19]Journal of Molecular Liquids,2013,vol. 177,p. 361 - 368.
[20]Inorganic Chemistry,2013,vol. 52,p. 13167 - 13178.
[21]Dalton Transactions,2014,vol. 43,p. 568 - 575.
[22]Macromolecules,2013,vol. 46,p. 9464 - 9472.
[23]Journal of Molecular Liquids,2014,vol. 192,p. 191 - 198.
[24]Physical Chemistry Chemical Physics,2014,vol. 16,p. 23233 - 23243.
[25]Dalton Transactions,2016,vol. 45,p. 10151 - 10154.
[26]Patent: CN105985277,2016,A .Location in patent: Paragraph 0029; 0030; 0031; 0032; 0033; 0034.
[27]Journal of Chemical and Engineering Data,2018,vol. 63,p. 4484 - 4496.

3
[ 174899-82-2 ]
ethyl bis(trifluoromethanesulfonyl)imide [ No CAS ]
[ 616-47-7 ]
[ 7098-07-9 ]
[ 537031-78-0 ]

References: [1]Australian Journal of Chemistry,2004,vol. 57,p. 145 - 147.

4
[ 174899-82-2 ]
[ 616-47-7 ]
[ 1072-62-4 ]
[ 7098-07-9 ]
[ 693-98-1 ]

References: [1]Australian Journal of Chemistry,2004,vol. 57,p. 145 - 147.

5
[ 616-47-7 ]
[ 74-96-4 ]
[ 90076-65-6 ]
[ 174899-82-2 ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 1553 - 1557.
[2]Journal of Organic Chemistry,2007,vol. 72,p. 7790 - 7793.

6
1-ethyl-3-methylimidazolium bromide [ No CAS ]
[ 174899-82-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With bis(trifluoromethane)sulfonimide lithium; In acetone; for 24h;	79 g of 1-ETHYL-3-METHYLIMIDAZOLIUM bromide was added to 250 ml of acetone, and 76 G (1.1 eq. ) of lithium bis (trifluorosulfonyl) imide was added thereto and reacted for 24 hours, followed by filtering the reactant solution to remove salts. The resulting filtrate was distilled to remove acetone, giving an unpurified 1-ETHYL-3-METHYLIMIDAZOLIUM bis (trifluorosulfonyl) imide ionic liquid. To the unpurified 1-ethyl-3-methylimidazolium bis (TRIFLUOROSULFONYL) imide ionic liquid was added a mixed solution of ionic water and methyl alcohol (1V/3V) to prepare a product having a concentration of about 50%, followed by transferring to a reflux device of the continuous distillation extraction apparatus. Then, methylene chloride was added to a receiver (3V/W) and REFLUXED at 39 No. 40 C for about 12 hours. Then, the methylene chloride solution was collected from the receiver OF THE CONTINUOUS DISTILLATION E) DRACTION APPARATUS AND METHYLENE CHLORIDE WAS DISTILLED TO BE REMOVED, FOLLOWEA BY DRYING UNDER reduced pressure at 60C for 76 hours to remove water, thereby acquiring 1- ethyl-3-methylimidazolium bis (trifluorosulfonyl) imide ionic liquid. Yield : 100 g (95%), residual bromide ions: 2-100 ppm (before purification : 100 ppm), residual . SODIUM IONS : 1-5 PPM (BEFORE PURIFICATION : 30 PPM), , water: 200 ppm. To achieve high purity ionic liquids, the obtained 1-ethyl-3- METHYLIMIDAZOLIUM bis (TRIFLUOROUSDULFONYL) IMIDE IONIC LIQUID WAS REPEAUDLY PURIFIED. Yield : 99 g (99%), residual chloride ion : 1 ppm (before repeated cycles of PURIFICATION: 2 No. 20 PPM), RESIDUAL SODIUM IONS > 3 ppm (before repeated cycles of purification : 1-5 PPM), WATER : 200 ppm.

References: [1]Patent: WO2004/80974,2004,A1 .Location in patent: Page 15-16.

8
[ 554-95-0 ]
[ 6147-53-1 ]
[ 65039-08-9 ]
[ 174899-82-2 ]
[ 951026-20-3 ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 10334 - 10335.

9
[ 366-18-7 ]
[ 554-95-0 ]
[ 6147-53-1 ]
[ 174899-82-2 ]
(EMIm)[Co₂(trimesate)₄H₇(2,2′-bipyridyl)₂] [ No CAS ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 10334 - 10335.

10
[ 554-95-0 ]
[ 6147-53-1 ]
[ 174899-82-2 ]
Co₅(OH)2(OAc)8(H₂O)x [ No CAS ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 10334 - 10335.

11
[ 83978-39-6 ]
[ 174899-82-2 ]
[ 940301-63-3 ]

Yield	Reaction Conditions	Operation in experiment
81%	Product distribution / selectivity;	To 48.75 g (0.097 mol) of tris(diethylamino) n-butylaminophosphonium iodide obtained in B(h), an aqueous solution dissolving 28.7 g (0.100 mol) of LiTFSI in 200 ml of ultrapure water was added, and then the resultant mixture was stirred at 50C for 3 days. The resulting salt was extracted with 100 ml of CH2Cl2, and the water layer was further extracted with 50 ml of CH2Cl2. After five times of washing with ultrapure water, the resulting extracted solution was concentrated with a rotary evaporator and vacuum-dried at 90C, and then passed through an alumina column (developing solvent: CH2Cl2). The extracted solution was concentrated again with a rotary evaporator and vacuum-dried at 90C so as to obtain 54.59 g of a product; the yield was 85.8%. The resulting compound was identified with a nuclear magnetic resonance analyzer (BRUKER Ultra Shield 300 NMR Spectrometer, manufactured by BRUKER Limited.). The resulting spectral data are shown below. 1H-NMR (300 MHz, solvent: CDCl3, standard substance: tetramethylsilane) delta 3.14 (m, 12H) 2.99 (m, 4H) 1.54 (m, 4H) 1.33 (m, 4H) 1.22 (t, 18H) 0.97 (t, 6H) 19F-NMR (282 MHz, solvent: CDCl3, standard substance: CF3Cl) delta -78.75 (s, 6F) 31P-NMR (121 MHz, solvent: CDCl3, standard substance: triphenylphosphine) delta 43.85 (m, 1P) The structural formula is shown below (in the formula, the dashed lines show a conjugated structure). [Show Image] The melting point was measured with a differential scanning calorimeter (DSC8230, manufactured by Shimadzu Corp.). The melting point was 25.4C. The thermal decomposition temperature was measured with a thermal gravimetry analyzer (TG8120, manufactured by Rigaku Corp.). The 5% weight-loss temperature measured at a temperature rise rate of 10C/min was 362.5C. The electrical conductivity as measured with the AC impedance method (Electrochemical Measurement System HZ-3000, manufactured by Hokuto Denko Corp.) was 0.0642 Sm-1 at 50C. The potential window was -0.1 V to 4.8 V with respect to Li/Li+, which was obtained from a cyclic voltammogram measured with the Electrochemical Measurement System HZ-3000 manufactured by Hokuto Denko Corp. using Pt for a working electrode and a counter electrode and Li for a reference electrode. A CV curve of tris(diethylamino)di-n-butylaminophosphonium bistrifluoromethane sulfonylimide is shown in FIG. 3. To 3.8 g (0.0058 mol) of tris(diethylamino)di-n-butylaminophosphonium bistrifluoromethane sulfonyl imide, an aqueous solution dissolving 5 g of NaOH in 20 ml of H2O was added, and then the resulting reaction mixture was stirred at 50C for 14 hours. Subsequently, 50 ml of CH2Cl2 were added to the reaction mixture, and the resultant solution was separated. The organic layer was washed with 30 ml of ultrapure water three times, vacuum-concentrated, and vacuum-dried at 80C so as to obtain 3.7 g of a product; the yield was 96%. A similar experiment was carried out using ethylmethylimidazolium bistrifluoromethane sulfonylimide; the yield was 81 %.

References: [1]Patent: EP1956026,2008,A1 .Location in patent: Page/Page column 41; 42.

12
[ 945614-34-6 ]
[ 65039-09-0 ]
[ 60-29-7 ]
[ 75-00-3 ]
[ 174899-82-2 ]

Yield	Reaction Conditions	Operation in experiment
97.9%	at 80℃; for 3h;	A mixture of 1.32 g (9.0 mmol) of 1-ethyl-3-methylimidazolium chloride and 3.45 g (9.0 mmol) of triethyloxonium bis(trifluoromethylsulfonyl)imide from Example 3 is heated to 70-80 C. (temperature of the oil bath) and stirred for four hours under a nitrogen atmosphere. Volatile constituents are pumped off over the course of one hour under reduced pressure (7 Pa) at 70 C. (temperature of the oil bath), giving 3.45 g of a liquid. The yield of 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide is 97.9%, based on the 1-ethyl-3-methylimidazolium chloride employed. The product is investigated by NMR spectroscopy.1H NMR spectrum, ppm: 1.45 t (CH3); 3.83 s (CH3); 4.17 q (CH2); 7.37 m (CH); 7.43 m (CH); 8.57 br. s. (CH); 3JH,H=7.3 Hz.19F NMR spectrum, ppm: -78.91 s (CF3).

References: [1]Patent: US2009/36628,2009,A1 .Location in patent: Page/Page column 13.

13
[ 174899-82-2 ]
[ 1048670-57-0 ]
[ 1149760-68-8 ]

References: [1]European Journal of Organic Chemistry,2008,p. 2881 - 2886.

14
[ 376-73-8 ]
[ 6147-53-1 ]
[ 65039-08-9 ]
[ 174899-82-2 ]
[1-ethyl-3-methylimidazolium]2[Co₃(H₂O)4(hexafluoroglutarate)4] [ No CAS ]

References: [1]Dalton Transactions,2009,p. 1131 - 1135.

15
[ 377-38-8 ]
[ 6147-53-1 ]
[ 65039-08-9 ]
[ 174899-82-2 ]
[1-ethyl-3-methylimidazolium]2[Co(H₂O)2(tetrafluorosuccinate)2] [ No CAS ]

References: [1]Dalton Transactions,2009,p. 1131 - 1135.

16
[ 852616-00-3 ]
[ 82113-65-3 ]
[ 174899-82-2 ]

References: [1]Journal of Fluorine Chemistry,2009,vol. 130,p. 1183 - 1191.

17
[ 1202271-18-8 ]
[ 174899-82-2 ]
[ 1202271-19-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	In diethyl ether;	Example 5: Synthesis of 1-Ethyl-3-methylimidazolium fluorobutylsulfonate; In a 100 ml Schlenkvessel 3,00 g (0,0075 mol) Tetrabutylammonium ^n fluorobutylsulfonate and the same amount diethyl ether is solved and 2,93 g (0,0075 mol) 1-Ethyl-3-methylimidazolium bis(trifluoromethyl-sulfonyl)imide is added. The organic phase with diethyl ether is separated and the remaining phase is washed with diethyl ether several times. Afterwards the <n="34"/>product is liberated from the solvent under reduced pressure and a clear yellow liquid is obtained.Yield: 1 ,8 g (0,0068 mol), 90%.NMR-Data: 1H-NMR (400 MHz, CDCI3): delta= 1 ,46 (t, H6, 3H, JH-H=7,20 HZ); 1 ,74 (m, H9, 2H); 1 ,86 (m, H8, 2H); 2,77 (t, H10, 2H, JH-H = 7,82 Hz); 3,93 (s, H1 , 3H); 4,24 (q, H5, 2H); 4,30 (t, H7, 1H, JH-H = 6,17 Hz); 4,42 (t, H7, 1 H, JH-H =5,97 Hz, JN-F = 41 ,36 Hz); 7,41 (s, H4, 1 H); 7,44 (s, H3, 1 H); 9,75 (s, H2, 1 H) ppm.15 13C-NMR (100 MHz, CDCI3): delta= 15,58 (C-6); 21 ,52 (C-9); 29,54; 29,74 (C- 8); 36,33 (C-1 ); 45,06 (C-5); 51 ,42 (C-10); 83,12; 84,75 (C-7); 121 ,9 (C-4); 124,3 (C-3), 137,6 (C-2) ppm. 19F-NMR (376 MHz, CDCI3): delta=-218,6 ppm.

References: [1]Patent: WO2009/152902,2009,A2 .Location in patent: Page/Page column 32-33.

18
[ 174899-82-2 ]
[ 103816-76-8 ]

References: [1]Tetrahedron Letters,2010,vol. 51,p. 1976 - 1978.

19
[ 65039-09-0 ]
[ 90076-65-6 ]
[ 174899-82-2 ]

Yield	Reaction Conditions	Operation in experiment
62%	In acetonitrile; at 20℃; for 48h;	The ionic liquid EMI?TFSI- was synthesized by a one step methathesis: 1-ethyl-3-methylimidazoliumchloride EMI?Cl- (1.465 g, 0.01 mol) and lithium bis(trifluoromethanesulfonyl)imide (LiTFSI) (2.871 g, 0.01 mol) were dissolved in acetonitrile intwo separate vials. An anion-exchange reaction occurred after adding slowly (drop bydrop) LiTFSI solution in a 10 mL round-bottom flask containing the EMI?Cl- solution,whereby the mixture was precipitated. Then, the reaction mixture was stirred at 500 rpm atroom temperature for 48 h. After removal of the solvent, the mixture was washedrepeatedly with water until the Cl- could not be detected by addition of AgNO3 solution.The organic phase was collected in a vial and was passed at least twice through Celitesilica column with ethyl acetate to completely remove Cl-. After removal of the solvent,the final product was dried under vacuum to give a yellowish liquid (2.347 g, 62 %).

References: [1]Journal of Solution Chemistry,2015,vol. 44,p. 2332 - 2343.
[2]Synthetic Communications,2010,vol. 40,p. 1322 - 1332.
[3]Chemical Communications,2012,vol. 48,p. 1925 - 1927.
[4]Dalton Transactions,2013,vol. 42,p. 12908 - 12916.
[5]RSC Advances,2015,vol. 5,p. 81362 - 81370.
[6]Organic electronics,2017,vol. 51,p. 490 - 495.
[7]Chemical Communications,2018,vol. 54,p. 409 - 412.

20
C₇H₇N₂O₄^(1-)*C₁₂H₂₄KO₆⁽¹⁺⁾ [ No CAS ]
[ 174899-82-2 ]
[K(18C₆)₁][TFSA] [ No CAS ]

References: [1]Inorganica Chimica Acta,2010,vol. 363,p. 504 - 508.

21
2C₇H₇N₂O₄^(1-)*C₁₂H₂₄BaO₆⁽²⁺⁾ [ No CAS ]
[ 174899-82-2 ]
2C₂F₆NO₄S₂^(1-)*C₁₂H₂₄BaO₆⁽²⁺⁾ [ No CAS ]

References: [1]Inorganica Chimica Acta,2010,vol. 363,p. 504 - 508.

22
[ 936836-94-1 ]
[ 174899-82-2 ]
[ 1312355-38-6 ]

References: [1]Organometallics,2011,vol. 30,p. 3726 - 3731.

23
[(R)-1,1'-binaphthyl-2,2'-diyl]chlorophosphite [ No CAS ]
[ 174899-82-2 ]
[1-ethyl-2-(1,1'-(R(a))-binaphthyl-2,2'-dioxyphosphino)-3-methylimidazolium] [bis(trifluoromethylsulfonyl)amide] [ No CAS ]

References: [1]Organometallics,2011,vol. 30,p. 3726 - 3731.

24
[ 20667-12-3 ]
[ 174899-82-2 ]
[bis(1-ethyl-3-methylimidazol-2-ylidene)silver(I)] [bis(trifluoromethylsulfonyl)amide] [ No CAS ]

References: [1]Organometallics,2011,vol. 30,p. 3726 - 3731.

25
[ 35935-34-3 ]
[ 90076-65-6 ]
[ 174899-82-2 ]

References: [1]Chemistry of Materials,2010,vol. 22,p. 1203 - 1208.

26
[ 174899-82-2 ]
[ 1048670-57-0 ]

References: [1]Journal of Raman Spectroscopy,2011,vol. 42,p. 733 - 743.
[2]Physical Chemistry Chemical Physics,2016,vol. 18,p. 17037 - 17043.
[3]Journal of the American Chemical Society,2018,vol. 140,p. 16685 - 16696.
[4]Journal of Physical Chemistry A,2019,vol. 123,p. 6342 - 6349.

27
[ 174899-82-2 ]
[ 1048670-33-2 ]

References: [1]Journal of Raman Spectroscopy,2011,vol. 42,p. 733 - 743.

28
[ 623-26-7 ]
[ 15226-74-1 ]
tin(IV) iodide [ No CAS ]
[ 174899-82-2 ]
[Co(1,4-dicyanobenzene)2(bis(trifluoromethylsulfonyl)imide)2][SnI(Co(CO)4)2]2 [ No CAS ]

References: [1]Dalton Transactions,2012,vol. 41,p. 8455 - 8459.

29
[ 161282-96-8 ]
[ 174899-82-2 ]
[ 1389393-10-5 ]

References: [1]Inorganica Chimica Acta,2012,vol. 390,p. 8 - 11.

30
[ 1422393-53-0 ]
[ 174899-82-2 ]
[ 1422393-54-1 ]

References: [1]Chemistry - A European Journal,2013,vol. 19,p. 1042 - 1057.

31
[ 174899-82-2 ]
[ 189114-61-2 ]
[ 1422393-56-3 ]

References: [1]Chemistry - A European Journal,2013,vol. 19,p. 1042 - 1057.

32
[ 174899-82-2 ]
[ 1333-74-0 ]

References: [1]Journal of Physical Chemistry B,2013,vol. 117,p. 6782 - 6788.

34
[ 1600-27-7 ]
[ 63348-58-3 ]
[ 174899-82-2 ]
[bis(1,3-diethylimidazole-2-thione)mercury(II)chloride] [ No CAS ]

References: [1]Dalton Transactions,2013,vol. 42,p. 12908 - 12916.

35
[ 1148-79-4 ]
[ 90076-65-6 ]
[ 174899-82-2 ]
[Li(2,6-bis(2-pyridyl)pyridine)][bis(trifluoromethylsulfonyl)imide] [ No CAS ]

References: [1]Inorganic Chemistry,2013,vol. 52,p. 13167 - 13178.

36
[ 90076-65-6 ]
[ 145022-44-2 ]
[ 174899-82-2 ]

References: [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 13392 - 13396.
Angew. Chem.,2013,vol. 125,p. 13634 - 13638,5.

37
[ 7585-39-9 ]
[ 174899-82-2 ]
C₄₂H₇₀O₃₅*C₂F₆NO₄S₂^(1-)*C₆H₁₁N₂⁽¹⁺⁾ [ No CAS ]

References: [1]Journal of Inclusion Phenomena and Macrocyclic Chemistry,2014,vol. 79,p. 319 - 327.

38
uranyl(VI) nitrate [ No CAS ]
[ 78-50-2 ]
[ 7732-18-5 ]
octyl-(phenyl)-N,N-diisobutyl carbamoyl methylene phosphine oxide [ No CAS ]
[ 174899-82-2 ]
[UO₂(TOPO)₃NO₃NTf₂*2H₂O-H]⁺ [ No CAS ]
[UO₂(CMPO)₂(TOPO)NO_3*2H₂O]⁺ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With carbon dioxide; In acetonitrile; at 40℃; under 187519.0 Torr;Supercritical conditions; Flow reactor;	The stripping samples were obtained after extracting UO22+ from the aqueous phase by CMPOC2mimNTf2. The concentration of UO22+ was 0.004 mol L-1 in the C2mimNTf2 phase, which presented a light yellow resulting from the characteristic of the complex of UO22+ with CMPO. All stripping experiments were performed in a lab supercritical fluid extraction apparatus (100 mL, SEPAREX, France), the method of which was described elsewhere [23]. CO2 (99.95%, Reijiye, China) was used in all experiments. 0.5 mL C2mimNTf2 solution containing 0.004 mol L-1 of uranium was added in a 10-mL glass basket, which was fixed in the high-pressure extraction vessel with strong stirring. The stripping process was allowed to take place under dynamic extraction condition, in which the sc-CO2 and the modifier solution passed continuously through the extraction chamber. The flow rate of CO2 was fixed at 0.2 g min-1, and the modifier was the 0.05mol L-1 of TOPO-acetonitrile solution. When the stripping modus operandi was complete, the system was allowed to slowly depressurize and the IL sample was then removed from the cell and analyzed. The stripping efficiency was calculated based on the contents of UO22+ in the initial and the residue IL phases, which were analyzed by Inductively Coupled Plasma-Atomic Emission Spectrometer (ICP-AES, Leeman, USA) after microwave digestion. The mass spectra of the stripping product and the IL phases were measuredwith electrospray ionization (ESI/MS) on a Fourier transformion cyclotron resonance mass spectrometer, APEX IV (Bruker, Germany). After the stripping experiment, the extraction of UO22+ from the aqueous phase by the recovered IL phase was studied. 0.5 mL of the recovered C2mimNTf2 without addition of new CMPO and 0.5 mL of the aqueous solution containing 0.004 mol L-1 of UO2(NO3)2 were added into aplastic centrifuge tube, followed by vigorous shaking for 24 h. Then, the mixture was centrifuged (8000 r, 2 min) and the two phases were separated. The extraction efficiency was calculated based on the contents of UO22+ in the initial and the residual aqueous phases, which were analyzed by ICP- AES.

References: [1]Science China Chemistry,2015,vol. 58,p. 545 - 550.

39
C₆H₁₁N₂⁽¹⁺⁾*0.5C₂H₃O₂^(1-)*0.5C₂F₆NO₄S₂^(1-) [ No CAS ]
[ 143314-17-4 ]
[ 174899-82-2 ]