21252-69-7|1-Octyl-1H-imidazole| Ambeed

Abstract: The chemical structure of nine imidazolium sulfonate and triflimide zwitterionic liquids (ZILs) were systematically tuned to increase their thermal stability for gas chromatography (GC)separations. Substituents for imidazolium and 2-phenylimidazolium cation systems, comprised of alkyl, benzyl, and oligoether groups of varying chain lengths, were studied as stationary phases in GC. Propanesulfonate, ethanesulfonate, and propanetriflimide anions were examined to understand the effect of linker length and nucleophilicity on ZIL thermal stability. Studies were conducted to assess film stability and thermal lability of ZIL stationary phases on fused silica capillaries when exposed to elevated temperatures for prolonged time periods. All stationary phases exhibited relatively poor film stability on untreated capillary surfaces, but most showed repeatable chromatographic retention after stepwise heating from 100 to 200°C. To understand the thermal degradation pathways of the ZILs, mass spectrometry (MS) was used to monitor the degradation/volatilization of the stationary phase when heated from 40-250°C. Salt-deactivated surfaces were effective at mitigating stationary phase instability, but were observed to participate in the degradation of alkyl functionalized ZILs via nucleophilic attack of the alkyl substituent. This was not observed for oligoether substituted ZILs. Imidazolium propanesulfonate ZILs all underwent degradation through the detachment of the anion system, resulting in the reformation of 1,3-propanesultone. Most ZIL stationary phases degraded below 230°C, but the cation substituent was observed to play a significant role in overall ZIL thermal stability. For the imidazolium propanetriflimide ZIL, degradation of the anion system occurred prior to the detachment of the entire anion system via elimination and occurred at around 245°C.

Keywords: gas chromatography ; stationary phase ; zwitterionic liquid ; thermal stability ; mass spectrometry

Purchased from AmBeed: 21252-69-7

Mesoporous Silica-Supported Ionic Liquids as Catalysts for Styrene Carbonate Synthesis from CO2

Agnieszka Siewniak ; Adrianna Forajter ; Katarzyna Szymańska Catalysts,2020,10(11):1363.

DOI: 10.3390/catal10111363

Abstract: Various types of mesoporous silica were used as carriers to synthesize a series of immobilized imidazolium-based ionic liquids. Their activity was tested in the synthesis of styrene carbonate from CO2 and styrene. This is one-pot process, whereby two stages are carried out in one reactor and there is no need to isolate the intermediate product, epoxide. A systematic study on the influence of parameters such as temperature, the reaction time, CO2 pressure, as well as the amount and type of catalyst used was carried out. A strong synergistic catalytic effect of ionic liquid and Lewis acid was observed in promoting this reaction. The addition sequence of regents and amount of immobilized catalyst were considered crucial for the synthesis of styrene carbonate from CO2 and styrene. The tested silica-supported ionic liquids gave an easily-recyclable system which under the most favorable conditions ([mtespim]Cl/@SiO2; ZnBr2, 0.1 mol%; 110 °C, 4 h, 1 MPa) can be reused without a significant loss of catalytic activity nor selectivity.

Keywords: cyclic carbonates ; silica-supported ionic liquids ; carbon dioxide ; mesoporous silica

Purchased from AmBeed: 21252-69-7

Product Details of [ 21252-69-7 ]

CAS No. :	21252-69-7
Formula :	C₁₁H₂₀N₂
M.W :	180.29
SMILES Code :	CCCCCCCCN1C=CN=C1
MDL No. :	MFCD00467256
Boiling Point :	No data available
InChI Key :	KLMZKZJCMDOKFE-UHFFFAOYSA-N
Pubchem ID :	161351

Safety of [ 21252-69-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Calculated chemistry of [ 21252-69-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	5
Fraction Csp3	0.73
Num. rotatable bonds	7
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	57.14
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	17.82 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.8
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	3.36
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.24
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.	1.92
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	2.67
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.8

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.9
Solubility	0.228 mg/ml ; 0.00127 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.	-3.41
Solubility	0.0698 mg/ml ; 0.000387 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	-3.63
Solubility	0.0424 mg/ml ; 0.000235 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	Yes
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	Yes
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	Yes
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.	-5.01 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	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	0.0 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)	1.73

Application In Synthesis [ 21252-69-7 ]

* 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 [ 21252-69-7 ]

[ 21252-69-7 ] Synthesis Path-Downstream 1~26

1
[ 64777-25-9 ]
[ 21252-69-7 ]

References: [1]Journal of Organic Chemistry,1957,vol. 22,p. 1323,1325.

2
[ 288-32-4 ]
[ 111-85-3 ]
[ 21252-69-7 ]

References: [1]European Journal of Medicinal Chemistry,1990,vol. 25,p. 449 - 454.

3
[ 288-32-4 ]
[ 111-83-1 ]
[ 21252-69-7 ]

Yield	Reaction Conditions	Operation in experiment
89%		A mixture of imidazole (1 .36 g, 20.0 mmol) and sodium hydroxide (0.80 g, 20.0 mmol) in DMSO was heated to 90 C for 2 h, and then cooled to room temperature. A solution of 1 -bromooctane (3.46 g, 19.0 mmol) in DMSO was added dropwise to the mixture. After stirring at room temperature for 3 h, the mixture was heated up slowly to 65 C for 16 h with constant stirring. The solution obtained was mixed with water and the product was extracted 4 times with diethyl ether. The diethyl ether phases were combined and dried with sodium sulfate. Diethyl ether was removed under vacuum and the intermediate (9) was obtained as yellow liquid (2.89 g, 89 %). 1 H NMR (DMSO-d6): delta 7.61 (s, 2H), 7.15 (s, 1 H), 6.87 (s, 1 H), 3.93 (t, 2H), 1 .68 (m, 2H), 1 .25 (m, 10H), 0.85 (t, 3H).
87.7%	With sodium hydroxide; In dimethyl sulfoxide; at 20 - 25℃;Inert atmosphere;	To a flask equipped with a stirrer, Add the thermometer to the three necked flask 0 · 440 g (11.0 mmol) of NaOH, 0.714 g (10.5 mmol) of imidazole and 10 mL of dimethylsulfoxide (DMSO) were stirred under nitrogen at 20 C to 25 C to give a clear solution. To this was added dropwise 1.93 g (10.0 mmol)Bromo octane, reaction 4 ~ 6 h, the reaction into 10 mL of water extracted with chloroform 3 X 10 mL, and then washed with water chloroform layer 4 ~ 5 times, and then dried with anhydrous MgS04, filtered to get the filtrate, Removal of chloroform yielded a pale yellow liquid, 1.58 g of N-octylimidazole, in 87.7% yield.
85%	With sodium hydroxide; In tetrahydrofuran; water;Reflux;	General procedure: A solution of imidazole 3 (30 mmol) in THF (60 mL) was treated with NaOH (25 mL, 40% aq) and the alkyl bromide (30 mmol), and the reaction was refluxed overnight. The solvent was evaporated and the crude reaction mixture was extracted with CH2Cl2 against water. The organic layer was washed with water, dried over MgSO4 and concentrated. The final product was distilled under vacuum (~5 mbar) to provide 4 as yellow oily liquid in 80-85% yield.

82.3%		General procedure: A mixture of imidazole (30 mmol, 2.04 g), potassiumhydroxide (30 mmol, 1.68 g) and dimethyl sulfoxide(10 mL) was stirred for 2 h at room temperature. Afterthat, alkyl bromide (25.0 mmol of 1-bromohexane, 1-bromooctane,1-bromodecane, 1-bromododecane, 1-bromotetradecane,1-bromohexadecane, or 1-bromooctadecane)was dropped in slowly and the mixture was stirred for anadditional 4 h. Upon completion, water (30 mL) was addedto the resulting mixture followed by extraction with chloroform(5 x 30 mL). The combined organic layer wasdried over anhydrous magnesium sulfate and the filtratewas concentrated under reduced pressure. The residue wassubjected to flash chromatography with ethyl acetate aseluent to give N-alkyl imidazole. The respective yields ofN-hexyl imidazole, N-octyl imidazole, N-decyl imidazole,N-dodecyl imidazole, N-tetradecyl imidazole, N-hexadecylimidazole and N-octadecyl imidazole are 84.6, 82.3, 81.2,80.5, 80.4, 79.8 and 79.6 %.
60%		Imidazole (3.41 g, 50 mmol) and NaH (1.34 g, 54 mmol) were dissolved in THF (10 mL) under N2 in an ice bath for 45 min, followed by addition of 1-bromooctane (9.65 g, 50 mmol). The solution was stirred for 24 h at room temperature and then concentrated under reduced pressure after filtration.The residue was purified by flash chromatography (SiO2; petroleum ether/ethyl acetate5 : 1 as eluent) to give 1 as alight yellow oil (5.97 g, 60 %). deltaH (CDCl3, 400 MHz) 7.42 (1H, s), 7.01 (1H, s), 6.87 (1H, s), 3.89 (2H, t, J 8.0), 1.76-1.73 (2H, m), 1.31-1.25 (10H, m), 0.87 (3H, t, J 7.2). deltaC (CDCl3, 100 MHz) 136.2, 128.4, 118.1, 46.4, 31.2, 30.6, 28.6, 28.5,26.0, 22.1, 13.6. m/z (ESI) 181 ([M + H]+). m/z 181.1708. HRMS (ESI) Anal. Calc. for C11H21N2 ([M + H]+) 181.1705.
		General procedure: These compoundswere obtained fromthe reaction of the sodium salt of imidazole and 1-bromoalkanes, as follows: to a 3-necked round-bottom flask, provided with a reflux condenser, dropping funnel, and inlet for dry nitrogen was added a solution of imidazole (7.49 g; 0.11 mol) in dry ethanol (25 mL). Small pieces of sodium (2.53 g, 0.11 mol), were slowly introduced, the mixture was vigorously stirred until the metal has dissolved and then heated under reflux for 2 h. The mixture was cooled to room temperature; the appropriate 1-bromoalkane (0.10 mol; 16.50 g, 17.91 g, 19.31 g, 22.12 g for R ¼ C6; C7; C8 and C10, respectively)was added slowly (ca. 30 min); then the mixture was refluxed for 2 h. The mixture was cooled to room temperature, the precipitated NaBr was filtered off; the ethanol evaporated, the residual oilwas washed with water, and then dried with anhydrous MgSO4. The N-(1-alkyl)imidazoles were purified by fractional distillation (yields before distillation ca. 98%); their purity was confirmed with 1H NMR spectroscopy (results not shown).
		General procedure: N-Hexadecylbromide (11.35 g, 37.2 mmol) was dissolved in dimethylformamide (DMF, 50 mL) and then added to a solution of the sodium salt of imidazole, which was formed by the reaction of imidazole (5.0 g, 74 mmol) with sodium hydride (2.66 g, 111 mmol) in DMF (50 mL). The mixture was heated at 60 C for 6 h, cooled, and diluted with water. After extraction with ethyl acetate (EtOAc), the extract was washed with brine and water, and then dried with sodium sulfate. The solvent was separated by reduced pressure distillation and N-alkylimidazole was obtained as a pale yellow oily product.
	With potassium hydroxide; In acetonitrile; for 4h;Reflux;	General procedure: N-Butylimidazole and N-octylimidazole were synthesized fol-lowing the procedure of literature [44]: To a round-bottomedflask, imidazole (6.0 g, 88 mmol), 1-bromobutane/1-bromooctane(90 mmol), acetonitrile (50 mL) and potassium hydroxide (9.9 g,177 mmol), were added in sequence. The reaction mixture wasrefluxed for 4 h and then cooled down to room temperature. Afterevaporating the solvent, the residue was purified by a flash col-umn chromatography utilizing ethyl acetate/methanol (v/v = 25:1)as eluent. The pure product of 1-butylimidazole/1-octylimidazolewas isolated as a pale yellow oil (?83%). N-Octylimidazole:1H NMR: (CDCl3): (ppm) = 0.87 (t, J = 6.5 Hz,3H, CH3), 1.28 (br, 10H, CH2), 1.77 (br, 2H, CH2), 3.92 (t, J = 7.2 Hz,2H, CH2), 6.90 (s, 1H, ImH), 7.04 (s, 1H, ImH), 7.45 (s, 1H, ImH).13CNMR (CDCl3): (ppm) = 13.9, 22.5, 26.4, 28.9, 29.0, 31.0, 31.6, 46.9,118.7, 129.2, 136.9.
	With sodium hydroxide; In acetone; at 20℃; for 12h;	N-alkylimidazoles were synthesized using a previously reported method with minor modification. Typically, to a solution of imidazole (1 mol equiv.) and sodium hydroxide (1 mol equiv.) in acetone (50 mE) was added 1 -bromoalkane (0.8 mol equiv.). After stirring at room temperature for 12 h, a Nal3r precipitate was filtered and acetone removed under reduced pressure. A residual oily mass was re-dissolved in dichloromethane and extracted three times with water. Finally, an organic phase was dried on anhydrous sodium sulfate and dicholoromethane was removed under reduced pressure to produce brown oil.

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4
3-Acetyl-1-octyl-3H-imidazol-1-ium; bromide [ No CAS ]
[ 21252-69-7 ]

References: [1]Chemical and Pharmaceutical Bulletin,1983,vol. 31,p. 1213 - 1221.

5
[ 288-32-4 ]
[ 629-27-6 ]
[ 21252-69-7 ]

References: [1]Russian Journal of Applied Chemistry,1996,vol. 69,p. 1841 - 1848.
[2]Journal of the American Chemical Society,2008,vol. 130,p. 12590 - 12591.
[3]Journal of Materials Chemistry A,2013,vol. 1,p. 6572 - 6578.
[4]RSC Advances,2018,vol. 8,p. 14623 - 14632.

6
[ 21252-69-7 ]
[ 79-11-8 ]
1-Carboxymethyl-3-octyl-3H-imidazol-1-ium; chloride [ No CAS ]

References: [1]Russian Journal of Applied Chemistry,1996,vol. 69,p. 1841 - 1848.

9
[ 111-83-1 ]
silver-salt of 1<i>H</i>-imidazole [ No CAS ]
[ 21252-69-7 ]

References: [1]Zhurnal Obshchei Khimii,1945,vol. 15,p. 189,192.
Chem.Abstr.,1946,p. 1800.

10
[ 21252-69-7 ]
[ 629-27-6 ]
[ 270908-51-5 ]

References: [1]Journal of Organometallic Chemistry,2000,vol. 598,p. 409 - 416.
[2]Journal of the American Chemical Society,2008,vol. 130,p. 12590 - 12591.

11
[ 21252-69-7 ]
[ 24463-19-2 ]
[ 668989-10-4 ]

References: [1]Journal of Molecular Structure,2004,vol. 697,p. 131 - 135.
[2]New Journal of Chemistry,2017,vol. 41,p. 12490 - 12505.

12
[ 21252-69-7 ]
[ 5324-30-1 ]
3-[2-(diethoxyphosphinyl)ethyl]-1-octyl-1H-imidazolium tetrafluoroborate [ No CAS ]

References: [1]Helvetica Chimica Acta,2004,vol. 87,p. 2549 - 2555.

13
[ 21252-69-7 ]
[ 5324-30-1 ]
3-[2-(diethoxyphosphinyl)ethyl]-1-octyl-1H-imidazolium hexafluorophosphate [ No CAS ]

References: [1]Helvetica Chimica Acta,2004,vol. 87,p. 2549 - 2555.

14
[ 21252-69-7 ]
[ 1186-10-3 ]
1-[3-(diethoxy-phosphoryl)-propyl]-3-octyl-3<i>H</i>-imidazol-1-ium; bromide [ No CAS ]

References: [1]Helvetica Chimica Acta,2004,vol. 87,p. 2549 - 2555.
[2]Chemistry Letters,2004,vol. 33,p. 524 - 525.

15
[ 21252-69-7 ]
[ 1186-10-3 ]
1-(3'-O,O-diethylphosphonyl-n-propyl)-3-octylimidazolium hexafluorophosphate [ No CAS ]

References: [1]Chemistry Letters,2004,vol. 33,p. 524 - 525.

16
[ 21252-69-7 ]
[ 67217-55-4 ]
C₅₃H₈₉N₂O₃₄⁽¹⁺⁾*C₇H₇O₃S^(1-) [ No CAS ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 1747 - 1749.

17
[ 21252-69-7 ]
[ 106-95-6 ]
1-propenyl-3-octylimidazolium bromide [ No CAS ]

References: [1]Journal of Chemical and Engineering Data,2006,vol. 51,p. 1274 - 1279.

18
[ 21252-69-7 ]
[ 38571-73-2 ]
C₃₉H₇₁N₆O₃⁽³⁺⁾*3Cl^(1-) [ No CAS ]

References: [1]Chemistry - A European Journal,2007,vol. 13,p. 3106 - 3112.

19
[ 21252-69-7 ]
[ 105-58-8 ]
bis(1-octyl-2-imidazolyl)ketone [ No CAS ]

References: [1]Organic Letters,1999,vol. 1,p. 2121 - 2124.

20
[ 21252-69-7 ]
[ 26127-08-2 ]
1-[(1R,2S,5R)-(-)-menthoxymethyl]-3-octylimidazolium chloride [ No CAS ]

References: [1]New Journal of Chemistry,2007,vol. 31,p. 879 - 892.
[2]Journal of Molecular Liquids,2017,vol. 242,p. 336 - 348.

21
[ 21252-69-7 ]
bis(1-octyl-2-imidazolyl)(1-trityl-4-imidazolyl)carbinol [ No CAS ]

References: [1]Organic Letters,1999,vol. 1,p. 2121 - 2124.

22
[ 21252-69-7 ]
C₁₄H₂₈BN₂O₂⁽¹⁺⁾*Br^(1-) [ No CAS ]

References: [1]Journal of Chemical and Engineering Data,2006,vol. 51,p. 1274 - 1279.

23
[ 21252-69-7 ]
3-[3-(diethoxyphosphinyl)propyl]-1-octyl-1H-imidazolium tetrafluoroborate [ No CAS ]

References: [1]Helvetica Chimica Acta,2004,vol. 87,p. 2549 - 2555.

24
[ 21252-69-7 ]
1-(3'-O,O-diethylphosphonyl-n-propyl)-3-octylimidazolium hexafluorophosphate [ No CAS ]

References: [1]Helvetica Chimica Acta,2004,vol. 87,p. 2549 - 2555.

25
[ 111-83-1 ]
dipotassium-salt of <1,3,4>thiadiazolidine-2,5-dithione [ No CAS ]
[ 21252-69-7 ]

References: [1]Chemical and Pharmaceutical Bulletin,1983,vol. 31,p. 1213 - 1221.

26
[ 21252-69-7 ]
[ 77-78-1 ]
[ 244193-52-0 ]

Yield	Reaction Conditions	Operation in experiment
94%		In einen 2 I Schlenkkolben werden 830,5 g (5 mol) 1-Octylimidazol vorgelegt und 630,5g (5 mol) Dimethylsulfat portionsweise zugegeben. Der Ansatz wird danach 15 Minuten nachgeruehrt. Der Kolbeninhalt wird danach in ein 5I Becherglas ueberfuehrt und zu einer Mischung von 548,0g (5 mol) Natriumtetrafluoroborat in 2 Liter Wasser gegeben. Sofort bildetsich das Produkt als 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 60°C am HV getrocknet. Man erhaelt 1-Octyl-3-methylimidazoliumtetrafluoroborat in 94 percentiger Ausbeute. Zum qualitativen Nachweis auf Chloridreste, werden ca. 1 ml des Produktes mit ca. 5 ml Wasser versetzt 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 Chloridresten. [26.1] 1H-NMR (300 MHz, CDCl3):delta=9.3 ppm (s,1H,Ha); delta=7.26 ppm (d,1H,Hc); delta=7.24 ppm (d,1H,Hd); delta=4.1 ppm (t,2H,He); delta=3.9 ppm (s,2H,Hb); delta=1.6 ppm (m,2H,Hf); delta=1.2 ppm (m,10H,Hg,h,i,j,k); delta=0.8 ppm (t,3H,HI).13C-NMR (75 MHz, CDCl3):delta=137 ppm (C1); delta=124-122 ppm (C3,C4); delta=48 ppm (C5); delta=35 ppm (C2); delta=29-24 ppm (C6-C10); delta=20 ppm (C11); delta=13 ppm (C12).19F-NMR (281 MHz, CDCl3):delta= -151,3 ppm (d, 1J(BF)= 22 Hz)

References: [1]Patent: EP1182196,2002,A1 .Location in patent: Page 12, 13.

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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Application In Synthesis [ 21252-69-7 ]

[ 21252-69-7 ] Synthesis Path-Downstream 1~26

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