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Chemical Structure| 85100-77-2 Chemical Structure| 85100-77-2

Structure of 85100-77-2

Chemical Structure| 85100-77-2

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Product Details of [ 85100-77-2 ]

CAS No. :85100-77-2
Formula : C8H15BrN2
M.W : 219.12
SMILES Code : CN1C=C[N+](CCCC)=C1.[Br-]
MDL No. :MFCD03427611
InChI Key :KYCQOKLOSUBEJK-UHFFFAOYSA-M
Pubchem ID :2734236

Safety of [ 85100-77-2 ]

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

Computational Chemistry of [ 85100-77-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 5
Fraction Csp3 0.62
Num. rotatable bonds 3
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 52.63
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.

-2.77
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

2.3
Log Po/w (WLOGP)?

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

-1.88
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.

1.48
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

0.89
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.0

Water Solubility

Log S (ESOL):?

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

-2.79
Solubility 0.359 mg/ml ; 0.00164 mol/l
Class?

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

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.12
Solubility 1.65 mg/ml ; 0.00753 mol/l
Class?

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

Soluble
Log S (SILICOS-IT)?

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

-1.55
Solubility 6.2 mg/ml ; 0.0283 mol/l
Class?

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

Soluble

Pharmacokinetics

GI absorption?

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

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.

-6.0 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

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)

1.6

Application In Synthesis of [ 85100-77-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 85100-77-2 ]

[ 85100-77-2 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 1493-13-6 ]
  • [ 85100-77-2 ]
  • [ 174899-66-2 ]
YieldReaction ConditionsOperation in experiment
In acetone; at 20℃; for 24h; General procedure: To a solution of the crude 1-butyl-3-methylimidazoliumbromide, obtained from the above reactions,in acetone (70 mL) was added hexafluorophosphoric acid (10.90 g,100.0 mmol). The reaction mixture was stirred for 24 h at room temperature. The resulting mixture was filtered. Evaporation of the solvent under reduced pressure afforded the corresponding 1-Butyl-3-methylimidazolium hexafluorophosphate. Same procedure was used except that trifluoro methane sulphonic acid (15.08 g,100.0 mmol) was used instead of hexafluorophosphoric acid. The resulting mixture was filtered. Evaporation of the solvent under reduced pressure afforded the corresponding imidazolium trifluromethanesulphonate.1-Butyl-3-methylimidazolium tetrafluoroborate was also prepared using the same procedure as above except that tetrafluoro boric acid (15.08 g, 100.0 mmol) was used in place of hexafluorophosphoric acid. Progress of the reaction was measured by TLC. Completion of the reaction was confirmed by 1HNMR.
  • 3
  • [ 2926-27-4 ]
  • [ 85100-77-2 ]
  • [ 174899-66-2 ]
  • 5
  • [ 33454-82-9 ]
  • [ 85100-77-2 ]
  • [ 174899-66-2 ]
YieldReaction ConditionsOperation in experiment
1.382 g In neat (no solvent); at 100℃; for 0.333333h;Microwave irradiation; General procedure: a mixture of 1-methylimidazole (0.4105 g, 5 mmol), 1-bromobutane (0.6850 g, 5 mmol) was heated under microwave irradiation (or conventional heating) in a 10 mL pressurized glass tube fitted with a Teflon-coated septum at 80 C for 20 min. Then, LiOTf (0.78 g, 5 mmol) was added and the mixture was irradiated at 100 C for 20 min. After cooling, the mixture was diluted with MeCN (5 mL), and after removal of the precipitated salt LiBr, the filtrate was then filtered through Celite. The crude product was washed with Et2O and concentrated to give a colorless to pale yellow liquid (1.382 g, 96 % yield). The [BMIM]OTf was dried under reduced pressure. The purity and authenticity of the ionic liquids were confirmed by 1H and 13C NMR spectroscopy.
In acetone; acetonitrile; at 60℃; for 24h; 1-Butyl-3-methylimidazolium bromide was dissolved in acetone/acetonitrile (50:50) and an equimolar amount of LiTfO in acetone was added. The mixture was stirred for 1 day at 60 C and then filtered. The solvent was removed under reduced pressure and the crude product dissolved in CH2Cl2. Upon cooling to 5 C most of the Li halide precipitated and the precipitate was filtered off. The remaining solution was washed halide-free with deionized water (AgNO3 test) and filtered over a column filled with neutral Al2O3 and activated charcoal. The residual organic phase was freed from solvent under reduced pressure and dried under dynamic vacuum for 1-2 days at 80-90 C.
  • 6
  • [ 14172-90-8 ]
  • [ 85100-77-2 ]
  • C0.861N0.04O0.083Co0013Br0005 [ No CAS ]
  • 7
  • [ 85100-77-2 ]
  • [ 174899-66-2 ]
 

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