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Chemical Structure| 61047-43-6 Chemical Structure| 61047-43-6

Structure of 8-Bromo-2-methylquinoline
CAS No.: 61047-43-6

Chemical Structure| 61047-43-6

8-Bromo-2-methylquinoline

CAS No.: 61047-43-6

4.5 *For Research Use Only !

Cat. No.: A383087 Purity: 97%

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Product Details of [ 61047-43-6 ]

CAS No. :61047-43-6
Formula : C10H8BrN
M.W : 222.08
SMILES Code : CC1=NC2=C(Br)C=CC=C2C=C1
MDL No. :MFCD04966997
InChI Key :GQPRZSFQSOEDNV-UHFFFAOYSA-N
Pubchem ID :4715030

Safety of [ 61047-43-6 ]

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

Computational Chemistry of [ 61047-43-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 10
Fraction Csp3 0.1
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 54.41
TPSA ?

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

12.89 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.33
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

3.38
Log Po/w (WLOGP)?

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

3.31
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.

2.85
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

3.6
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.09

Water Solubility

Log S (ESOL):?

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

-3.96
Solubility 0.0242 mg/ml ; 0.000109 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.

-3.33
Solubility 0.104 mg/ml ; 0.000468 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

-4.95
Solubility 0.00251 mg/ml ; 0.0000113 mol/l
Class?

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

Moderately 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

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.

-5.25 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)

1.32

Application In Synthesis of [ 61047-43-6 ]

* 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 [ 61047-43-6 ]

[ 61047-43-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 61047-43-6 ]
  • [ 904886-25-5 ]
YieldReaction ConditionsOperation in experiment
85% With selenium(IV) oxide; In 1,4-dioxane; at 100℃; In a round bottom flask, add 8-bromo-2-methylquinoline (1.110g, 5mmol), selenium dioxide (1.110g, 10mmol), 30ml dioxane, and heat to 100C. TLC monitor the reaction until All raw materials react. After the reaction was cooled to room temperature, the organic phase was filtered and concentrated to obtain a crude product. The product was purified using column chromatography. Obtained 1.006 g of 8-bromo-2-quinolinecarboxaldehyde with a yield of 85%
3.1 g With selenium(IV) oxide; In 1,4-dioxane; at 60℃; To a suspension of selenium dioxide (2.5 g, 23.0 mmol) in dioxane (15 mL) at 60 C was added a solution of 8-bromo-2-methylquinoline (3 g, 13.5 mmol) in dioxane (15 mL). Resulted mixture turned dark brown after 30 min at 60 C. The heating continued until reagents were consumed. The mixture was cooled down to rt, filtered and concentrated in vacuo. The cream solid was used without additional purification(3.1 g).
With selenium(IV) oxide; In 1,4-dioxane; water;Reflux; General procedure: A solution of the quinaldine (1.0 equiv.) and selenium dioxide (1.7 equiv.) in dioxane/water was heated under reflux monitored by thin-layer chromatography (TLC). The solid formed was filtered and washed with dichloromethane (2 × 2 mL). The filtrates were combined and the solvent removed under reduced pressure and the resulting oily residue was purified by column chromatography in dichloromethane.
With selenium(IV) oxide; In 1,4-dioxane;Inert atmosphere; Reflux; Add 1.1 molar equivalent of crotonaldehyde to the hydrochloric acid solution of 2-bromoaniline, Reflux overnight at 100C, add 1 molar equivalent of zinc chloride to the aqueous phase obtained after adding ether at room temperature, The obtained yellow solid was washed once with isopropanol and hydrochloric acid, Add water and ammonia water in a volume ratio of 3:1, stir, add ether, and remove the organic phase to obtain 8-bromo-2-methylquinoline. Under nitrogen atmosphere, 8-bromo-2-methylquinoline and 1 molar equivalent of selenium dioxide were refluxed overnight in dioxane, the reaction solution was suction filtered at room temperature, and the filtrate was concentrated to obtain 8-Bromo-2quinolinecarboxaldehyde. Under a nitrogen atmosphere, dissolve the substituted aniline in toluene, add 1-1.5 molar equivalents of trimethylaluminum at room temperature, reflux for 4-6 hours, add the toluene solution of 8-bromo-2quinolinecarboxaldehyde, and reflux for 8- 12 hours; A 5% NaOH aqueous solution was added, the organic phase was dried, and after the organic solvent was removed under reduced pressure, a small amount of methanol solvent was added to obtain a yellow solid, that is, the imine intermediate. Under a nitrogen atmosphere, differently substituted imine intermediates and 1 molar equivalent of differently substituted mercaptans were coupled to synthesize ligands under palladium catalysis. Under nitrogen atmosphere, weigh the ligand (0.429g, 1.1mmol), Add 20mL of dry dichloromethane to dissolve, weigh [CrCl3(THF)3] (0.371g, 1mmol), add 20mL of dry dichloromethane, introduce the ligand solution into the latter, stir for 12 hours to obtain a green suspension liquid. Concentrate to 5-10 mL, add 5 mL of dry ether, filter, and then add 5 mL of dry ether to wash once, filter to obtain 0.46 g of green powder Cr1 compound, with a yield of 85%.

 

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