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Chemical Structure| 619-41-0 Chemical Structure| 619-41-0

Structure of 619-41-0

Chemical Structure| 619-41-0

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Product Details of [ 619-41-0 ]

CAS No. :619-41-0
Formula : C9H9BrO
M.W : 213.07
SMILES Code : C1=C(C=CC(=C1)C)C(CBr)=O
MDL No. :MFCD00000203
InChI Key :KRVGXFREOJHJAX-UHFFFAOYSA-N
Pubchem ID :69272

Safety of [ 619-41-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301+H311+H331-H315-H318
Precautionary Statements:P261-P264-P280-P301+P310+P330-P305+P351+P338+P310-P403+P233
Class:8(6.1)
UN#:2923
Packing Group:

Computational Chemistry of [ 619-41-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.22
Num. rotatable bonds 2
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 49.47
TPSA ?

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

17.07 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.01
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

2.55
Log Po/w (WLOGP)?

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

2.57
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.

2.55
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

3.17
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.57

Water Solubility

Log S (ESOL):?

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

-3.04
Solubility 0.195 mg/ml ; 0.000914 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.

-2.56
Solubility 0.593 mg/ml ; 0.00278 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

-4.0
Solubility 0.0215 mg/ml ; 0.000101 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

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

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.

-5.79 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)

1.5

Application In Synthesis of [ 619-41-0 ]

* 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 [ 619-41-0 ]

[ 619-41-0 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 5319-77-7 ]
  • [ 619-41-0 ]
  • 2-(2-imino-5-methylsulfanyl-[1,3,4]thiadiazol-3-yl)-1-<i>p</i>-tolyl-ethanone [ No CAS ]
  • 2
  • [ 10167-97-2 ]
  • [ 619-41-0 ]
  • [ 142073-96-9 ]
  • 3
  • [ 619-41-0 ]
  • [ 90008-50-7 ]
  • [ 184015-01-8 ]
  • 4
  • [ 51304-61-1 ]
  • [ 619-41-0 ]
  • 2-[4-(4-Chloro-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-1-p-tolyl-ethanone [ No CAS ]
  • 5
  • [ 14292-44-5 ]
  • [ 619-41-0 ]
  • 1-(4-methylphenyl)-2-(5,6,7,8-tetrahydro-2-imino-4H-cycloheptathiazolyl)ethanone hydrobromide [ No CAS ]
  • 6
  • [ 619-41-0 ]
  • [ 4079-54-3 ]
YieldReaction ConditionsOperation in experiment
53% With anhydrous sodium formate; In methanol; for 12h;Reflux; A mixture of 10d (3.0 mmol) and sodium formate (8.0equiv.) in 9 mL MeOH was heated to reflux for 12 h. After the reaction was completed, the mixturewas cool to room temperature, and ethanol was removed in vacuum, diluted with water (10 mL),aqueous layer was extracted with ethyl acetate (3 × 20 mL), and the combined organic phases weredried over Na2SO4, filtered and concentrated. After evaporation, the crude residue was purified bysilica gel column chromatography (200-300 mesh) using petroleum ether and ethyl acetate (15:1, v/v)as eluent to give target compound 15d: Light yellow solid, yield 53%.
  • 7
  • [ 36193-65-4 ]
  • [ 619-41-0 ]
  • [ 1178572-07-0 ]
  • 8
  • [ 60827-45-4 ]
  • [ 619-41-0 ]
  • [ 1207291-14-2 ]
  • [ 1207291-13-1 ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid; In toluene; at 130℃;Product distribution / selectivity; Example 23; Synthesis of (4S)-trans-,cis-2-(4-chlorophenyl)-2-bromomethyl-4-chloromethyl-1,3-dioxolane suppressing halogen exchange between substrates A mixture of 2-bromo-4'-chloroacetophenone (4.94 g, 2-chloro-4'-chloroacetophenone content=0.09%), p-toluenesulfonic acid monohydrate (0.20 g, 0.05 equivalent) and toluene (100 mL) was refluxed at 130C using an azeotropic distillation device with a Dean-Stark tube, and (S)-monochlorohydrin (2.59 g, 1.1 equivalents, >99%ee) was added dropwise under reflux such that the amount of the (S)-monochlorohydrin present in the reaction solution would be not more than 0.1 equivalent (not more than 2.1 mmol) relative to the amount of 2-bromo-4'-chloroacetophenone to be used (21.2 mmol), while analyzing the progress of the reaction by GC. After confirmation of the completion of the azeotropic distillation, the reaction mixture was cooled and washed with 10% aqueous sodium hydrogen carbonate solution and 10% brine. The solvent was evaporated under reduced pressure to give (4S)-trans-,cis-2-(4-chlorophenyl)-2-bromomethyl-4-chloromethyl-1,3-dioxolane (6.56 g, >99%ee). Here, the content percentage of (4S)-trans-,cis-2-(4-chlorophenyl)-2-chloromethyl-4-chloromethyl-1,3-dioxolane halogen-exchanged with a chlorine atom was 0.09%. Examples 30 to 41 Synthesis of (4S)-trans-cis-2-aryl-2-bromomethyl-4-chloromethyl-1,3-dioxolane suppressing halogen exchange In Examples 30 to 41, reactions were performed according to Example 23 and using aryl(bromomethyl)ketones (halogen-exchanged compound content<0.1%) shown in Table 7 and Table 8. The results are shown in Table 9 and Table 10 together with Example 23.
  • 9
  • [ 619-41-0 ]
  • [ 2293-07-4 ]
  • [ 406469-94-1 ]
  • 10
  • [ 3528-17-4 ]
  • [ 100-52-7 ]
  • [ 17356-08-0 ]
  • [ 619-41-0 ]
  • 7-phenyl-9-(p-tolyl)-6,7-dihydrothiazolo[3,2-a]thiochromeno[4,3-d]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% General procedure: A mixture of thiochroman-4-one 1 (1 mmol), benzaldehyde 2(1 mmol), thiourea 3 (1 mmol) was stirred in presence of ionic liquid,[Bmim]HSO4 (1 mL) at 80 C for 20 min followed by the additionof 3-bromo-1-phenylpropan-1-one 4 (1 mmol) and theresulting mixture was further stirred at 80 C for 40-70 min. Theprogress of reaction was monitored by TLC. After completion ofthe reaction, the mixture was diluted with 20 mL of water,2 20 mL of EtOAc was added and shaken vigorously. The organiclayer was separated from the solution. The aqueous layer wasevaporated, the ionic liquid was dried at 60-70 C under vacuumand then reused. The results have shown that the [Bmim]HSO4ionic liquid could be reused at least for four times. The productwas purified by column chromatography on neutral alumina(100-200 mesh), eluted with a solvent system of ethyl acetate-hexane to afford the title compounds 5a-n.
  • 11
  • [ 30748-47-1 ]
  • [ 619-41-0 ]
  • 1-(3-methyl-6-(p-tolyl)imidazo[2,1-b]thiazol-2-yl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With polyethylene glycol (PEG-400); In water; for 0.116667h;Microwave irradiation; Green chemistry; To stirred solution of polyethylene glycol (PEG-400) (2 mL) in water (2 mL) were added 1-(2-amino-4-methylthiazol-5-yl)ethanone (2 mmol)/ethyl 2-amino-4-methylthiazole-5-carboxylate (2 mmol) and α-bromo aralkyl ketones (phenacyl bromides) (2 mmol), and the mixture was heated at 90 C or subject to microwave irradiation at 300 W, until reaction completion as indicated by TLC. After reaction completion, the reaction mixture was cooled at room temperature, and the solid product formed was collected by filtration, washed with water, and recrystallized from ethanol to give pure product. The recovered PEG with water was reused for five further cycles.
  • 12
  • [ 7210-76-6 ]
  • [ 619-41-0 ]
  • [ 940616-19-3 ]
YieldReaction ConditionsOperation in experiment
88% With polyethylene glycol (PEG-400); In water; for 0.133333h;Microwave irradiation; Green chemistry; To stirred solution of polyethylene glycol (PEG-400) (2 mL) in water (2 mL) were added 1-(2-amino-4-methylthiazol-5-yl)ethanone (2 mmol)/ethyl 2-amino-4-methylthiazole-5-carboxylate (2 mmol) and α-bromo aralkyl ketones (phenacyl bromides) (2 mmol), and the mixture was heated at 90 C or subject to microwave irradiation at 300 W, until reaction completion as indicated by TLC. After reaction completion, the reaction mixture was cooled at room temperature, and the solid product formed was collected by filtration, washed with water, and recrystallized from ethanol to give pure product. The recovered PEG with water was reused for five further cycles.
  • 13
  • [ 3382-18-1 ]
  • [ 619-41-0 ]
  • C40H42N2O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With potassium phosphate; In acetonitrile; at 70℃;Molecular sieve; General procedure: A mixture of 3,4-dihydro-isoquinoline imine 1 (0.2 mmol), arylacyl bromides 2 (0.24 mmol), K3PO4 (0.24 mmol), 4Å molecular sieves (powder, 50 mg) and MeCN (0.5 mL) was stirred at 70C for 1.5-3h. Upon the consumption of imine 1 (monitored by TLC), the reaction was cooled to room temperature, filtered, concentrated and purified by a silica gel flash chromatography (PE/EtOAc) to afford compound 3.
  • 14
  • [ 30748-47-1 ]
  • [ 79-19-6 ]
  • [ 619-41-0 ]
  • (E)-4-methyl-5-(1-(2-(4-(p-tolyl)thiazol-2-yl)hydrazono)ethyl)thiazol-2-amine [ No CAS ]
  • 15
  • [ 214834-18-1 ]
  • [ 619-41-0 ]
  • [ 927020-24-4 ]
YieldReaction ConditionsOperation in experiment
96% In ethanol; at 90℃; for 2h; A mixture of 150 mg 2-bromo-1-(4-methylphenyl)ethan-1-one (704 pmol) and 172 mg tert-butyl4-carbamothioylpiperidine-1 -carboxylate (704 pmol) in 2 ml. of ethanol was stirred for 2 h at 90C. The reaction mixture was cooled to room tempe rature and the solvent was evaporated. The crude product was purified by RP-HPLC and obtained in 96% yield (210 mg).1H NMR (400 MHz, DMSO-d6) d ppm 1.80 - 1.95 (m, 2 H) 2.20 (br dd, 2 H) 2.33 (s, 3 H) 2.99 (td, 2 H) 3.27 - 3.41 (m, 4 H) 7.25 (d, 2 H) 7.83 (d, 2 H) 7.95 (s, 1 H).
  • 16
  • [ 7210-76-6 ]
  • [ 619-41-0 ]
  • ethyl 5-(4-methylphenyl)-3-methyl-imidazo[2,1-b]thiazole-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
77.6% In acetone; at 60℃; General procedure: To a solution of 2-amino-4-methylthiazole-5-carboxylate (9, 1.00g, 5.37mmol) in acetone (20ml), the respective 2-bromo-1-(4-substituted-phenyl)ethanone (10-12, 5.37mmol) was added. The solution was refluxed for 24h. Reaction mixture was concentrated under reduced pressure and then purified with column chromatography using hexane:ethylacetate (60:40) to get 13, 14 and 15
  • 17
  • [ 6396-76-5 ]
  • [ 619-41-0 ]
  • N-(2,6-dimethylphenyl)-4-(p-tolyl)thiazol-2-amine [ No CAS ]
 

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Technical Information

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