[ CAS No. 33529-01-0 ] {[proInfo.proName]}

Name: 33529-01-0|1-Hexylimidazole|95%
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Quality Control of [ 33529-01-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 33529-01-0 ]

Product Details of [ 33529-01-0 ]

CAS No. :	33529-01-0	MDL No. :	MFCD07636719
Formula :	C₉H₁₆N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KGWVFQAPOGAVRF-UHFFFAOYSA-N
M.W :	152.24	Pubchem ID :	3015660
Synonyms :

Calculated chemistry of [ 33529-01-0 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.67
Num. rotatable bonds :	5
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	47.52
TPSA :	17.82 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.61 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.34
Log Po/w (XLOGP3) :	2.28
Log Po/w (WLOGP) :	2.46
Log Po/w (MLOGP) :	1.32
Log Po/w (SILICOS-IT) :	1.92
Consensus Log Po/w :	2.06

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.23
Solubility :	0.903 mg/ml ; 0.00593 mol/l
Class :	Soluble
Log S (Ali) :	-2.29
Solubility :	0.778 mg/ml ; 0.00511 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.8
Solubility :	0.24 mg/ml ; 0.00157 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.46

Safety of [ 33529-01-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 33529-01-0 ]

* 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 [ 33529-01-0 ]

[ 33529-01-0 ] Synthesis Path-Downstream 1~88

1
[ 288-32-4 ]
[ 544-10-5 ]
[ 33529-01-0 ]

Reference： [1]European Journal of Medicinal Chemistry,1990,vol. 25,p. 449 - 454
[2]Catalysis Today,2012,vol. 187,p. 108 - 114
[3]ChemCatChem,2015,vol. 7,p. 616 - 624

2
[ 288-32-4 ]
[ 111-25-1 ]
[ 33529-01-0 ]

Yield	Reaction Conditions	Operation in experiment
84.6%		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 %. 1H NMR (Bruker Avance III500, 500 MHz, CDCl3) N-hexyl imidazole: delta 7.42 (s,-NCHN-), 7.01 (s, -NCHCHN-), 6.87 (s, -NCHCHN-),3.88 (t, -NCH2-), 1.73 (m, -NCH2CH2-), 1.25-1.27 (m,-NCH2CH2(CH2)3-), 0.85 (t, -CH2CH3).
79%		General procedure: Imidazole (3)/benzimidazole(5) (10 mmol) was dissolved in 10 ml of DMSO and solid NaOH(15 mmol) was then added it. The resulting pale yellow suspensionwas stirred in air at room temperature for 1.5 h, after which, thealkyl bromides or benzyl chlorides (15 mmol) were added andallowed to react until completion (TLC). Water (50 ml) was thenadded and the products were extracted with ethyl acetate. Combinedorganic layers were washed several times with water, thenwith brine, dried over Na2SO4 and subjected to chromatographicpurification over silica (100-200 mesh) using MeOH: EtOAc 5:95(v/v) as the mobile phase. Compounds 4a-f were isolated as yellowoils whereas, the compounds 7a-e were white solid. Spectroscopic data of the N-alkyl imidazoles are in accord with earlier literatureand thus are not shown here [30].

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 5322 - 5326
[2]Dalton Transactions,2013,vol. 42,p. 1385 - 1393
[3]Journal of Physical Chemistry B,2010,vol. 114,p. 7312 - 7319
[4]Journal of Surfactants and Detergents,2016,vol. 19,p. 681 - 691
[5]Physical Chemistry Chemical Physics,2010,vol. 12,p. 1764 - 1771
[6]New Journal of Chemistry,2007,vol. 31,p. 879 - 892
[7]Polyhedron,2017,vol. 127,p. 68 - 83
[8]New Journal of Chemistry,2012,vol. 36,p. 702 - 722
[9]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2863 - 2865
[10]Inorganic Chemistry,2017,vol. 56,p. 7558 - 7565
[11]Helvetica Chimica Acta,2004,vol. 87,p. 2742 - 2749
[12]Journal of Organic Chemistry,1985,vol. 50,p. 4888 - 4893
[13]Chemistry Letters,2005,vol. 34,p. 442 - 443
[14]Journal of Materials Chemistry,2011,vol. 21,p. 12280 - 12287
[15]Applied Catalysis A: General,2010,vol. 390,p. 235 - 244
[16]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 423 - 427
[17]Journal of the Chinese Chemical Society,2013,vol. 60,p. 745 - 754
[18]Chemical Biology and Drug Design,2014,vol. 83,p. 278 - 288
[19]Molecules,2014,vol. 19,p. 11741 - 11759
[20]RSC Advances,2015,vol. 5,p. 2869 - 2881
[21]RSC Advances,2015,vol. 5,p. 57968 - 57974
[22]RSC Advances,2015,vol. 5,p. 21865 - 21876

3
3-Acetyl-1-hexyl-3H-imidazol-1-ium; bromide [ No CAS ]
[ 33529-01-0 ]

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

4
3-Benzoyl-1-hexyl-3H-imidazol-1-ium; bromide [ No CAS ]
[ 33529-01-0 ]

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

5
[ 74-83-9 ]
[ 33529-01-0 ]
[ 85100-78-3 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1983,vol. 48,p. 103 - 111
[2]Collection of Czechoslovak Chemical Communications,1985,vol. 50,p. 845 - 853

6
[ 26127-08-2 ]
[ 33529-01-0 ]
1-[(1R,2S,5R)-(-)-menthoxymethyl]-3-hexylimidazolium chloride [ No CAS ]

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

7
[ 111-25-1 ]
(+-)-6,6,9-trimethyl-7,8,9,10-tetrahydro-6<i>H</i>-benzo<<i>c</i>>chromene-1,3-diol [ No CAS ]
[ 33529-01-0 ]

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

8
[ 33529-01-0 ]
C₁₂H₄N₄^(1-)*C₁₀H₁₉N₂⁽¹⁺⁾ [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1983,vol. 48,p. 103 - 111

9
[ 33529-01-0 ]
C₁₂H₄N₄*2C₁₂H₄N₄^(1-)*2C₁₀H₁₉N₂⁽¹⁺⁾ [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1983,vol. 48,p. 103 - 111

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 51 STR67 In the same manner as in Example 44, from 0.6 g of 7-[2-(2-tert-butoxycarbonyl)prop-2-oxyimino-2-(2-tritylaminothiazole-4-yl)acetamide]-3-iodomethyl-3-cephem-1-oxido-4-carboxylic acid p-methoxybenzyl ester (syn-isomer) and 80 mg of 1-n-hexylimidazole was obtained 360 mg of 7-[2-(2-tert-butoxycarbonyl)prop-2-oxyimino-2-(2-tritylaminothiazole-4-yl)acetamide]-3-(3-n-hexyl-1-imidazoliomethyl)-3-cephem-1-oxido-4-carboxylic acid p-methoxybenzyl ester.iodide (syn-isomer). NMR delta ppm (CDCl3): 0.88(3H,m), 1.05-2.15(8H,m), 1.39(9H,s), 2.04(6H,s), 3.76(3H,s), 5.02(1H,m), 5.43(2H,m), 6.14(1H,m), 6.48(1H,s), 7.02(4H,m), 7.24(15H,s), 7.73(1H,s), 9.64(1H,s).

11
[ 288-32-4 ]
[ 638-45-9 ]
[ 33529-01-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With C12H18ClCuN4O(1+)*ClO4(1-); caesium carbonate; In acetonitrile; at 80℃; for 24h;Inert atmosphere;	General procedure: In a flame-driedvessel, equipped with a magnetic stirrer, under argon atmosphere,were added 0.3 mL of anhydrous acetonitrile, the nucleophile (imidazoleor benzimidazole - 0.75 mmol, 1.5 eq.), the electrophile(alkyl or aryl iodide - 0.5 mmol, 1 eq.), the base (1 mmol, 2 eq.),and the copper catalyst (0.05 mmol - 10% loading). The reactionvessel was heated to 80 C and left under stirring for 24 h. Thereaction mixture was then allowed to cool to room temperature,diluted with dichloromethane (5 mL) and filtered through celite. The celitepad was further washed with dichloromethane(2 x 5 mL). The combined organic phases were washed with water(2 x 5 mL) and brine (2 x 5 mL). The organic solvents were thenremoved in vacuo to yield the crude product, which was purifiedby flash column chromatography on silica gel using a gradient mixtureof ethyl acetate/petroleum ether as eluent. The 1H and 13CNMR spectral data for all N-arylatedimidazoles and benzimidazolesare in full agreement with those reported to literature [57-61].

Reference： [1]Polyhedron,2019,vol. 165,p. 22 - 30
[2]New Journal of Chemistry,2018,vol. 42,p. 10467 - 10471
[3]Journal of the American Chemical Society,2008,vol. 130,p. 12590 - 12591
[4]Journal of Materials Chemistry A,2013,vol. 1,p. 6572 - 6578

12
[ 638-45-9 ]
[ 33529-01-0 ]
[ 87266-39-5 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 12590 - 12591

13
[ 111-25-1 ]
[ 5587-42-8 ]
[ 33529-01-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	In tetrahydrofuran; at 65℃;	To a slurry mixture of ISS (5.00 g, 55.5 mmol) from Example 1 in a standard grade THF (50 mL) in a 100 mL round bottom flask was added 1-bromohexane (9.16 g, 55.5 mmol). The resulting mixture was heated overnight at reflux (65 C.) while stirring. The mixture was then cooled and the solids were removed by filtration. The resulting filtrate was concentrated, and the remaining yellow oil further concentrated under vacuum to produce the desired 1-hexylimidazole. 1H NMR (not shown) confirmed the identity of the product to be 1-hexylimidazole (Yield=7.80 g, 92%).

Reference： [1]Patent: US2009/171098,2009,A1 .Location in patent: Page/Page column 6
[2]RSC Advances,2015,vol. 5,p. 87200 - 87205

14
[ 33529-01-0 ]
[ 265987-26-6 ]
[ 1144032-56-3 ]

Reference： [1]Chemical Communications,2009,p. 1133 - 1135

15
[ 33529-01-0 ]
[ 2530-87-2 ]
[ 1188304-48-4 ]

Reference： [1]Green Chemistry,2009,vol. 11,p. 455 - 458

16
chloro(1,3-di(dodecyl)imidazol-2-ylidene)gold(I) [ No CAS ]
silver nitrate [ No CAS ]
[ 33529-01-0 ]
(1,3-di(dodecyl)imidazol-2-ylidene)(1-hexylimidazole)gold(I) nitrate [ No CAS ]

Reference： [1]Dalton Transactions,2009,p. 7121 - 7131

17
chloro(1,3-di(octadecyl)imidazol-2-ylidene)gold(I) [ No CAS ]
silver nitrate [ No CAS ]
[ 33529-01-0 ]
(1,3-di(octadecyl)imidazol-2-ylidene)(1-hexylimidazole)gold(I) nitrate [ No CAS ]

Reference： [1]Dalton Transactions,2009,p. 7121 - 7131

18
[ 288-32-4 ]
[ 16156-50-6 ]
[ 33529-01-0 ]

Reference： [1]Green Chemistry,2009,vol. 11,p. 1955 - 1960
[2]Catalysis Communications,2010,vol. 11,p. 470 - 475

19
[ 33529-01-0 ]
N-hexylimidazolium tetrafluoroborate [ No CAS ]

Reference： [1]Green Chemistry,2009,vol. 11,p. 1955 - 1960

20
[ 33529-01-0 ]
[ 107-05-1 ]
[ 1217895-95-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	at 80℃; for 1h;Inert atmosphere; Microwave irradiation;	General procedure: These ILs were obtained by the reaction of the appropriate N-(1-alkyl)imidazole with allyl chloride (3-chloro-1-propene), under microwave (MW) irradiation as follows, for 1-allyl-3-(1-hexyl) imidazolium chloride, AlHxImCl; 1-allyl-3-(1-heptyl)imidazolium chloride, AlHpImCl; 1-allyl-3-(1-octyl)imidazolium chloride AlOcImCl; 1-allyl-3-(1-decyl)imidazoliumchloride, AlDcImCl. N-(1-alkyl) imidazole (0.22 mol; 33.49 g, 36.58 g, 39.66 g, 45.8 g for R ¼ C6; C7; C8 and C10) and 3-chloro-1-propene (0.25 mol; 19.13 g) were mixed in a glass reactor, provided with a reflux condenser and inlet for dry nitrogen; the reactor was introduced in the cavity of the MWapparatus (Discover model DU-8316; CEM; Matthews) and irradiated under vigorous stirring for 1 h; 20W, 80 C. The product was dissolved in ethyl acetate (100 mL); the solution placed in a freezer (phase separation of the IL); the upper layer discarded; this process was repeated thrice. After removal of ethyl acetate, the IL was dried at 110 C,1 mmHg for 12 h. The yields were 98 1% (light yellow viscous liquid in all cases). 2.2.3.1 1-Allyl-3-(1-hexyl)imidazolium chloride Light-yellow, viscous liquid. 1H NMR for C12H21N2Cl: 0.88 (3H, t, J = 7.0, H13), 1.27-1.40 (6H, m, H12), 1.78-1.97 (2H, m, H11), 4.34 (2H, t, J = 7.7, H10), 5.07 (2H, d, J = 6.6, H6), 5.46 (1H, d, J = 4.2, H9), 5.49 (1H, s, H8), 6.03 (1H, m, H7) 7.25 (2H, s, H4 & H5), 10.98 (1H, s, H2). Calcd. for C12H21N2ClO4: C, 49.2%; H, 7.2%; N, 9.6%. Found: C, 49.1%; H, 7.2%; N, 9.7%.

Reference： [1]Dyes and Pigments,2013,vol. 96,p. 16 - 24,9
[2]Physical Chemistry Chemical Physics,2010,vol. 12,p. 1764 - 1771
[3]Journal of Materials Chemistry,2011,vol. 21,p. 6864 - 6868
[4]Carbohydrate Polymers,2012,vol. 87,p. 1058 - 1064

21
[ 111-25-1 ]
[ 33529-01-0 ]
1,3-dihexyl-1H-imidazol-3-ium bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	In toluene; at 40℃; for 24h;Schlenk technique; Inert atmosphere;	General procedure: The ligands (except 3) were all synthesized by adaptation of the methods of Starikova et al. [20]. A typical and generic procedure is described. Spectroscopic and analyses data are presented. N-monosubstituted azole (0.1mmol) and dry toluene were placed in a two-neck flask and stirred until a homogeneous solution was formed; then alkyl halide (0.3mmol) was added drop wise with continuous stirring. After addition of the alkyl halide, the mixture was stirred while heating at 40C for 24h. The solvent was removed and the ligand was dried under vacuum.2.2.8 1,3-Dihexylimidazolium bromide (9) Light yellowish oil. Yield (2.32 g, 99%). IR (ATR cm-1): 3416, 2928, 2859, 1563, 1508, 1459, 1378, 1231, 1162, 1108, 1078, 1056, 917, 812, 728, 642, 562; deltaH (400 MHz, CDCl3): 0.83 (6H, t, J 6.8 Hz, CH3), 1.34 (4H, m, CH2), 1.73 (4H, m, CH2), 1.86 (4H, m, CH2), 2.26 (4H, m, CH2), 4.28 (4H, t, J 7.1 Hz, NCH2), 7.48 (2H, s, NCH) and 10.36 ppm (1H, s, CH), deltaC (100 MHz, CDCl3): 13.90 (CH3), 22.37 (CH2), 31.07 (CH2), 32.78 (CH2), 41.02 (CH2), 50.04 (NCH2), 128.19 (NCH), 129.01 (NCH), 137.83 ppm; m/z (ESI) 236.8 (M+-Br-) HRMS (ESI) calcd for C15H29BrN2, 237.23307 (M+-Br-), found, 237.23309 (M+-Br-).

Reference： [1]Journal of Molecular Catalysis A: Chemical,2014,vol. 385,p. 98 - 105
[2]Angewandte Chemie - International Edition,2010,vol. 49,p. 5322 - 5326
[3]Dalton Transactions,2013,vol. 42,p. 1385 - 1393
[4]Zeitschrift fur Anorganische und Allgemeine Chemie,2017,vol. 643,p. 81 - 86

22
[ 106-93-4 ]
[ 33529-01-0 ]
1,2-bis[N-(N'-hexylimidazolium)]ethane dibromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	In acetonitrile; for 72h;Reflux;	A solution of <strong>[33529-01-0]1-hexylimidazole</strong> (3.35 g, 22 mmol) and 1,2-dibromoethane (2.07 g, 11 mmol) in MeCN (20 mL) was refluxedfor 3 days. After cooling to room temperature, the precipitate wasfiltered and washed with THF three times. Drying in a vacuum ovengave colorless crystalline bromide salt (3.51 g, 65%). A solution ofthe bromide salt and NaI (4 equiv.) in deionized water was stirredfor 24 h at ambient temperature. The precipitate was filtered anddrying in a vacuum oven gave a colorless crystalline solid BII-6(3.92 g, 93% from the bromide salt). MP 208-209 C. 1H NMR(500 MHz, CDCl3, 23 C): delta 0.89 (t, J 8, 6H), 1.34 (m, 12H), 1.96 (m,4H), 4.26 (t, J 8, 4H), 5.29 (s, 4H), 7.47 (t, J 1.5, 2H), 8.51 (t, J 1.5,2H), 10.1 (s, 2H). 13C NMR (125 MHz, CDCl3, 23 C): delta 14, 22, 26, 30,31, 48, 51, 122, 124, 136.

Reference： [1]Journal of Physical Chemistry B,2010,vol. 114,p. 7312 - 7319
[2]Organic electronics,2017,vol. 48,p. 241 - 247
[3]RSC Advances,2019,vol. 9,p. 3972 - 3978
[4]Journal of Materials Chemistry,2011,vol. 21,p. 12280 - 12287

23
[ 107-04-0 ]
[ 33529-01-0 ]
1-(2-chloroethyl)-3-hexylimidazolium hexafluorophosphate [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,2011,vol. 696,p. 263 - 268

24
[ 935-02-4 ]
[ 100-52-7 ]
[ 33529-01-0 ]
[ 1268469-18-6 ]

Yield	Reaction Conditions	Operation in experiment
52%	at 20 - 25℃; for 144h;	General procedure: 4.3.1. 2-Benzoyl-3-(1-methyl-1H-imidazol-2-yl)-3-phenylpropanenitrile (5a). To a mixture of cyanoacetylene 2a (0.127 g, 1 mmol) and benzaldehyde (3a; 0.106 g, 1 mmol) was added on stirring 1-methylimidazole (1a; 0.082 g, 1 mmol). The reaction mixture was stirred at 20-25 for 24 h. Column chromatography afforded propanenitrile 5a (0.171 g, 54%) as a faintly colored powder, mp 170-172 C (diastereomers ratio being 10:2.0).

Reference： [1]Tetrahedron,2011,vol. 67,p. 1288 - 1293

25
[ 33529-01-0 ]
[ 616-38-6 ]
[ 1208169-07-6 ]

Yield	Reaction Conditions	Operation in experiment
83%	at 80 - 90℃;Neat (no solvent);	A screw-top pressure tube was charged with dimethyl carbonate (3.0 mL), 1-alkylimidazole (2.0 mL) and a stir bar. It wassealed and heated for 30-70 h at 80-90 C to give a brown oil, whichwaswashed with diethyl ether (3 x 10 mL). Itwas purified by recrystallization in acetonitrile to give a yellow solid, which was dried in vacuo to give the product (Scheme 2).

Reference： [1]Journal of Organometallic Chemistry,2011,vol. 696,p. 2116 - 2121

26
[ 628-89-7 ]
[ 33529-01-0 ]
[ 1191399-87-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	In toluene; at 80℃; for 0.333333h;Microwave irradiation;	General procedure: 1-Hexylimidazole (1 eq) and the appropriate alkyl halide (1 eq) were placed in a closed vessel and exposed to irradiation for 20 min at 80 C using a microwave irradiation. The product was then collected as described in the conventional procedure outlined earlier.

Reference： [1]Molecules,2018,vol. 23
[2]Synthetic Communications,2011,vol. 41,p. 2455 - 2460

27
[ 33529-01-0 ]
[ 1191399-94-6 ]

Reference： [1]Synthetic Communications,2011,vol. 41,p. 2455 - 2460

28
[ 33529-01-0 ]
[ 1310683-58-9 ]

Reference： [1]Journal of Materials Chemistry,2011,vol. 21,p. 6864 - 6868

29
[ 33529-01-0 ]
1,2-bis[N-(N'-hexylimidazolium)]ethane bis(hexafluorophosphate) [ No CAS ]

Reference： [1]Journal of Materials Chemistry,2011,vol. 21,p. 12280 - 12287

30
[ 33529-01-0 ]
C₂₁H₃₈N₄⁽²⁺⁾*2F₆P^(1-) [ No CAS ]

Reference： [1]Journal of Materials Chemistry,2011,vol. 21,p. 12280 - 12287

31
[ 33529-01-0 ]
C₂₀H₃₂⁽²⁾H₄N₄⁽²⁺⁾*2F₆P^(1-) [ No CAS ]

Reference： [1]Journal of Materials Chemistry,2011,vol. 21,p. 12280 - 12287

32
[ 33529-01-0 ]
[ 109-64-8 ]
2Br^(1-)*C₂₁H₃₈N₄⁽²⁺⁾ [ No CAS ]

Reference： [1]Journal of Materials Chemistry,2011,vol. 21,p. 12280 - 12287

33
[ 1633-83-6 ]
[ 33529-01-0 ]
[ 1207853-19-7 ]

Reference： [1]Applied Catalysis A: General,2010,vol. 390,p. 235 - 244
[2]RSC Advances,2015,vol. 5,p. 57968 - 57974

34
[ 88-89-1 ]
[ 33529-01-0 ]
[ 1361182-31-1 ]

Reference： [1]New Journal of Chemistry,2012,vol. 36,p. 702 - 722

35
[ 33529-01-0 ]
[ 1361182-21-9 ]

Reference： [1]New Journal of Chemistry,2012,vol. 36,p. 702 - 722

36
[ 288-32-4 ]
[ 110-53-2 ]
[ 33529-01-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate; In acetone;Reflux;	General procedure: Briefly, a mixture of imidazole (100 mmol), alkyl bromide (100 mmol) and K2CO3 (200 mmol) inacetone (200 mL) was refluxed overnight. Upon filtration and solvent removal, the remaining residuewas subjected to flash chromatography with ethyl acetate to produce >90% yield.
		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).

Reference： [1]Molecules,2018,vol. 23
[2]Dyes and Pigments,2013,vol. 96,p. 16 - 24,9

37
[ 3099-28-3 ]
[ 33529-01-0 ]
3,3'-(pyridine-2,6-diylbis(methylene))bis(1-hexyl-1H-imidazol-3-ium)dichloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In neat (no solvent); at 60℃; for 16h;Inert atmosphere; Schlenk technique; Green chemistry;	General procedure: A generic experimental procedure is described: N-substituted imidazoles 1-6 (1 mmol equivalent) and 2,6-bis(chloromethyl)pyridine 7 (0.5mmol equivalent for each compound, m.p 73-78 C; ALDRICH) were mixed together under inert condition in a 50 ml round bottom flask with gentle stirring. The temperature was then gently raised to 60 C; giving a molten substance that was allowed to continue stirring for 16 h at 60 C. The resultant grey or light brown crude solid was allowed to cool to room temperature and loaded onto a short plug of silica. Unreacted starting materials are rinsed-out with ethyl acetate while the salts were obtained (Rf value 0.01) as methanol (100%) eluents. Solvent is then removed under reduced pressure to yield pure imidazolium salts 8-13.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 6351 - 6353
[2]Dalton Transactions,2013,vol. 42,p. 351 - 354
[3]Chemistry - A European Journal,2015,vol. 21,p. 7540 - 7555

38
[ 3099-28-3 ]
[ 33529-01-0 ]
C₂₅H₃₇Ag₂Cl₂N₅ [ No CAS ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 351 - 354
[2]Chemistry - A European Journal,2015,vol. 21,p. 7540 - 7555

39
[ 33529-01-0 ]
2C₁₅H₂₉N₂⁽¹⁺⁾*Br₂Cl₂Pd^(2-) [ No CAS ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 1385 - 1393

40
[ 33529-01-0 ]
[ 7338-94-5 ]
[ 1431720-85-2 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 2322 - 2324

41
[ 96-32-2 ]
[ 33529-01-0 ]
[ 1426824-46-5 ]

Reference： [1]Inorganic Chemistry,2017,vol. 56,p. 7558 - 7565
[2]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 423 - 427

42
[ 33529-01-0 ]
C₁₁H₂₃N₂O₇P₂⁽¹⁺⁾ [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 423 - 427

43
[ 33529-01-0 ]
[ 1309877-53-9 ]

Reference： [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 423 - 427
[2]Inorganic Chemistry,2017,vol. 56,p. 7558 - 7565

44
[ 34162-79-3 ]
[ 33529-01-0 ]
[ 1426824-32-9 ]

Reference： [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 423 - 427

45
[ 89889-20-3 ]
[ 33529-01-0 ]
[ 1258271-79-2 ]

Reference： [1]Journal of Materials Chemistry A,2013,vol. 1,p. 6572 - 6578

46
[ 2043-53-0 ]
[ 33529-01-0 ]
[ 1258271-80-5 ]

Reference： [1]Journal of Materials Chemistry A,2013,vol. 1,p. 6572 - 6578

47
[ 629-04-9 ]
[ 33529-01-0 ]
[ 1439629-16-9 ]

Reference： [1]Crystal Growth and Design,2013,vol. 13,p. 3068 - 3077

48
[ 544-10-5 ]
[ 33529-01-0 ]
1,3-dihexyl-1H-imidazol-3-ium chloride [ No CAS ]

Reference： [1]Journal of the Chinese Chemical Society,2013,vol. 60,p. 745 - 754

49
[ 3296-90-0 ]
[ 33529-01-0 ]
C₂₃H₄₂N₄O₂⁽²⁺⁾*2Br^(1-) [ No CAS ]

Reference： [1]Chinese Journal of Chemistry,2013,vol. 31,p. 1250 - 1256

50
[ 3296-90-0 ]
[ 33529-01-0 ]
2,2-bis((1-hexyl-1H-imidazol-3-yl-3-ium)methyl)propane-1,3-diol hexafluorophosphate [ No CAS ]

Reference： [1]Chinese Journal of Chemistry,2013,vol. 31,p. 1250 - 1256

51
[ 7697-37-2 ]
[ 33529-01-0 ]
[ 20667-12-3 ]
[ 1472103-63-1 ]

Reference： [1]Physical Chemistry Chemical Physics,2013,vol. 15,p. 18934 - 18943

52
[ 13483-18-6 ]
[ 33529-01-0 ]
C₂₂H₄₀N₄O₂⁽²⁺⁾*2Cl^(1-) [ No CAS ]

Reference： [1]Chemical Biology and Drug Design,2014,vol. 83,p. 278 - 288

53
[ 138418-40-3 ]
[ 33529-01-0 ]
C₂₃H₄₂N₄O₂⁽²⁺⁾*2Cl^(1-) [ No CAS ]

Reference： [1]Chemical Biology and Drug Design,2014,vol. 83,p. 278 - 288

54
[ 13483-19-7 ]
[ 33529-01-0 ]
C₂₄H₄₄N₄O₂⁽²⁺⁾*2Cl^(1-) [ No CAS ]

Reference： [1]Chemical Biology and Drug Design,2014,vol. 83,p. 278 - 288

55
[ 7093-33-6 ]
[ 33529-01-0 ]
C₂₅H₄₆N₄O₂⁽²⁺⁾*2Cl^(1-) [ No CAS ]

Reference： [1]Chemical Biology and Drug Design,2014,vol. 83,p. 278 - 288

56
[ 56894-92-9 ]
[ 33529-01-0 ]
C₂₆H₄₈N₄O₂⁽²⁺⁾*2Cl^(1-) [ No CAS ]

Reference： [1]Chemical Biology and Drug Design,2014,vol. 83,p. 278 - 288

57
[ 623-24-5 ]
[ 33529-01-0 ]
C₂₆H₄₀N₄⁽²⁺⁾*2F₆P^(1-) [ No CAS ]

Reference： [1]Inorganic Chemistry Communications,2014,vol. 47,p. 56 - 59

58
[ 1200-03-9 ]
[ 33529-01-0 ]
1-hexyl-3-(4-phenoxybutyl)-1H-imidazol-3-ium bromide [ No CAS ]