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[ CAS No. 36443-80-8 ] {[proInfo.proName]}

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Chemical Structure| 36443-80-8
Chemical Structure| 36443-80-8
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Product Details of [ 36443-80-8 ]

CAS No. :36443-80-8 MDL No. :MFCD07784451
Formula : C11H13ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :FCRZSGZCOGHOGF-UHFFFAOYSA-M
M.W : 208.69 Pubchem ID :10560335
Synonyms :

Calculated chemistry of [ 36443-80-8 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.18
Num. rotatable bonds : 2
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 59.63
TPSA : 8.81 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : -3.28
Log Po/w (XLOGP3) : 2.54
Log Po/w (WLOGP) : -1.64
Log Po/w (MLOGP) : 1.93
Log Po/w (SILICOS-IT) : 1.51
Consensus Log Po/w : 0.21

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.18
Solubility : 0.137 mg/ml ; 0.000655 mol/l
Class : Soluble
Log S (Ali) : -2.37
Solubility : 0.886 mg/ml ; 0.00425 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.89
Solubility : 0.268 mg/ml ; 0.00128 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.44

Safety of [ 36443-80-8 ]

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 [ 36443-80-8 ]

* 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 [ 36443-80-8 ]

[ 36443-80-8 ] Synthesis Path-Downstream   1~59

  • 1
  • [ 616-47-7 ]
  • [ 100-44-7 ]
  • [ 36443-80-8 ]
YieldReaction ConditionsOperation in experiment
99% at 100℃; Microwave irradiation;
95% In toluene for 72h; Heating;
95% In acetonitrile for 48h; Inert atmosphere; Reflux;
95% In toluene at -0.16 - 69.84℃; for 32.5h;
94% In neat (no solvent) for 2h; Milling;
91% Heating;
90% In tetrahydrofuran for 24h; Schlenk technique; Reflux;
86% With potassium carbonate In acetonitrile at 70℃; for 72h;
84% In tetrahydrofuran Reflux;
78% at 40 - 110℃; for 5h; Benzyl chloride (0.4 mol) was dropped into methylimidazole (0.4 mol), stirred at 40 °C. The mixture was stirred for 5 h at 70-110 °C. The obtained crude 1-benzyl-3-methylimidazolium chloride, [Bzlmim]Cl, in the form of a light-orange viscous oil was dissolved in 70 cm3 acetonitrile and washed with diethyl ether (3 × 40 cm3), ethyl acetate (4 × 20 cm3), and again with diethyl ether (4 × 50 cm3), and finally with hexane (4 × 50 cm3). The product was left to stand over the hexane phase overnight to crystallize. The solid form was dried by nitrogen flow in a Schlenk apparatus to reach a constant weight. The product was obtained in the form of an off-white powder with 78% yield.
at 80℃; for 72h;
In acetonitrile at 24.84℃;
In toluene
In toluene
at 150℃; for 0.5h; Microwave irradiation; Cooling; neat (no solvent);
In toluene at 109.84℃; for 24h;
In toluene for 24h; Reflux;
In toluene for 24h; Reflux;
In toluene
In toluene for 24h; Reflux;
In toluene at 80℃; for 24h;
With sodium iodide In acetone at 20℃; for 12h; Schlenk technique;
In chloroform at 20℃; for 5h; 13.1 (1) Synthesis of Intermediate (b) Example 13 Synthesis of Compound B-13 (1) Synthesis of Intermediate (b) In 100 g of chloroform, 30 g of benzyl chloride was dissolved, and to this, 20 g of 1-methylimidazole was added dropwise. The contents were stirred at room temperature. After 5 hours, the disappearance of the raw materials was confirmed by HPLC, and a 50% chloroform solution of Intermediate (b) was obtained.
at 80℃; for 3h; Sealed tube;

Reference: [1]Erdmenger, Tina; Vitz, Juergen; Wiesbrock, Frank; Schubert, Ulrich S. [Journal of Materials Chemistry, 2008, vol. 18, # 43, p. 5267 - 5273]
[2]Brenna, Stefano; Posset, Tobias; Furrer, Julien; Bluemel, Janet [Chemistry - A European Journal, 2006, vol. 12, # 10, p. 2880 - 2888]
[3]Location in patent: experimental part Kilpelaeinen, Ilkka; Xie, Haibo; King, Alistair; Granstrom, Mari; Heikkinen, Sami; Argyropoulos, Dimitris S. [Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 22, p. 9142 - 9148]
[4]Location in patent: experimental part Srivastava, Rajendra [Catalysis Letters, 2010, vol. 139, # 1-2, p. 17 - 25]
[5]Beillard, Audrey; Golliard, Ethan; Gillet, Valentin; Bantreil, Xavier; Métro, Thomas-Xavier; Martinez, Jean; Lamaty, Frédéric [Chemistry - A European Journal, 2015, vol. 21, # 49, p. 17614 - 17617]
[6]Location in patent: experimental part Zhuravlev; Verolainen; Voronchikhina [Russian Journal of Applied Chemistry, 2011, vol. 84, # 7, p. 1158 - 1164]
[7]Tang, Xiaodong; Qi, Chaorong; He, Haitao; Jiang, Huanfeng; Ren, Yanwei; Yuan, Gaoqing [Advanced Synthesis and Catalysis, 2013, vol. 355, # 10, p. 2019 - 2028]
[8]Rehm, Tobias; Rothemund, Matthias; Muenzner, Julienne K.; Noor, Awal; Kempe, Rhett; Schobert, Rainer [Dalton Transactions, 2016, vol. 45, # 39, p. 15390 - 15398]
[9]Lima, Heather M.; Lovely, Carl J. [Organic Letters, 2011, vol. 13, # 21, p. 5736 - 5739]
[10]Ochȩdzan-Siodłak, Wioletta; Dziubek, Katarzyna; Siodłak, Dawid [Journal of Molecular Liquids, 2013, vol. 177, p. 85 - 93]
[11]Day, Graeme; Glaser, Rainer; Shimomura, Noriyuki; Takamuku, Atsushi; Ichikawa, Kazuhiko [Chemistry - A European Journal, 2000, vol. 6, # 6, p. 1078 - 1086]
[12]Letaief, Sadok; Detellier, Christian [Journal of Materials Chemistry, 2007, vol. 17, # 15, p. 1476 - 1484]
[13]Location in patent: experimental part Bini, Riccardo; Chiappe, Cinzia; Pomelli, Christian Silvio; Parisi, Benedetta [Journal of Organic Chemistry, 2009, vol. 74, # 22, p. 8522 - 8530]
[14]Location in patent: scheme or table Kore, Rajkumar; Srivastava, Rajendra [Journal of Molecular Catalysis A: Chemical, 2011, vol. 345, # 1-2, p. 117 - 126]
[15]Location in patent: scheme or table Li, Xinzhong; Lin, Qi; Ma, Liang [Ultrasonics Sonochemistry, 2010, vol. 17, # 5, p. 752 - 755] Location in patent: scheme or table Kore, Rajkumar; Srivastava, Rajendra [Catalysis Communications, 2011, vol. 12, # 15, p. 1420 - 1424]
[16]Location in patent: experimental part Ceron, Miguel A.; Guzman-Lucero, Diego J.; Palomeque, Jorge F.; Martinez-Palou, Rafael [Combinatorial Chemistry and High Throughput Screening, 2012, vol. 15, # 5, p. 427 - 432]
[17]Location in patent: scheme or table Kore, Rajkumar; Srivastava, Rajendra [Tetrahedron Letters, 2012, vol. 53, # 26, p. 3245 - 3249]
[18]Location in patent: scheme or table Kore, Rajkumar; Kumar, T.J. Dhilip; Srivastava, Rajendra [Journal of Molecular Catalysis A: Chemical, 2012, vol. 360, p. 61 - 70]
[19]Kore, Rajkumar; Tumma, Mahesh; Srivastava, Rajendra [Catalysis Today, 2012, vol. 198, # 1, p. 189 - 196]
[20]Ravindran, Anaswara; Kore, Rajkumar; Srivastava, Rajendra [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 1, p. 129 - 135]
[21]Kore, Rajkumar; Srivastava, Rajendra [Journal of Molecular Catalysis A: Chemical, 2013, vol. 376, p. 90 - 97]
[22]Wang, Jinquan; Sng, Waihong; Yi, Guangshun; Zhang, Yugen [Chemical Communications, 2015, vol. 51, # 60, p. 12076 - 12079]
[23]Banerjee, Mainak; Karri, Ramesh; Rawat, Kuber Singh; Muthuvel, Karthick; Pathak, Biswarup; Roy, Gouriprasanna [Angewandte Chemie - International Edition, 2015, vol. 54, # 32, p. 9323 - 9327][Angew. Chem., 2015, vol. 127, p. 9455 - 9459,5]
[24]Current Patent Assignee: SANYO CHEMICAL INDUSTRIES LTD; EVONIK INDUSTRIES AG - US2016/9737, 2016, A1 Location in patent: Paragraph 0109
[25]Pellerite, Mark J.; Kaplun, Marina M.; Webb, Robert J. [Journal of Organic Chemistry, 2019, vol. 84, # 23, p. 15486 - 15497]
  • 2
  • [ 1934-75-4 ]
  • [ 36443-80-8 ]
  • 1-benzyl-3-methylimidazolium dicyanoamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% In water at 20℃; for 12h; Inert atmosphere;
  • 3
  • [ 12107-56-1 ]
  • [ 918824-07-4 ]
  • [ 36443-80-8 ]
  • [Pd(1-(methyl)-3-(benzyl)imidazol-2-ylidene)2Cl2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% In dichloromethane under Ar, in absence of light; mixt. of imidazolium salt and AgOC(CF3)3 in CH2Cl2 stirred at room temp. for 2 h; Pd complex added; stirred at room temp. for 2 h; soln. column chromd. (silica gel, acetone (5%)-CH2Cl2);
  • 4
  • [(η5-pentamethylcyclopentadienyl)iridium(III)dichloride]2 [ No CAS ]
  • [ 918824-07-4 ]
  • [ 7681-82-5 ]
  • [ 36443-80-8 ]
  • (C5Me5)Ir[1-(methyl)-3-(benzyl)imidazol-2-ylidene]I2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% In acetonitrile under Ar, in absence of light; mixt. of imidazolium salt and AgOC(CF3)3 in MeCN stirred at room temp. for 2 h; Ir complex and NaI added; heated at 60°C and stirred for 5 h; cooled to room temp.; filtered through Celite; solvent removed under vac.; purified by column chromy. (silica gel, acetone (2%)-heptane);
  • 5
  • [ 29892-37-3 ]
  • [ 918824-07-4 ]
  • [ 36443-80-8 ]
  • ([1-benzyl-3-methyl]imidazolyl-2-ene)gold chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% In dichloromethane under Ar, in absence of light; mixt. of imidazolium salt and AgOC(CF3)3 in CH2Cl2 stirred at room temp. for 2 h; Au complex added; stirred for 2h; cooled to room temp.; filtered through Celite; solvent removed under vac.; purified by column chromy. (silica gel, CH2Cl2);
  • 6
  • [ 918824-07-4 ]
  • [ 36443-80-8 ]
  • ([1-benzyl-3-methyl]imidazolyl-2-ene)silver chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% In acetonitrile under Ar, in absence of light; mixt. of imidazolium salt and AgOC(CF3)3 in MeCN stirred at room temp. for 2 h; soln. filtered through Celite; solvent removed under vac.; repptd. from CH2Cl2-ether;
  • 7
  • dichloro(p-cymene)ruthenium(II) dimer [ No CAS ]
  • [ 918824-07-4 ]
  • [ 36443-80-8 ]
  • dichloro(η6-p-cymene)(3-methyl-1-benzylimidazol-2-ylidene)ruthenium(II) [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% In dichloromethane under Ar, in absence of light; mixt. of imidazolium salt and AgOC(CF3)3 in CH2Cl2 stirred at room temp. for 2 h; soln. of Ru complex in CH2Cl2 added; stirred at room temp. for 2 h; solvent removed under vac.; purified by column chromy. (silica gel, acetone (20%)-pentane);
  • 8
  • [ 36443-80-8 ]
  • [ 500996-04-3 ]
  • 9
  • [ 36443-80-8 ]
  • C11H13N2O3S(1+)*H3O4S(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With sulfuric acid at -3.16 - 69.84℃; for 12h;
  • 10
  • bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] [ No CAS ]
  • [ 7681-82-5 ]
  • [ 36443-80-8 ]
  • (C5Me5)Ir[1-(methyl)-3-(benzyl)imidazol-2-ylidene]I2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With Ag(OC(CF3)3) In acetonitrile mixt. of Ag compd. (0.37 mmol) and ligand (0.25 mmol) in MeCN stirred atroom temp. for 2 h, Ir compd. (0.13 mmol) ans NaI (1 mmol) added, mixt. heated to 60°C for 5 h; cooled, filtered, evapd. (vac.), chromd. (SiO2, 2% acetone/heptane), elem. anal.;
  • 11
  • [ 3459-92-5 ]
  • [ 35487-17-3 ]
  • [ 36443-80-8 ]
YieldReaction ConditionsOperation in experiment
> 99 %Spectr. at 169.84℃; for 8h; Autoclave; Neat (no solvent);
  • 12
  • Al2Si2O5(OH)4*0.75(CH3)2SO [ No CAS ]
  • [ 36443-80-8 ]
  • Al2Si2O5(OH)4*0.58C6H5CH2NC3H3NCH3(1+)*0.58Cl(1-)=Al2Si2O5(OH)4*0.58(C6H5CH2NC3H3NCH3)Cl [ No CAS ]
YieldReaction ConditionsOperation in experiment
In melt chloride was added to Al compd. at room temp.; heated under flow of N2; heated to 180°C and stirred for 2 h; washed-centrifuged with isopropanol; dried at 60°C overnight; ground;
  • 14
  • [ 36443-80-8 ]
  • [ 956597-95-8 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid
  • 15
  • [ 1274452-24-2 ]
  • [ 36443-80-8 ]
  • [ 1331734-75-8 ]
YieldReaction ConditionsOperation in experiment
1.17 g In acetone at 20℃; Sonication;
  • 17
  • [ 769069-45-6 ]
  • [ 36443-80-8 ]
  • 1-benzyl-2-tert-butoxycarbonylimino-2,3-dihydro-3-methyl-1H-imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.15 g With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0 - 20℃;
  • 18
  • [ 30830-47-8 ]
  • [ 36443-80-8 ]
  • 1-benzyl-2-benzyloxycarbonylimino-2,3-dihydro-3-methyl-1H-imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.082 g With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0 - 20℃;
  • 19
  • [ 36443-80-8 ]
  • 3-benzyl-1-methyl-1,3-dihydro-2H-imidazol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With sodium hypochlorite; sodium hydroxide In tetrahydrofuran at 20℃; for 0.166667h;
  • 20
  • iron(III) chloride hexahydrate [ No CAS ]
  • [ 36443-80-8 ]
  • [ 1334246-38-6 ]
YieldReaction ConditionsOperation in experiment
In ethanol ionic liquid prepd. by mixing hot ethanolic solns. of FeCl3*6H2O and imidazolium chloride; mixt. heated with stirring for 10-15 min; ethanol evapd. under vac.; ionic liquid washed with cold dry ether and dried under vac. over P2O5 for d; elem. anal.;
  • 21
  • [ 36443-80-8 ]
  • [ 1379371-68-2 ]
YieldReaction ConditionsOperation in experiment
81% With chlorosulfonic acid In dichloromethane at 69.84℃; for 12h;
With chlorosulfonic acid
  • 22
  • [ 36443-80-8 ]
  • [ 1380315-11-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloromethane 2: chlorosulfonic acid / dichloromethane
  • 23
  • [ 36443-80-8 ]
  • [ 1380315-12-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloromethane 2: chlorosulfonic acid / dichloromethane
  • 24
  • [ 104-15-4 ]
  • [ 36443-80-8 ]
  • 1-benzyl-3-methylimidazolium p-toluenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% In dichloromethane
  • 25
  • [ 76-05-1 ]
  • [ 36443-80-8 ]
  • 1-benzyl-3-methylimidazolium trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% In dichloromethane
  • 26
  • palladium dichloride [ No CAS ]
  • [ 36443-80-8 ]
  • [Pd(1-(methyl)-3-(benzyl)imidazol-2-ylidene)2Cl2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile for 24h; Inert atmosphere; Reflux;
  • 27
  • [ 7646-85-7 ]
  • [ 36443-80-8 ]
  • C11H13N2(1+)*Cl(1-)*2ZnCl2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 149.84℃; for 4h;
  • 28
  • aluminum (III) chloride [ No CAS ]
  • [ 36443-80-8 ]
  • [ 1391982-11-8 ]
YieldReaction ConditionsOperation in experiment
To the obtained [Bzlmim]Cl an equivalent amount of aluminium chloride was added slowly while the mixture was constantly stirred. The obtained 1-benzyl-3-methylimidazolium chloroaluminate, liquid during synthesis, crystallized in the form of an off-white solid.
  • 29
  • [ 20667-12-3 ]
  • [ 36443-80-8 ]
  • ([1-benzyl-3-methyl]imidazolyl-2-ene)silver chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% In neat (no solvent) for 0.166667h; Milling;
In dichloromethane for 12h; Reflux;
  • 30
  • [ 36443-80-8 ]
  • C22H24N4Se2(2+)*2I(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; selenium / methanol / 24 h / Schlenk technique; Reflux 2: iodine / dichloromethane / 3 h / 0 - 20 °C / Schlenk technique; Inert atmosphere
  • 31
  • [ 36443-80-8 ]
  • C11H12IN2Se(1+)*I(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; selenium / methanol / 24 h / Schlenk technique; Reflux 2: lactoperoxidase; dihydrogen peroxide; potassium iodide / methanol; aq. phosphate buffer / 20 °C / pH 7.4 / Enzymatic reaction
  • 32
  • [ 36443-80-8 ]
  • [ 23269-08-1 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; sulfur In methanol for 24h; Schlenk technique; Reflux;
With potassium carbonate; sulfur In methanol for 24h; Reflux; Schlenk technique;
  • 33
  • [ 36443-80-8 ]
  • [ 920519-25-1 ]
YieldReaction ConditionsOperation in experiment
With selenium; potassium carbonate In methanol for 24h; Schlenk technique; Reflux;
With selenium; potassium carbonate In methanol for 24h; Reflux; Schlenk technique;
  • 34
  • [ 36443-80-8 ]
  • C11H12N2S*CH3Hg(1+)*HO(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; sulfur / methanol / 24 h / Reflux; Schlenk technique 2: 360 h / 35 °C / Schlenk technique
  • 35
  • [ 36443-80-8 ]
  • C11H12N2S*CH3Hg(1+)*Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; sulfur / methanol / 24 h / Reflux; Schlenk technique 2: 360 h / 35 °C / Schlenk technique
  • 36
  • [ 36443-80-8 ]
  • C11H12N2S*C2H5Hg(1+)*HO(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; sulfur / methanol / 24 h / Reflux; Schlenk technique 2: 360 h / 35 °C / Schlenk technique
  • 37
  • [ 36443-80-8 ]
  • C11H12N2S*C2H5Hg(1+)*Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; sulfur / methanol / 24 h / Reflux; Schlenk technique 2: 360 h / 35 °C / Schlenk technique
  • 38
  • [ 36443-80-8 ]
  • C11H12N2S*C6H5Hg(1+)*HO(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; sulfur / methanol / 24 h / Reflux; Schlenk technique 2: 360 h / 35 °C / Schlenk technique
  • 39
  • [ 36443-80-8 ]
  • C11H12N2S*C6H5Hg(1+)*Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; sulfur / methanol / 24 h / Reflux; Schlenk technique 2: 360 h / 35 °C / Schlenk technique
  • 40
  • [ 36443-80-8 ]
  • C11H12N2Se*CH3Hg(1+)*HO(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; selenium / methanol / 24 h / Reflux; Schlenk technique 2: 360 h / 35 °C / Schlenk technique
  • 41
  • [ 36443-80-8 ]
  • C11H12N2Se*CH3Hg(1+)*Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; selenium / methanol / 24 h / Reflux; Schlenk technique 2: 360 h / 35 °C / Schlenk technique
  • 42
  • [ 36443-80-8 ]
  • C11H12N2Se*C2H5Hg(1+)*HO(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; selenium / methanol / 24 h / Reflux; Schlenk technique 2: 360 h / 35 °C / Schlenk technique
  • 43
  • [ 36443-80-8 ]
  • C11H12N2Se*C2H5Hg(1+)*Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; selenium / methanol / 24 h / Reflux; Schlenk technique 2: 360 h / 35 °C / Schlenk technique
  • 44
  • [ 36443-80-8 ]
  • C11H12N2Se*C6H5Hg(1+)*HO(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; selenium / methanol / 24 h / Reflux; Schlenk technique 2: 360 h / 35 °C / Schlenk technique
  • 45
  • [ 36443-80-8 ]
  • C11H12N2Se*C6H5Hg(1+)*Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; selenium / methanol / 24 h / Reflux; Schlenk technique 2: 360 h / 35 °C / Schlenk technique
  • 46
  • [ 143-66-8 ]
  • [ 36443-80-8 ]
  • [ 1008762-57-9 ]
YieldReaction ConditionsOperation in experiment
In chloroform; water at 20℃; for 3h; 13.2 (2) Synthesis of Compound B-13 (2) Synthesis of Compound B-13 To 6.3 g of the 50% chloroform solution of Intermediate (b) obtained in (1), 6.1 g of sodium tetraphenylborate (available from NACALAI TESQUE, INC.) and 50 g of ion-exchanged water were added and stirred for 3 hours at room temperature. An organic layer was washed with 50 g of ion-exchanged water three times. The organic layer was concentrated and the solvent was evaporated, after which the residue was subjected to silica gel chromatography to obtain a white solid. It was confirmed by 1H-NMR that this white solid was Compound B-13. The structure of Compound B-13 was described in Table 1.
  • 47
  • [ 12112-67-3 ]
  • [ 36443-80-8 ]
  • C16H24Cl4Ir2(2-)*2C11H13N2(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane Schlenk technique; Inert atmosphere;
  • 48
  • cis-[dichlorido-(1,3-dibenzylimidazol-2-ylidene)(dimethylsufoxide)]platinum(II) [ No CAS ]
  • [ 36443-80-8 ]
  • cis-[dichlorido-(1,3-dibenzylimidazol-2-ylidene)(1-benzyl-3-methylimidazol-2-ylidene)]platinum(II) [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With potassium <i>tert</i>-butylate In dichloromethane at 20℃; for 16h;
  • 49
  • [ 36443-80-8 ]
  • 2C11H13N2(1+)*Sn3Se7(2-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
11.5% With selenium; hydrazine hydrate; sodium stannate trihydrate at 150℃; for 144h; Autoclave; For the synthesis of 2: A mixture of Na2SnO3·3H2O (0.267g, 1mmol), Se powder (0.198g, 2.5mmol) and 0.200mL en in 1g [Bzmim]Cl was sealed in a 20mL Teflon-lined stainless-steel autoclave at 150°C for 6days, followed by slowly cooling to room temperature under a cooling rate of ~5.4Kh-1. The product was washed with N,N-dimethylformamideand ethanol for several times. Red block-like crystals of 2 were obtained by manually selection (Yield: 0.048g, 11.5% based on Sn). Elemental analysis: calcd. (%) for C22H26N4Se7Sn3: C 21.05, H 2.09, N 4.46; found: C 20.37, H 2.13, N 4.45.
  • 50
  • [ 5165-97-9 ]
  • [ 36443-80-8 ]
  • 1-benzyl-3-methylimidazolium 2-acrylamido-2-methyl-1-propanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetone at 20℃; for 48h; Inert atmosphere;
In acetone at 20℃; for 96h; Inert atmosphere; 2.2. Synthetic protocol for ILs General procedure: ILswere synthesized by procedure described earlier [28]. 0.5 molof chloride-based reactant IL (1-ethyl-3-methylimidazolium, Nbutylpyridinium,1-benzyl-3-methylimidazolium, 1-butyl-3-methylimidazolium, 1-butyl-1methylpyrrolidinium, morpholiniumand (vinylbenzyl)trimethylammonium) was taken in round bottomflask and 25 mL of acetone was further poured inside. Then 0.5 molof Na-salt of 2-acrylamido-2-methyl-1-propanesulfonic acid wastransferred to reaction mixture. The resultant mixture wasmagnetically stirred at ambient temperature under inert atmospherefor 4 days. The vacuum filtration of the mixture was doneand solvent in the filtrate was evaporated. The respective ILs obtainedafter evaporation of solvent were dissolved in DCM andextracted thrice with 10mL of cold water to get rid of traces of NaClissued from metathesis reaction.
  • 51
  • [ 36443-80-8 ]
  • [1-benzyl-3-methylimidazolium]2TeCl6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With tellurium tetrachloride In acetonitrile at 120℃; for 96h; Autoclave;
  • 52
  • [ 68474-35-1 ]
  • [ 36443-80-8 ]
  • [PdCl2(1-benzyl-3-methylimidazol-2-ylidene)(1-methylimidazole)] [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With potassium carbonate In tetrahydrofuran; acetonitrile at 50℃; for 24h; 2.3. Synthesis of palladium PEPPSI-type complexes with differentcarbene ligands [PdCl2(NHC)(imidazole)]. Method B General procedure: Palladium (II) complex with 1-methylimidazole ligands[PdCl2(1-methylimidazole)2] (0.5 mmol, 0.17 g), K2CO3 (1.5 mmol,0.21 g), MgSO4 (0.2 g, for drying), an appropriate imidazoliumchloride (0.65 mmol) and finally a mixture of solvents CH3CN:THF(8 ml: 5 ml) were placed in a round-bottom flask equipped with astirring bar. The flask was capped with a rubber septum. Themixture was heated in the oil bath for 24 h at 50 °C in the air atmosphere.During that time, the color changed from yellow togreenish. After the reaction, the cooled down mixture was filtratedto remove inorganic salts. Then, the yellow solutionwas evaporatedunder vacuum and the resulting oily residue was dissolved in aminimum amount of acetone. Next, 10 ml of water was slowlyadded to the yellow solution and clouding of the mixture wasobserved. The mixture was left to evaporate acetone and to enablesedimentation of the formed precipitate. After that time, waterwith excess of the imidazolium chloride and 1-methylimidazolewas decanted. The obtained product was washed with the waterand dried under vacuum. The complexes 2f and 2 g were obtainedfrom the appropriate imidazole and the precipitated solids requiredadditional washing with ethyl alcohol and diethyl ether. One of theobtained complexes [PdCl2(IMes)(1-methylimidazole)] (2e) wasdescribed in the literature [7b].
  • 53
  • copper(l) chloride [ No CAS ]
  • [ 36443-80-8 ]
  • C11H12ClCuN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: copper(l) chloride With sodium hexamethyldisilazane In tetrahydrofuran at 20℃; for 24h; Stage #2: 1-benzyl-3-methylimidazolium chloride In tetrahydrofuran; dichloromethane for 24h;
  • 56
  • [ 36443-80-8 ]
  • [ 71-47-6 ]
  • [ 666-14-8 ]
  • [ 74-89-5 ]
  • [ 100-46-9 ]
YieldReaction ConditionsOperation in experiment
1: 0.77 mol 2: 0.36 mol 3: 0.55 mol 4: 0.98 mol With potassium hydroxide In water at 60℃; for 264h;
YieldReaction ConditionsOperation in experiment
...cylimidazolium formate, 1-benzyl-3-(2-ethylhexyl)imidazolium formate, 1,3-didodecylimidazolium formate, 1-dodecyl-3-octadecylimidazolium formate, 1-benzyl-3-dodecylimidazolium formate, 1,3-dioctadecylimidazolium formate, 1-benzyl-3-octadecylimidazolium formate, 1,3-dibenzylimidazolium formate,1,3-dimethylimidazolium acetate, 1-ethyl-3-methylimidazolium acetate, 1-butyl-3-methylimidazolium acetate, 1-methyl-3-octylimidazolium acetate, 1-methyl-3-(2-ethylhexyl)imidazolium acetate, 1-dodecyl-3-methylimidazolium acetate, 1-methyl-3-octadecylimidazolium acetate, 1-benzyl-3-methylimidazolium acetate, 1,3-dibutylimidazolium acetate, 1-butyl-3-ethylimidazolium acetate, 1-butyl-3-octylimidazolium acetate, 1-butyl-3-(2-ethylhexyl)imidazolium acetate, 1-butyl-3-dodecylimidazolium acetate, 1-butyl-3-octadecylimidazclium acetate, 1-benzyl-3-butylimidazolium acetate, 1,3-dioctylimidazolium acetate, 1-ethyl-3-octylimidazolium acetate, 1-octyl-3-(2-ethylhexyl)imidazolium acetate, 1-dodecyl-3-octylimidazolium acetate, 1-octyl-3-octadecylimidazolium acetate, 1-benzyl-3-octylimidazolium acetate, 1,3-bis(2-ethylhexyl)imidazolium acetate, 1-ethyl-3-(2-ethylhexyl)imidazolium acetate, 1-(2-ethylhexyl)-3-dodecylimidazolium acetate, 1-(2-ethylhexyl)-3-octadecylimidazolium acetate, 1-benzyl-3-(2-ethylhexyl)imidazolium acetate, 1,3-didodecylimidazolium acetate, 1-dodecyl-3-octadecylimidazolium acetate, 1-benzyl-3-dodecylimidazolium acetate, 1,3-dioctadecylimidazolium acetate, 1-benzyl-3-octadecylimidazolium acetate, 1,3-dibenzylimidazolium acetate, 1,3-dimethylimidazolium lactate, 1-ethyl-3-methylimidazolium lactate, 1-butyl-3-methylimidazolium lactate, 1-methyl-3-octylimidazolium lactate, 1-methyl-3-(2-ethylhexyl)imidazolium lactate, 1-dodecyl-3-methylimidazolium lactate, 1-methyl-3-octadecylimidazolium lactate, 1-benzyl-3-methylimidazolium lactate, 1,3-dibutylimidazolium lactate, 1-butyl-3-ethylimidazolium lactate, 1-butyl-3-octylimidazolium lactate, 1-butyl-3-(2-ethylhexyl)imidazolium lactate, 1-butyl-3-dodecylimidazolium lactate, 1-butyl-3-octadecylimidazolium lactate, 1-benzyl-3-butylimidazolium lactate, 1,3-dioctylimidazolium lactate, 1-ethyl-3-octylimidazolium lactate, 1-octyl-3-(2-ethylhexyl)imidazolium lactate, 1-dodecyl-3-octylimidazolium lactate, 1-octyl-3-octadecylimidazolium lactate, 1-benzyl-3-octylimidazolium lactate, 1,3-bis(2-ethylhexyl)imidazolium lactate, 1-ethyl-3-(2-ethylhexyl)imidazolium lactate, 1-(2-ethylhexyl)-3-dodecylimidazolium lactate, 1-(2-ethylhexyl)-3-octadecylimidazolium lactate, 1-benzyl-3-(2-ethylhexyl)imidazolium lactate, 1,3-didodecylimidazolium lactate, 1-dodecyl-3-octadecylimidazolium lactate, 1-benzyl-3-dodecylimidazolium lactate, 1,3-dioctadecylimidazolium lactate, 1-benzyl-3-octadecylimidazolium lactate, 1,3-dibenzylimidazolium lactate, 1,3-dimethylimidazolium hydrogen carbonate, 1-ethyl-3-methylimidazolium hydrogen carbonate, 1-butyl-3-methylimidazolium hydrogen carbonate, 1-methyl-3-octylimidazolium hydrogen carbonate, 1-methyl-3-(2-ethylhexyl)imidazolium hydrogen carbonate, 1-dodecyl-3-methylimidazolium hydrogen carbonate, 1-methyl-3-octadecylimidazolium hydrogen carbonate, 1-benzyl-3-methylimidazolium hydrogen carbonate, 1,3-dibutylimidazolium hydrogen carbonate, 1-butyl-3-ethylimidazolium hydrogen carbonate, 1-butyl-3-octylimidazolium hydrogen carbonate, 1-butyl-3-(2-ethylhexyl)imidazolium hydrogen carbonate, 1-butyl-3-dodecylimidazolium hydrogen carbonate, 1-butyl-3-octadecylimidazolium hydrogen carbonate, 1-benzyl-3-butylimidazolium hydrogen carbonate, 1,3-dioctylimidazolium hydrogen carbonate, 1-ethyl-3-octylimidazolium hydrogen carbonate, 1-octyl-3-(2-ethylhexyl)imidazolium hydrogen carbonate, 1-dodecyl-3-octylimidazolium hydrogen carbonate, 1-octyl-3-octadecylimidazolium hydrogen carbonate, 1-benzyl-3-octylimidazolium hydrogen carbonate, 1,3-bis(2-ethylhexyl)imidazolium hydrogen carbonate, 1-ethyl-3-(2-ethylhexyl)imidazolium hydrogen carbonate, 1-(2-ethylhexyl)-3-dodecylimidazolium hydrogen carbonate, 1-(2-ethylhexyl)-3-octadecylimidazolium hydrogen carbonate, 1-benzyl-3-(2-ethylhexyl)imidazolium hydrogen carbonate, 1,3-didodecylimidazolium hydrogen carbonate, 1-dodecyl-3-octadecylimidazolium hydrogen carbonate, 1-benzyl-3-dodecylimidazolium hydrogen carbonate, 1,3-dioctadecylimidazolium hydrogen carbonate, 1-benzyl-3-octadecylimidazolium hydrogen carbonate, 1,3-dibenzylimidazolium hydrogen carbonate, 1,3-dimethylimidazolium chloride, 1-ethyl-3-methylimidazolium chloride, 1-butyl-3-methylimidazolium chloride, 1-methyl-3-octylimidazolium chloride, 1-methyl-3-(2-ethylhexyl)imidazolium chloride, 1-dodecyl-3-methylimidazolium chloride, 1-methyl-3-octadecylimidazolium chloride, 1-benzyl-3-methylimidazolium chloride, 1,3-dibutylimidazolium chloride, 1-butyl-3-ethylimidazolium chloride, 1-butyl-3-octylimidazolium chloride, 1-butyl-3-(2-ethylhexyl)imidazolium chloride, 1-butyl-3-dodecylimidazolium chloride, 1-butyl-3-octadecylimidazolium chloride, 1-benzyl-3-butylimidazolium chloride, 1,3-dioctylimidazolium chloride, 1-ethyl-3-octylimidazolium chloride, 1-octyl-3-(2-ethylhexyl)imidazolium chloride, 1-dodecyl-3-octylimidazolium chloride, 1-octyl-3-octadecylimidazolium chloride, 1-benzyl-3-octylimidazolium chloride, 1,3-bis(2-ethylhexyl)imidazolium chloride, 1-ethyl-3-(2-ethylhexyl)imidazolium chloride, 1-(2-ethylhexyl)-3-dodecylimidazolium chloride, 1-(2-ethylhexyl)-3-octadecylimidazolium chloride, 1-benzyl-3-(2-ethylhexyl)imidazolium chloride, 1,3-didodecylimidazolium chloride, 1-dodecyl-3-octadecylimidazolium chloride, 1-benzyl-3-dodecylimidazolium chloride, 1,3-dioctadecylimidazolium chloride, 1-benzyl-3-octadecylimidazolium chloride, 1,3-dibenzylimidazolium chloride, 1,3-dimethylimidazolinium formate, 1,3-dimethylimidazolinium acetate, 1,3-dimethylimidazolinium lactate, 1,3-dimethylimidazolinium hydrogen carbonate, 1,3-dimethylimidazolinium chloride, 1-butyl-3-methylimidazolinium formate, 1-butyl-3-methylimidazolinium acetate, 1-butyl-3-methylimidazolinium lactate, 1-butyl-3-methylimidazolinium hydrogen carbonate, 1-butyl-3-methylimidazolinium chloride, 1-methyl-3-octylimidazolinium formate, 1-methyl-3-octylimidazolinium acetate, 1-methyl-3-octylimidazolinium lactate, 1-methyl-3-octylimidazolinium hydrogen carbonate, 1-methyl-3-octylimidazolinium chloride,
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