174899-66-2|1-Butyl-3-methylimidazolium Trifluoromethanesulfonate| Ambeed

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Structure of 174899-66-2

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Quality Control of [ 174899-66-2 ] Purity: 98% SDS Specification

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Product Details of [ 174899-66-2 ]

CAS No. :	174899-66-2
Formula :	C₉H₁₅F₃N₂O₃S
M.W :	288.29
SMILES Code :	C[N+]1=CN(CCCC)C=C1.O=S(C(F)(F)F)([O-])=O
MDL No. :	MFCD03427620
InChI Key :	FRZPYEHDSAQGAS-UHFFFAOYSA-M
Pubchem ID :	2734246

Safety of [ 174899-66-2 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301-H315-H319
Precautionary Statements:	P301+P310-P305+P351+P338
Class:	6.1
UN#:	2810
Packing Group:	Ⅲ

Computational Chemistry of [ 174899-66-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	18
Num. arom. heavy atoms	5
Fraction Csp3	0.67
Num. rotatable bonds	4
Num. H-bond acceptors	6.0
Num. H-bond donors	0.0
Molar Refractivity	59.5
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	74.39 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	-3.64
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	1.65
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.51
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.	0.65
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	0.89
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.61

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.61
Solubility	0.71 mg/ml ; 0.00246 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.	-2.83
Solubility	0.431 mg/ml ; 0.00149 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	-1.55
Solubility	8.16 mg/ml ; 0.0283 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	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
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.	-6.89 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	0.0
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	0.0
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	3.0 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<0.0
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)	2.07

Application In Synthesis of [ 174899-66-2 ]

* 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 [ 174899-66-2 ]

[ 174899-66-2 ] Synthesis Path-Downstream 1~35

1
[ 33454-82-9 ]
[ 79917-90-1 ]
[ 174899-66-2 ]

References: [1]ChemSusChem,2019,vol. 12,p. 4452 - 4460.
[2]Dalton Transactions,2017,vol. 46,p. 12185 - 12200.
[3]Journal of Physical Chemistry B,2003,vol. 107,p. 11749 - 11756.
[4]Organic and Biomolecular Chemistry,2008,vol. 6,p. 2522 - 2529.
[5]Organic and Biomolecular Chemistry,2019,vol. 17,p. 9336 - 9342.
[6]Chemistry - A European Journal,2012,vol. 18,p. 13600 - 13604.

2
[ 4316-42-1 ]
[ 333-27-7 ]
[ 174899-66-2 ]

Yield	Reaction Conditions	Operation in experiment
95%		4.1-First Variant:Methyl trifluoromethanesulfonate (C. D. Beard et al; J. Org. Chem; 1973, 38, 3673) (4.26 g; 26.0 mmol) was added drop by drop, under stirring, into a cold solution (0 C.) of 2-butyl-imidazolium (3.10 g; 25.0 mmol) in 20 mL of dichloromethane. The resulting mixture was stirred for 30 minutes. 1 drop of water was added and shaken for one more hour. The reaction mixture was treated with anhydrous sodium carbonate and the resulting suspension was shaken for 30 minutes. Filtering followed by evaporation of the solvent produced the desired BMI.CF3SO3, a light yellow liquid (6.84 g; 95% yield). RMN-1H (CDCl3) delta: 9.03 (1H, s, C-H imidazolium); 7.48 (1H, s, C-H imidazolium); 7.47 (1H, s, C-H imidazolium); 5 4.21 (2H, t, J=7.3 Hz, NCH2); 3.97 (3H, s, NCH3); 1.87 (2H, quintet, J=7.3 Hz, CH2); 1.36 (2H, sextet, J=7.3 Hz, CH2); 0.91 (3H, t, J=7.3 Hz, CH3).

References: [1]Molecules,2012,vol. 17,p. 5319 - 5338.
[2]Patent: US2008/45723,2008,A1 .Location in patent: Page/Page column 4.
[3]Organic Letters,2009,vol. 11,p. 1523 - 1526.
[4]Synthetic Communications,2010,vol. 40,p. 2483 - 2487.
[5]Applied Catalysis A: General,2010,vol. 372,p. 124 - 129.
[6]Journal of Physical Chemistry B,2004,vol. 108,p. 5113 - 5119.
[7]Journal of Chemical and Engineering Data,2010,vol. 55,p. 1774 - 1778.

3
[ 1493-13-6 ]
[ 342789-81-5 ]
[ 174899-66-2 ]

References: [1]Advanced Synthesis and Catalysis,2006,vol. 348,p. 243 - 248.

4
[ 2926-30-9 ]
[ 79917-90-1 ]
[ 174899-66-2 ]

References: [1]Physical Chemistry Chemical Physics,2003,vol. 5,p. 2790 - 2794.
[2]Journal of Physical Chemistry B,2004,vol. 108,p. 16593 - 16600.

5
[ 616-47-7 ]
[ 1493-13-6 ]
[ 71-36-3 ]
[ 174899-66-2 ]

Yield	Reaction Conditions	Operation in experiment
75%		4.2-Second Variant:1-Methyl-imidazolium (2.74 g; 33.3 mmol) was mixed together with n-butanol (2.47 g; 33.3 mmol) in 40 mL of dichloromethane and, under stirring and cooling in an ice bath, anhydrous sulfonic trifluoromethane (9.40 g; 33.3 mmol) was added drop by drop. After finishing the addition to the mixture, it was stirred for 1 hour at room temperature, to which a saturated aqueous solution of sodium carbonate (3.54 g; 33.3 mmol) was added. The solution was stirred for 30 minutes at room temperature. The phases were separated, with an organic dry phase that uses anhydrous sodium carbonate. The solvent was evaporated under vacuum and gently heated (50 C.), producing the desired BMI.CF3SO3 (7.19 g; 75% yield), identical to the material obtained in experiment 1.2.4.1

References: [1]Patent: US2008/45723,2008,A1 .Location in patent: Page/Page column 4.

6
[ 616-47-7 ]
[ 109-65-9 ]
[ 2926-27-4 ]
[ 174899-66-2 ]

References: [1]Australian Journal of Chemistry,2007,vol. 60,p. 946 - 950.
[2]Synlett,2007,p. 2065 - 2068.

7
[ 1493-13-6 ]
[ 85100-77-2 ]
[ 174899-66-2 ]

Yield	Reaction Conditions	Operation in experiment
	In acetone; at 20℃; for 24h;	General procedure: To a solution of the crude 1-butyl-3-methylimidazoliumbromide, obtained from the above reactions,in acetone (70 mL) was added hexafluorophosphoric acid (10.90 g,100.0 mmol). The reaction mixture was stirred for 24 h at room temperature. The resulting mixture was filtered. Evaporation of the solvent under reduced pressure afforded the corresponding 1-Butyl-3-methylimidazolium hexafluorophosphate. Same procedure was used except that trifluoro methane sulphonic acid (15.08 g,100.0 mmol) was used instead of hexafluorophosphoric acid. The resulting mixture was filtered. Evaporation of the solvent under reduced pressure afforded the corresponding imidazolium trifluromethanesulphonate.1-Butyl-3-methylimidazolium tetrafluoroborate was also prepared using the same procedure as above except that tetrafluoro boric acid (15.08 g, 100.0 mmol) was used in place of hexafluorophosphoric acid. Progress of the reaction was measured by TLC. Completion of the reaction was confirmed by 1HNMR.

References: [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 3453 - 3463.
[2]Tetrahedron Letters,2007,vol. 48,p. 5635 - 5639.
[3]Journal of Molecular Structure,2019,vol. 1198.

8
[ 1493-13-6 ]
[ 79917-90-1 ]
[ 174899-66-2 ]

References: [1]Chemical Communications,2006,p. 1828 - 1830.
[2]Journal of Molecular Liquids,2010,vol. 157,p. 43 - 50.

9
[ 1912-32-9 ]
[ 174899-66-2 ]

References: [1]Advanced Synthesis and Catalysis,2006,vol. 348,p. 243 - 248.

10
[ 4316-42-1 ]
[ 77-78-1 ]
[ 174899-66-2 ]

Yield	Reaction Conditions	Operation in experiment
84%		In einen 2 I Schlenkkolben werden 620,5 g (5 mol) 1-Butylimidazol vorgelegt und 630,5g (5 mol) Dimethylsulfat portionsweise zugegeben. Der Ansatz wird danach 15 Minuten nachgeruehrt. Der Kolbeninhalt wird in ein 5I Becherglas ueberfuehrt und zu einer Mischung von 860,3g (5 mol) Natriumtrifluormethansulfonat in 2 Liter Wasser gegeben. Sofort bildet sich das Produkt als eine zweite fluessige Phase. Nach einer Phasentrennung wird die waessrige Phase noch einmal mit 1 Liter CH2Cl2extrahiert, und das organische Extrakt von Methylenchlorid befreit. Beide Produktfraktionen werden vereinigt und ueber Nacht bei 60C am HV getrocknet. Man erhaelt 1-Butyl-3-methylimidazolium-trifluormethylsulfonat in 84 %iger Ausbeute. Zum qualitativen Nachweis auf Chloridreste, werden ca. 1 g des Produktes in ca. 5 ml Wasser geloest und mit 2 Tropfen konzentrierter Salpetersaeure angesaeuert. Zu dieser Loesung werden dann ca. 3-4 Tropfen Silbernitrat gegeben um etwaig vorhandenes Chlorid als Silberchlorid auszufaellen. Das Ausbleiben eines Silberchlorid-Niederschlags spricht fuer die komplette Abwesenheit von Halogenidionen. 1H-NMR (300 MHz, Aceton-d3):0,87 (3 H, tr, J=9,2 Hz, Hh); 1,29-1,38 (2 H, m, Hg); 1,90-2,00 (2 H, m, Hf); 4,04 (3 H, s, Hb); 4,35 (2 H, tr, J=9,3 Hz, He); 7,71;7,78 (je 1 H, s, Hc,d); 9,11 (1 H, s, Ha) ppm.

References: [1]Patent: EP1182196,2002,A1 .Location in patent: Page 14.

11
1-butyl-3-methylimidazolium chloride [ No CAS ]
[ 174899-66-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium trifluoromethansulfonate; In acetone; for 24h;	65 g of 1-butyl-3-methylimidazolium trifluoromethanesulfonate was added to 150 ml of acetone, and 70 g (1.1 eq. ) of potassium TRIFLUOROMETHANESULFONATE 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-BUTYL-3-METHYLIMIDAZOLIUM TRIFIUOROMETHANESUIFONATE ionic liquid. To the unpurified 1-butyl-3-methylimidazolium trifluoromethanesulfonate ionic liquid was added ionic water 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. 40C FOR ABOUT 36 HOURS. THEN, THE methylene chloride solution was COLLECTED FROM THE RECEIVER OF THE CONTINUOUS distillation extraction apparatus and methylene chloride was distilled to be removed, followed by drying under reduced pressure at 60 C for 76 hours to remove water, thereby acquiring 1-BUTYL-3-METHYLIMIDAZOLIUM TRIFLUOROMETHANESULFONATE IONIC LIQUID. Yield : 100 g (93%), residual chloride ions: 2 ~ 20 ppm (before purification: 3,500 ppm), residual potassium ions: 1 ~ 5 ppm (before purification: 300 ppm), water: 300 ppm. To achieve high purity ionic liquids, the obtained 1-BUTYL-3- METHYLIMIDAZOLIUM TRIFLUOROMETHANESULFONATE ionic liquid was repeatedly purified. Yield : 95 g (95%), residual chloride ions: 1-5 ppm (before repeated cycles of purification: 2-20 ppm), residual potassium ions < 3 ppm (before repeated cycles of purification: 1 No. 5 ppm), water: 300 ppm.

References: [1]Patent: WO2004/80974,2004,A1 .Location in patent: Page 13-14.

13
[ 79917-90-1 ]
[ 333-27-7 ]
[ 174899-66-2 ]

References: [1]Patent: WO2006/63656,2006,A1 .Location in patent: Page/Page column 24-25.
[2]Molecules,2012,vol. 17,p. 5319 - 5338.

14
[ 27607-77-8 ]
[ 79917-90-1 ]
[ 174899-66-2 ]

References: [1]Patent: WO2006/63656,2006,A1 .Location in patent: Page/Page column 27.
[2]Molecules,2012,vol. 17,p. 5319 - 5338.

15
[ 616-47-7 ]
[ 109-69-3 ]
[ 2926-27-4 ]
[ 174899-66-2 ]

References: [1]Molecules,2008,vol. 13,p. 149 - 156.

16
[ 74507-62-3 ]
[ 174899-66-2 ]
[ 952128-76-6 ]

References: [1]Chemical Communications,2007,p. 3467 - 3469.

17
[ 2926-30-9 ]
[ 85100-77-2 ]
[ 174899-66-2 ]

References: [1]Journal of Organic Chemistry,2012,vol. 77,p. 7291 - 7298.
[2]Chemistry - A European Journal,2012,vol. 18,p. 8230 - 8239.
[3]Journal of Chemical and Engineering Data,2008,vol. 53,p. 2408 - 2411.

18
[ 2926-27-4 ]
[ 85100-77-2 ]
[ 174899-66-2 ]

References: [1]Tetrahedron,2010,vol. 66,p. 1352 - 1356.

19
[ 65039-05-6 ]
Amberlist A-26 CF₃SO₃(-) form [ No CAS ]
[ 174899-66-2 ]

References: [1]Green Chemistry,2009,vol. 11,p. 1507 - 1510.

20
[ 2923-28-6 ]
[ 79917-90-1 ]
[ 174899-66-2 ]

References: [1]Synthetic Communications,2010,vol. 40,p. 1322 - 1332.

21
[ 1350726-58-7 ]
[ 51956-75-3 ]
[ 174899-66-2 ]
3-nitro-4-phenyl-1-tosylazetidin-2-yl-trifluoromethanesulfonate [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 8058 - 8061.

22
[ 1350726-58-7 ]
[ 174899-66-2 ]
3-nitro-4-phenylthietan-2-yl-trifluoromethanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium O,O-diethyl phosphorodithioate; In tetrahydrofuran; mineral oil; at 20℃; for 4h;Inert atmosphere;	General procedure: To a solution of Baylis-Hillman adduct 1 (5 mmol) in dry THF (4 mL) was added IBX (5 mmol) and stirred at rt for 5 h to get alpha,beta-unsaturated aldehyde 3. Then, to a solution of O,O-diethyl hydrogen phosphorodithioate 2 (5 mmol) in dry THF (5 mL) was added dropwise a suspension of NaH (10 mmol) in dry THF (20 mL) with stirring to rt. After the addition was complete and evolution of hydrogen gas (effervescence) had ceased, the reaction mixture was stirred at 60 C for 30 min and then cooled to rt. In this solution was added alpha,beta-unsaturated aldehyde 3 followed by [bmim]X-Y (5 mmol) and the reaction mixture was stirred at rt for 2-4 h. Water (30 mL) was added, the mixture was extracted with ether (3×30 mL), the combined organic layers were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography (hexane/EtOAc, 95:5) to afford an analytically pure sample of 6.

References: [1]Tetrahedron,2012,vol. 68,p. 2459 - 2464.

23
[ 38542-94-8 ]
[ 65039-05-6 ]
[ 174899-66-2 ]

References: [1]Molecules,2012,vol. 17,p. 4007 - 4027.

24
ammonium iodide [ No CAS ]
[ 13463-40-6 ]
tin(IV) iodide [ No CAS ]
[ 7704-34-9 ]
[ 174899-66-2 ]
[1-butyl-3-metylimidazolium]₆[S][{Fe(CO)₃}₄Sn₆I₁₀]₂ [ No CAS ]

References: [1]Chemistry - A European Journal,2012,vol. 18,p. 13600 - 13604.

25
[ 13463-40-6 ]
tin(IV) iodide [ No CAS ]
[ 174899-66-2 ]
[1-butyl-3-metylimidazolium]₂[{Fe(CO)₃}₄Sn₆I₁₀] [ No CAS ]

References: [1]Chemistry - A European Journal,2012,vol. 18,p. 13600 - 13604.

26
lithium chloride [ No CAS ]
[ 174899-66-2 ]
[3-butyl-1-methyl-1H-imidazol-3-ium]Li[trifluoromethanesulfonate]3 [ No CAS ]