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[ CAS No. 865186-62-5 ] {[proInfo.proName]}

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Product Details of [ 865186-62-5 ]

CAS No. :865186-62-5 MDL No. :MFCD22371190
Formula : C8H6BrFO2 Boiling Point : -
Linear Structure Formula :- InChI Key :OQDUONHFGRRMGY-UHFFFAOYSA-N
M.W : 233.03 Pubchem ID :23157907
Synonyms :

Calculated chemistry of [ 865186-62-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.98
TPSA : 26.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.2 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.02
Log Po/w (XLOGP3) : 2.15
Log Po/w (WLOGP) : 2.83
Log Po/w (MLOGP) : 2.28
Log Po/w (SILICOS-IT) : 3.08
Consensus Log Po/w : 2.47

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.88
Solubility : 0.309 mg/ml ; 0.00133 mol/l
Class : Soluble
Log S (Ali) : -2.33
Solubility : 1.08 mg/ml ; 0.00463 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.61
Solubility : 0.0569 mg/ml ; 0.000244 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.52

Safety of [ 865186-62-5 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 865186-62-5 ]

* 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 [ 865186-62-5 ]

[ 865186-62-5 ] Synthesis Path-Downstream   1~25

  • 1
  • [ 861928-19-0 ]
  • [ 33513-42-7 ]
  • 2-bromo-5-fluoro-4-methoxybenzaldehyde [ No CAS ]
  • [ 865186-62-5 ]
  • 2,3-dibromo-5-fluoro-6-methoxybenzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
13% Stage #1: 4,5-dibromo-2-fluoroanisole With n-butyllithium In tetrahydrofuran; diethyl ether at -100℃; for 0.25h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; diethyl ether at -100℃; for 0.25h;
  • 2
  • 4,5-dibromo-2-fluorophenol [ No CAS ]
  • [ 865186-62-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 91 percent / NaOH / H2O 2.1: BuLi / diethyl ether; tetrahydrofuran / 0.25 h / -100 °C 2.2: diethyl ether; tetrahydrofuran / 0.25 h / -100 °C
  • 3
  • [ 112204-58-7 ]
  • [ 865186-62-5 ]
  • 4
  • [ 112204-57-6 ]
  • [ 865186-62-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 22 g / NaOH; H2O2 / H2O / 30 - 35 °C 2.1: 14 g / Br2 / CHCl3 / 20 °C 3.1: 91 percent / NaOH / H2O 4.1: BuLi / diethyl ether; tetrahydrofuran / 0.25 h / -100 °C 4.2: diethyl ether; tetrahydrofuran / 0.25 h / -100 °C
  • 5
  • [ 128495-46-5 ]
  • [ 865186-62-5 ]
YieldReaction ConditionsOperation in experiment
92% With bromine; potassium bromide; In water; at 20℃; Intermediate .: 6-Fluorobenzofc] ' [l,2]oxaborole-l,5(3H)-diol[0504] A solution of <strong>[128495-46-5]4-fluoro-3-methoxybenzaldehyde</strong> (4.3 g, 28 mmol), potassium bromide (16.6 g, 140 mmol), bromine (3.6 mL, 70 mmol), and water (45 mL) were stirred at room temperature for 24 hours. More bromine (1.4 mL, 28 mmol) was added and the reaction was stirred at room temperature overnight. The product precipitated out of solution and was collected via filtration and dried under reduced pressure to give 2-bromo-4-fluoro-5-methoxybenzaldehyde (6.01 g, 92%).
92% With bromine; potassium bromide; In water; at 20℃; A solution of <strong>[128495-46-5]4-fluoro-3-methoxybenzaldehyde</strong> (4.3 g, 27.9 mmol), potassium bromide (16.6 g, 139.5 mmol), bromine (3.6 mL, 69.8 mmol), and water (45 mL) were stirred at room temperature for 24 hours. More bromine (1.43 mL, 27.9 mmol) was added and the reaction was stirred at room temperature overnight. The product precipitated out of solution and was collected via filtration and dried under reduced pressure to give 2-bromo-4-fluoro-5-methoxybenzaldehyde (6.01 g, 92% yield).
91% With bromine; potassium bromide; In water; at 20℃; for 6h; Reference Example 40 2-Bromo-4-fluoro-5-methoxybenzaldehyde (Compound ar) To a mixture of water (90 mL), potassium bromide (33.9 g, 285 mmol) and bromine (7.33 mL, 142 mmol) was added <strong>[128495-46-5]4-fluoro-3-methoxybenzaldehyde</strong> (8.77 g, 56.9 mmol), and the mixture was stirred at room temperature for 6 hours. The resulting crystal was collected by filtration to give Compound ar (11.9 g, 91 %).
  • 6
  • [ 865186-62-5 ]
  • [ 149-73-5 ]
  • [ 865186-63-6 ]
YieldReaction ConditionsOperation in experiment
100% In methanol for 1.5h; Heating / reflux; 41 2-Bromo-4-fluoro-5-methoxybenzaldehyde dimethyl acetal (Compound as) Reference Example 41 2-Bromo-4-fluoro-5-methoxybenzaldehyde dimethyl acetal (Compound as) Compound ar (6.00 g, 25.8 mmol) was dissolved in methanol (150 mL), and trimethyl orthoformate (8.45 mL, 77.3 mmol) and p-toluenesulfonic acid (490 mg, 2.58 mmol) were added thereto, and then the mixture was heated under reflux for 1.5 hours. To the reaction mixture were added saturated aqueous sodium hydrogencarbonate and chloroform, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give Compound as (7.19 g, 100 %). 1H NMR (DMSO-d6, δ): 3.30 (s, 6H), 3.85 (s, 3H), 5.41 (s, 1H), 7.22 (d, J = 9.2 Hz, 1H), 7.59 (d, J = 10.7 Hz, 1H).
  • 7
  • [ 865186-62-5 ]
  • [ 1262989-52-5 ]
YieldReaction ConditionsOperation in experiment
94% With hydrogen bromide; acetic acid at 130℃; for 24h; 22.2 Step 2: 2-bromo-4-fluoro-5-hydroxybenzaldehyde (2): A solution of 1 (5.0 g, 21 mmol) in HBr (50 mL) and AcOH (50 mL) was stirred at 130 °C for 24 hours. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was quenched by addition sat. aqueous NaHCCb to pH = 7 and water (100 mL), then diluted with ethyl acetate (300 mL), and extracted with ethyl acetate (200 mL x 3). The combined organic layers were washed with sat. brine (100 mL), dried over NaiSCL, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (S1O2, petroleum ether/ethyl acetate, 20:1 to 1 : 1) to give 2 (4.5 g, 94% yield) as a yellow solid. LCMS: tR = 0.375 min, (ES-) m/z (M-H) = 216.9.
64% With hydrogen bromide In acetic acid at 130℃; for 5h; 2 [0505] A solution of 2-bromo-4-fluoro-5-methoxybenzaldehyde (1.19 g, 8.20 mmol), 48% HBr (57 mL) and glacier acetic acid (57 mL) were refluxed at 130 °C for 5 h. The glacier acetic acid was removed under reduced pressure. The solution was neutralized using sodium carbonate. Water was added and the mixture was extracted using ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and filtered. The solvent was removed under reduced pressure. The residue was purified by silica gel column using Combiflash to give 2-bromo-4-fluoro- 5-hydroxybenzaldehyde (1.15 g, 64%).
64% With hydrogen bromide; acetic acid at 130℃; for 5h; Reflux; 19.19dy A solution of 2-bromo-4-fluoro-5-methoxybenzaldehyde (1.19 g, 8.20 mmol), 48% HBr (57 mL) and glacier acetic acid (57 mL) were refluxed at 130° C. for 5 hours. The glacier acetic acid was removed under reduced pressure. The solution was neutralized using sodium carbonate. Water was added and the mixture was extracted using ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and filtered. The solvent was removed under reduced pressure. The residue was purified by silica gel column using Combiflash to give 2-bromo-4-fluoro-5-hydroxybenzaldehyde (1.15 g, 64% yield).
  • 8
  • [ 865186-62-5 ]
  • [ 1319804-06-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogen bromide / acetic acid / 5 h / 130 °C 2: methanol; sodium tetrahydroborate / 1 h / 20 °C / Cooling with ice
  • 9
  • [ 865186-62-5 ]
  • [ 1319804-07-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogen bromide / acetic acid / 5 h / 130 °C 2: methanol; sodium tetrahydroborate / 1 h / 20 °C / Cooling with ice 3: camphor-10-sulfonic acid / dichloromethane / 21 h / 20 °C
  • 10
  • [ 865186-62-5 ]
  • [ 1319803-98-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: hydrogen bromide / acetic acid / 5 h / 130 °C 2.1: methanol; sodium tetrahydroborate / 1 h / 20 °C / Cooling with ice 3.1: camphor-10-sulfonic acid / dichloromethane / 21 h / 20 °C 4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C 4.2: 2 h / 20 °C
  • 11
  • [ 865186-62-5 ]
  • [ 89-25-8 ]
  • 7-fluoro-6-methoxy-3-methyl-1-phenylchromeno[2,3-c]pyrazol-4(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In dimethyl sulfoxide at 120℃; for 6h; Sealed tube;
  • 12
  • [ 865186-62-5 ]
  • (S)-tryptophan methyl ester hydrochloride [ No CAS ]
  • C20H18BrFN2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-bromo-4-fluoro-5-methoxylbenzaldehyde; (S)-tryptophan methyl ester hydrochloride In dichloromethane for 24h; Molecular sieve; Stage #2: With trifluoroacetic acid In dichloromethane Molecular sieve;
  • 13
  • [ 865186-62-5 ]
  • [ 536-74-3 ]
  • C16H11FO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine In tetrahydrofuran at 70 - 80℃; for 12h; Inert atmosphere; Schlenk technique;
  • 14
  • [ 865186-62-5 ]
  • 3-fluoro-2-methoxy-6-phenylbenzo[4,5]imidazo[2,1-a]isoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trans-bis(triphenylphosphine)palladium dichloride; copper(l) iodide; triethylamine / tetrahydrofuran / 12 h / 70 - 80 °C / Inert atmosphere; Schlenk technique 2: ethanol / 6 h / 50 °C / Green chemistry
  • 15
  • [ 865186-62-5 ]
  • 3-fluoro-2-methoxy-9,10-dimethyl-6-phenylbenzo[4,5]imidazo[2,1-a]isoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trans-bis(triphenylphosphine)palladium dichloride; copper(l) iodide; triethylamine / tetrahydrofuran / 12 h / 70 - 80 °C / Inert atmosphere; Schlenk technique 2: ethanol / 6 h / 50 °C / Green chemistry
  • 16
  • [ 865186-62-5 ]
  • [ 1066-54-2 ]
  • 4-fluoro-5-methoxy-2-((trimethylsilyl)ethynyl)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 50℃; Inert atmosphere;
  • 17
  • [ 865186-62-5 ]
  • 4-fluoro-5-methoxy-2-((4-(trifluoromethyl)phenyl)ethynyl)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 50 °C / Inert atmosphere 2: potassium carbonate; methanol / 0.25 h / 20 °C 3: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere
  • 18
  • [ 865186-62-5 ]
  • C10H7FO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 50 °C / Inert atmosphere 2: potassium carbonate; methanol / 0.25 h / 20 °C
YieldReaction ConditionsOperation in experiment
Embodiment 4036:(S)-N-ethyl-2-(10-fluoro-7-(4-flurophenyl)-9-methoxyl-2-methyl-3-oxo-3,5-dihydro-2H-benzo [c]pyrido[3,4-e]azepin-5-yl)acetamideStep 1: 2-bromo-4-fluoro-5-methoxylbenzaldehydeStep 2: (2-bromo-4fluoro-5-methoxylbenzyl)(4-flurophenyl)methanol
  • 20
  • [ 865186-62-5 ]
  • 4-bromo-5-((diisopropylamino)methyl)-2-fluorophenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydrogen bromide; acetic acid / 24 h / 130 °C 2.1: triethylamine / 1,2-dichloro-ethane / 12 h / 25 °C 2.2: 48 h / 25 °C
  • 21
  • [ 865186-62-5 ]
  • 5-((diisopropylamino)methyl)-2-fluoro-4-(2-methoxypyridin-4-yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hydrogen bromide; acetic acid / 24 h / 130 °C 2.1: triethylamine / 1,2-dichloro-ethane / 12 h / 25 °C 2.2: 48 h / 25 °C 3.1: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / water; 1,4-dioxane / 12 h / 70 °C / Inert atmosphere
  • 22
  • [ 865186-62-5 ]
  • 5-((diisopropylamino)methyl)-2-fluoro-4-(2-methoxypyridin-4-yl)phenyl 3-((1R,2S)-3-(tert-butoxy)-1-cyclopropyl-2-methyl-3-oxopropyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: hydrogen bromide; acetic acid / 24 h / 130 °C 2.1: triethylamine / 1,2-dichloro-ethane / 12 h / 25 °C 2.2: 48 h / 25 °C 3.1: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / water; 1,4-dioxane / 12 h / 70 °C / Inert atmosphere 4.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 12 h / 25 °C
  • 23
  • [ 865186-62-5 ]
  • (2S,3R)-3-cyclopropyl-3-(3-((5-((diisopropylamino)methyl)-2-fluoro-4-(2-methoxypyridin-4-yl)phenoxy)carbonyl)phenyl)-2-methylpropanoic acid formic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: hydrogen bromide; acetic acid / 24 h / 130 °C 2.1: triethylamine / 1,2-dichloro-ethane / 12 h / 25 °C 2.2: 48 h / 25 °C 3.1: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / water; 1,4-dioxane / 12 h / 70 °C / Inert atmosphere 4.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 12 h / 25 °C 5.1: trifluoroacetic acid / dichloromethane / 0.5 h / 25 °C
  • 24
  • [ 865186-62-5 ]
  • 6-fluoro-5-methoxy-1H-indazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanol / 3 h / Reflux 2: caesium carbonate; copper(l) iodide; N,N`-dimethylethylenediamine / N,N-dimethyl-formamide / 5 h / 120 °C / Sealed tube
  • 25
  • [ 865186-62-5 ]
  • [ 1937-19-5 ]
  • (E)-2-(2-bromo-4-fluoro-5-methoxybenzylidene)hydrazine-1-carboximidamide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% In ethanol for 3h; Reflux; 4.2.1. General procedure I for the synthesis of starting materials (E)-1aa-o [24] General procedure: A stirred solution of aminoguanidine hydrochloride (4) (5 mmol, 1.0 equiv) and a 2-bromobenzaldehyde 3 (5 mmol, 1.0 equiv) in EtOH (3.0 mL/mmol aldehyde) was heated under reflux (100 °C, oil bath temperature) for 3 h. The reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. The remaining solid was subjected to filtration and the filter cake was washed thoroughly with cyclohexane (3 x 50 mL). The crude product was purified by recrystallization using mixtures of EtOH and H2O to afford the corresponding (E)-2-(2-bromobenzylidene)hydrazine-1-carboximidamide hydrochloride (E)-1 in analytically pure form.
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