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[ CAS No. 104222-42-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 104222-42-6
Chemical Structure| 104222-42-6
Chemical Structure| 104222-42-6
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Product Details of [ 104222-42-6 ]

CAS No. :104222-42-6 MDL No. :MFCD05664065
Formula : C7H2BrF3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :VWVLSESGZBAPHA-UHFFFAOYSA-N
M.W : 254.99 Pubchem ID :2783246
Synonyms :

Calculated chemistry of [ 104222-42-6 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.98
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.47
Log Po/w (XLOGP3) : 2.44
Log Po/w (WLOGP) : 3.83
Log Po/w (MLOGP) : 3.63
Log Po/w (SILICOS-IT) : 3.21
Consensus Log Po/w : 2.91

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.23
Solubility : 0.149 mg/ml ; 0.000584 mol/l
Class : Soluble
Log S (Ali) : -2.87
Solubility : 0.347 mg/ml ; 0.00136 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.47
Solubility : 0.0872 mg/ml ; 0.000342 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.72

Safety of [ 104222-42-6 ]

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 [ 104222-42-6 ]

* 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 [ 104222-42-6 ]

[ 104222-42-6 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 104222-42-6 ]
  • [ 104222-44-8 ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 18h; Ambient temperature;
In thionyl chloride 10 3-Bromo-2,4,5-trifluorobenzoyl chloride EXAMPLE 10. 3-Bromo-2,4,5-trifluorobenzoyl chloride A solution of the 3-bromo-2,4,5-trifluorobenzoic acid (2.5 g) in thionyl chloride (10 ml) was refluxed for 2.5 hours, and then concentrated. The resulting residue was purified by distillation through Widmer fractionating column to give the title compound (2.3 g), bp 98°-102° C./18 mmHg.
  • 2
  • [ 182937-75-3 ]
  • [ 104222-42-6 ]
YieldReaction ConditionsOperation in experiment
45% With hydrogenchloride for 6h; Heating;
  • 3
  • [ 125290-72-4 ]
  • [ 104222-42-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) LDA, 2.) 1,2-dibromotetrafluoroethane / 1.) THF, -78 deg C, 1 h, 2.) THF, from -78 deg C to RT 2: 45 percent / 4.5 M aq. HCl / 6 h / Heating
  • 4
  • [ 104222-42-6 ]
  • [ 104222-46-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (COCl)2, DMF / CH2Cl2 / 18 h / Ambient temperature 2: 1.) isopropylmagnesium chloride / 1.) THF, -78 deg C, 30 min, 2.) THF, from -78 deg C to RT
  • 5
  • [ 104222-42-6 ]
  • [ 104222-48-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (COCl)2, DMF / CH2Cl2 / 18 h / Ambient temperature 2: 1.) isopropylmagnesium chloride / 1.) THF, -78 deg C, 30 min, 2.) THF, from -78 deg C to RT 3: 1.) Ac2O / 1.) 130 deg C, 3 h, 2.) Et2O, RT, 18 h
  • 6
  • [ 104222-42-6 ]
  • [ 104222-50-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: (COCl)2, DMF / CH2Cl2 / 18 h / Ambient temperature 2: 1.) isopropylmagnesium chloride / 1.) THF, -78 deg C, 30 min, 2.) THF, from -78 deg C to RT 3: 1.) Ac2O / 1.) 130 deg C, 3 h, 2.) Et2O, RT, 18 h 4: NaH / tetrahydrofuran / 1.5 h / Ambient temperature 5: 48 percent / 6M aq. HCl / 3 h / Heating
  • 7
  • [ 104222-42-6 ]
  • [ 104222-49-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (COCl)2, DMF / CH2Cl2 / 18 h / Ambient temperature 2: 1.) isopropylmagnesium chloride / 1.) THF, -78 deg C, 30 min, 2.) THF, from -78 deg C to RT 3: 1.) Ac2O / 1.) 130 deg C, 3 h, 2.) Et2O, RT, 18 h 4: NaH / tetrahydrofuran / 1.5 h / Ambient temperature
YieldReaction ConditionsOperation in experiment
R.4 2) Using anhydrous cuprous bromide in otherwise the same manner as above, 3-bromo-2,4,5-trifluorobenzoic acid (compound 29) was synthesised. m.p.: 124°-125° C.
  • 9
  • [ 104222-42-6 ]
  • [ 446-17-3 ]
YieldReaction ConditionsOperation in experiment
With sodium acetate; acetic acid;palladium; 3-2 Reduction of the bromo-compound A mixture consisting of 5.0 g of 3-bromo-2,4,5-trifluorobenzoic acid 29, 30 ml of acetic acid, 2.0 g of sodium acetate and 1.0 g of 5% palladium-on-carbon was subjected to a reduction reaction in a hydrogen atmosphere for 4 hours. The catalyst was then filtered off and the filtrate was concentrated to dryness under reduced pressure. The residue was extracted with ethyl acetate and the extract was washed with water and dried over anhydrous sodium sulfate. Finally, the solvent was removed under reduced pressure to give 3.2 g of title compound 30 as colorless crystals. 1 H-NMR (CDCl3) deltappm:
  • 10
  • 18N-sulfuric acid [ No CAS ]
  • 3-bromo-2,4,5-trifluorobenzamide [ No CAS ]
  • [ 104222-42-6 ]
YieldReaction ConditionsOperation in experiment
9 3-Bromo-2,4,5-trifluorobenzoic acid A mixture of 3-bromo-2,4,5-trifluorobenzamide (8.7 g) and 18N-sulfuric acid (50 ml) was stirred at 100° C. for 4 hours, and then poured into ice water (200 ml). The resulting precipitate was collected by filtration and recrystallized from dichloro-methane-n-hexane to give the title compound (6.9 g), mp 125°-127° C.
  • 11
  • [ 104222-42-6 ]
  • ethyl 2-(2-bromo-5-methyl-3,4,6-trifluorobenzoyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.08 h / -78 °C / Inert atmosphere 1.2: 3 h / 20 °C 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane 2.2: 23 h / 0 - 20 °C
  • 12
  • [ 104222-42-6 ]
  • [ 74-88-4 ]
  • 2-bromo-5-methyl-3,4,6-trifluorobenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.1 g Stage #1: 3-bromo-2,4,5-trifluorobenzoic acid With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1.08333h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; hexane at 20℃; for 3h; 60 Reference Example 60
2-Bromo-5-methyl-3,4,6-trifluorobenzoic acid
24 mL of anhydrous tetrahydrofuran was added to 4.8 mL of diisopropylamine and the mixture was stirred in a nitrogen atmosphere at -78° C. 22 mL of a 1.6 mol/L n-butyllithium solution in n-hexane was added dropwise to the mixture over 45 minutes at -78° C. and the mixture was stirred at the same temperature for 10 minutes. A solution of 3-bromo-2,4,5-trifluorobenzoic acid (4.1 g) in 24 mL of anhydrous tetrahydrofuran was added dropwise to the reaction solution over 20 minutes at -78° C. and the mixture was stirred at the same temperature for 45 minutes. 1.5 mL of iodomethane was added to the reaction solution and the mixture was stirred at room temperature for 3 hours. 100 mL of 1 mol/L hydrochloric acid was added to the reaction solution to adjust pH to approximately 5 and then the mixture was extracted three times with 100 mL of ethyl acetate. The extract was washed with 100 mL of 1 mol/L hydrochloric acid and 100 mL of saturated brine and then dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was filtered off and then the solvent was evaporated under reduced pressure. The resulting crystalline residue was collected by filtration with toluene to obtain 2.1 g of the title compound as a light brown solid. 1H-NMR (DMSO-d6); δ 2.19 (3H, t, J=1.9 Hz).
  • 13
  • [ 104222-42-6 ]
  • ethyl 2-(2-bromo-5-methyl-3,4,6-trifluorobenzoyl)-3-ethoxyacrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.08 h / -78 °C / Inert atmosphere 1.2: 3 h / 20 °C 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane 2.2: 23 h / 0 - 20 °C 3.1: acetic anhydride / 5.5 h / 120 °C
  • 14
  • [ 104222-42-6 ]
  • ethyl 5-bromo-6,7-difluoro-1-[5-(2,4-dimethoxybenzylamino)-4-fluoro-2-(hydroxymethyl)phenyl]-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.08 h / -78 °C / Inert atmosphere 1.2: 3 h / 20 °C 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane 2.2: 23 h / 0 - 20 °C 3.1: acetic anhydride / 5.5 h / 120 °C 4.1: lithium borohydride / tetrahydrofuran; toluene / 6 h / Reflux 4.2: 40 h / 20 °C 4.3: 2 h / 60 °C
  • 15
  • [ 104222-42-6 ]
  • ethyl 1-[5-amino-4-fluoro-2-(hydroxymethyl)phenyl]-5-bromo-6,7-difluoro-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.08 h / -78 °C / Inert atmosphere 1.2: 3 h / 20 °C 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane 2.2: 23 h / 0 - 20 °C 3.1: acetic anhydride / 5.5 h / 120 °C 4.1: lithium borohydride / tetrahydrofuran; toluene / 6 h / Reflux 4.2: 40 h / 20 °C 4.3: 2 h / 60 °C 5.1: trifluoroacetic acid / dichloromethane / 0.33 h / 20 °C
  • 16
  • [ 104222-42-6 ]
  • ethyl 1-[5-amino-4-fluoro-2-(hydroxymethyl)phenyl]-5-bromo-6-fluoro-7-[3-hydroxyazetidin-1-yl]-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.08 h / -78 °C / Inert atmosphere 1.2: 3 h / 20 °C 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane 2.2: 23 h / 0 - 20 °C 3.1: acetic anhydride / 5.5 h / 120 °C 4.1: lithium borohydride / tetrahydrofuran; toluene / 6 h / Reflux 4.2: 40 h / 20 °C 4.3: 2 h / 60 °C 5.1: trifluoroacetic acid / dichloromethane / 0.33 h / 20 °C 6.1: 1-Methylpyrrolidine / dimethyl sulfoxide / 139.5 h / 50 - 70 °C
  • 17
  • [ 104222-42-6 ]
  • 1-[5-amino-4-fluoro-2-(hydroxymethyl)phenyl]-5-bromo-6-fluoro-7-(3-hydroxyazetidin-1-yl)-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.08 h / -78 °C / Inert atmosphere 1.2: 3 h / 20 °C 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane 2.2: 23 h / 0 - 20 °C 3.1: acetic anhydride / 5.5 h / 120 °C 4.1: lithium borohydride / tetrahydrofuran; toluene / 6 h / Reflux 4.2: 40 h / 20 °C 4.3: 2 h / 60 °C 5.1: trifluoroacetic acid / dichloromethane / 0.33 h / 20 °C 6.1: 1-Methylpyrrolidine / dimethyl sulfoxide / 139.5 h / 50 - 70 °C 7.1: sodium hydroxide; water / ethanol / 1.5 h / 50 °C
  • 18
  • [ 104222-42-6 ]
  • 1-[5-amino-4-fluoro-2-(hydroxymethyl)phenyl]-5-bromo-6,7-difluoro-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.08 h / -78 °C / Inert atmosphere 1.2: 3 h / 20 °C 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane 2.2: 23 h / 0 - 20 °C 3.1: acetic anhydride / 5.5 h / 120 °C 4.1: lithium borohydride / tetrahydrofuran; toluene / 6 h / Reflux 4.2: 40 h / 20 °C 4.3: 2 h / 60 °C 5.1: trifluoroacetic acid / dichloromethane / 0.33 h / 20 °C 6.1: sodium hydroxide; water / ethanol / 0.5 h / 50 °C
  • 19
  • [ 104222-42-6 ]
  • 1-[5-amino-4-fluoro-2-(hydroxymethyl)phenyl]-5-bromo-6-fluoro-8-methyl-7-(3-methylaminoazetidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.08 h / -78 °C / Inert atmosphere 1.2: 3 h / 20 °C 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane 2.2: 23 h / 0 - 20 °C 3.1: acetic anhydride / 5.5 h / 120 °C 4.1: lithium borohydride / tetrahydrofuran; toluene / 6 h / Reflux 4.2: 40 h / 20 °C 4.3: 2 h / 60 °C 5.1: trifluoroacetic acid / dichloromethane / 0.33 h / 20 °C 6.1: sodium hydroxide; water / ethanol / 0.5 h / 50 °C 7.1: lithium chloride; N,N,N',N'-tetramethylguanidine / dimethyl sulfoxide / 31 h / 50 °C
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