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Chemical Structure| 65039-08-9

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Product Details of [ 65039-08-9 ]

CAS No. :65039-08-9
Formula : C6H11BrN2
M.W : 191.07
SMILES Code : CN1C=C[N+](CC)=C1.[Br-]
MDL No. :MFCD03427610
InChI Key :GWQYPLXGJIXMMV-UHFFFAOYSA-M
Pubchem ID :2734235

Safety of [ 65039-08-9 ]

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

Computational Chemistry of [ 65039-08-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 5
Fraction Csp3 0.5
Num. rotatable bonds 1
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 43.02
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

8.81 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

-2.76
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.41
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-2.66
Log Po/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.

0.84
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.26
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.58

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.26
Solubility 1.05 mg/ml ; 0.00552 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.

-1.2
Solubility 12.1 mg/ml ; 0.0632 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.71
Solubility 37.6 mg/ml ; 0.197 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

Low
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.46 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

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.43

Application In Synthesis of [ 65039-08-9 ]

* 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 [ 65039-08-9 ]

[ 65039-08-9 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 65039-08-9 ]
  • [ 90076-65-6 ]
  • [ 174899-82-2 ]
YieldReaction ConditionsOperation in experiment
87.1% In water; at 60℃; for 2h; 2. Put 200g lithium bistrifluoromethylsulfonimide, 152g 1-ethyl-3-methylimidazole bromide salt and 400g pure water into the reactor,Warm to 60 , react for 2h,After standing for a while, 283 g of crude 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide salt was obtained. 3. Wash three times with pure water to obtain 251g of pure 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide salt.Distill it on a rotary evaporator under reduced pressure for 2h,Keep the temperature at 80 , remove most of the water,Finally, it is dried in a vacuum oven at 110 C for 12h.237 g of 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide was obtained. The purity of the product detected by liquid chromatography was 99.23%, and the yield was 87.1%;Ion chromatography detection: halogen ion 450ppm;ICP detection: Fe ion <1ppm, Pb ion <1ppm.
86% In water; at 20℃; for 2h;Heating / reflux; 9.40 g of methylimidazole (0.115 mol) in 50 ml of ethyl acetate is introduced into a 500 ml three-necked flask equipped with a condenser. 14.25 g of ethyl bromide (0.126 mol) is added dropwise at ambient temperature. Then, the mixture is left for two hours under reflux before being extracted by three times 25 ml of ethyl acetate. The product is dried under vacuum at 70 C. for thirty minutes; this is ethylmethylimidazolium bromide. NMR 1H: (200 MHz, CD3CN): delta 9.42 (t, 1H, Ha); 7.63 (d, 1H, Hb); 7.55 (d, 1H, Hc); 3.93 (s, 3H, Hd); 4.28 (q, 2H, He); 1.50 (t, 3H, Hf) This product is added dropwise at ambient temperature to a mixture containing 50 ml of water and 31.37 g of lithium bis(trifluorosulphonyl)imide (0.109 mol). Then the mixture is stirred for two hours under reflux. The product is then extracted with three times 20 ml of dichloromethane before being evaporated under vacuum at 70 C. for 30 minutes. The overall yield is 86%. NMR 1H: (200 MHz, CD3CN): delta 8.46 (s, 1H, Ha); 7.42 (s, 1H, Hb); 7.37 (s, 1H, Hc); 3.93 (s, 3H, Hd); 4.28 (q, 2H, He); 1.50 (t, 3H, Hf)
In water; at 70℃; for 24h;pH 6.0; General procedure: The respective halide IL was dissolved in deionized water (pH =6) and after an equimolar amount of LiNTf2 in water had been added dropwise, the reaction mixture was stirred for 1 day at 70 C. Then CH2Cl2 was added and the aqueous phase was removed. The organic phase was washed halide-free with deionized water (AgNO3 test). The solution was filtered over a column filled with neutral Al2O3 and activated charcoal. The organic solvent was removed under reduced pressure and the reaction product finally dried under dynamic vacuum for 1-2 days at 80-90 C.
383.5 g In water; Step 1: Take 287.1g of lithium bis (trifluoromethanesulfonyl) imide (LiTFSI) completely dissolved in water to form an aqueous solution with a mass percentage concentration of 50%; Step 2: 191.1 g of 1-ethyl-3-methylimidazolium bromide (EMIBr) was completely dissolved in water to form an aqueous solution having a mass percentage concentration of 50% Step 3: mixing the aqueous solution products obtained in steps 1 and 2 to obtain a crude product; Step 4: The crude product is obtained in step 3, washed with water for 2 times, emulsified by heating and stirring, and heated to 60 DEG C for demulsification, and then high purity product is obtained after liquid separation; Step 5: The high-purity product obtained in Step 4 was vacuum-dried at 100 C for 8 hours to obtain 383.5 g of colorless liquid EMI · TFSI product (melting point: about -15 C), purity: 99.95%, water content: 80 ppm, .

References: [1]Inorganic Chemistry,2018,vol. 57,p. 2314 - 2319.
[2]Organic and Biomolecular Chemistry,2008,vol. 6,p. 2522 - 2529.
[3]Organic Letters,2009,vol. 11,p. 1523 - 1526.
[4]Chemical Communications,2010,vol. 46,p. 1488 - 1490.
[5]Molecules,2011,vol. 16,p. 5963 - 5974.
[6]Angewandte Chemie - International Edition,2012,vol. 51,p. 11483 - 11486.
    Angew. Chem.,2012,vol. 124,p. 11650 - 11654,5.
[7]Organic and Biomolecular Chemistry,2013,vol. 11,p. 2534 - 2542.
[8]Patent: CN110878053,2020,A .Location in patent: Paragraph 0064; 0066.
[9]Patent: US2007/7137,2007,A1 .Location in patent: Page/Page column 4.
[10]Chemical Communications,2017,vol. 53,p. 11154 - 11156.
[11]Chemical Communications,2008,p. 4939 - 4941.
[12]Analytical Chemistry,2004,vol. 76,p. 2773 - 2779.
[13]Journal of the American Chemical Society,2005,vol. 127,p. 4976 - 4983.
[14]Journal of Materials Chemistry,2006,vol. 16,p. 1475 - 1482.
[15]Chemical Communications,2007,p. 2732 - 2734.
[16]Electrochimica Acta,2010,vol. 55,p. 7145 - 7151.
[17]Journal of Chemical and Engineering Data,2012,vol. 57,p. 875 - 881.
[18]Science China Chemistry,2012,vol. 55,p. 1519 - 1524.
[19]Journal of Molecular Liquids,2013,vol. 177,p. 361 - 368.
[20]Inorganic Chemistry,2013,vol. 52,p. 13167 - 13178.
[21]Dalton Transactions,2014,vol. 43,p. 568 - 575.
[22]Macromolecules,2013,vol. 46,p. 9464 - 9472.
[23]Journal of Molecular Liquids,2014,vol. 192,p. 191 - 198.
[24]Physical Chemistry Chemical Physics,2014,vol. 16,p. 23233 - 23243.
[25]Dalton Transactions,2016,vol. 45,p. 10151 - 10154.
[26]Patent: CN105985277,2016,A .Location in patent: Paragraph 0029; 0030; 0031; 0032; 0033; 0034.
[27]Journal of Chemical and Engineering Data,2018,vol. 63,p. 4484 - 4496.
  • 2
  • [ 554-95-0 ]
  • [ 6147-53-1 ]
  • [ 65039-08-9 ]
  • [ 174899-82-2 ]
  • [ 951026-20-3 ]
  • 3
  • [ 376-73-8 ]
  • [ 6147-53-1 ]
  • [ 65039-08-9 ]
  • [ 174899-82-2 ]
  • [1-ethyl-3-methylimidazolium]2[Co3(H2O)4(hexafluoroglutarate)4] [ No CAS ]
  • 4
  • [ 377-38-8 ]
  • [ 6147-53-1 ]
  • [ 65039-08-9 ]
  • [ 174899-82-2 ]
  • [1-ethyl-3-methylimidazolium]2[Co(H2O)2(tetrafluorosuccinate)2] [ No CAS ]
 

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