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[ CAS No. 1114809-11-8 ] {[proInfo.proName]}

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Chemical Structure| 1114809-11-8
Chemical Structure| 1114809-11-8
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Product Details of [ 1114809-11-8 ]

CAS No. :1114809-11-8 MDL No. :MFCD11110260
Formula : C7H3BrClFO Boiling Point : -
Linear Structure Formula :- InChI Key :ADFWZYGIWHXERD-UHFFFAOYSA-N
M.W : 237.45 Pubchem ID :53420270
Synonyms :

Calculated chemistry of [ 1114809-11-8 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.5
TPSA : 17.07 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) : -5.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.71
Log Po/w (XLOGP3) : 2.8
Log Po/w (WLOGP) : 3.47
Log Po/w (MLOGP) : 3.2
Log Po/w (SILICOS-IT) : 3.72
Consensus Log Po/w : 2.98

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.41
Solubility : 0.0916 mg/ml ; 0.000386 mol/l
Class : Soluble
Log S (Ali) : -2.82
Solubility : 0.363 mg/ml ; 0.00153 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.1
Solubility : 0.0189 mg/ml ; 0.0000794 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.73

Safety of [ 1114809-11-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1114809-11-8 ]

* 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 [ 1114809-11-8 ]

[ 1114809-11-8 ] Synthesis Path-Downstream   1~20

  • 1
  • [ 1114809-11-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 2 h / 140 °C 2: tetrabutyl-ammonium chloride; chloro-trimethyl-silane; tert.-butylnitrite / N,N-dimethyl-formamide; dichloromethane / 1 h / 0 - 50 °C 3: ethanol / 1 h / 80 °C / Sealed tube 4: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium acetate / 1,4-dioxane / 2.5 h / 110 °C 5: bis(di-tert-​butyl(4-​dimethylaminophenyl)​phosphine)​dichloropalladium(II); sodium carbonate monohydrate / N,N-dimethyl-formamide; water / 0.5 h / 110 °C
  • 2
  • [ 1114809-11-8 ]
  • [ 1644663-98-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 2 h / 140 °C 2: tetrabutyl-ammonium chloride; chloro-trimethyl-silane; tert.-butylnitrite / N,N-dimethyl-formamide; dichloromethane / 1 h / 0 - 50 °C
  • 3
  • [ 1114809-11-8 ]
  • [ 1644664-00-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 2 h / 140 °C 2: tetrabutyl-ammonium chloride; chloro-trimethyl-silane; tert.-butylnitrite / N,N-dimethyl-formamide; dichloromethane / 1 h / 0 - 50 °C 3: ethanol / 1 h / 80 °C / Sealed tube
  • 4
  • [ 1114809-11-8 ]
  • [ 1644664-02-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 2 h / 140 °C 2: tetrabutyl-ammonium chloride; chloro-trimethyl-silane; tert.-butylnitrite / N,N-dimethyl-formamide; dichloromethane / 1 h / 0 - 50 °C 3: ethanol / 1 h / 80 °C / Sealed tube 4: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium acetate / 1,4-dioxane / 2.5 h / 110 °C
  • 5
  • [ 1114809-11-8 ]
  • [ 1644664-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 2 h / 140 °C 2: tetrabutyl-ammonium chloride; chloro-trimethyl-silane; tert.-butylnitrite / N,N-dimethyl-formamide; dichloromethane / 1 h / 0 - 50 °C 3: ethanol / 1 h / 80 °C / Sealed tube 4: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium acetate / 1,4-dioxane / 2.5 h / 110 °C 5: bis(di-tert-​butyl(4-​dimethylaminophenyl)​phosphine)​dichloropalladium(II); sodium carbonate monohydrate / N,N-dimethyl-formamide; water / 0.5 h / 110 °C 6: iron; acetic acid / ethanol / 2.5 h / 80 °C
  • 7
  • [ 1114809-11-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 16 h / 23 °C 2: N,N-dimethyl-formamide / 3 h / 155 °C 3: sodium tetrahydroborate / methanol / 4 h
  • 8
  • [ 1114809-11-8 ]
  • [ 1802377-15-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 16 h / 23 °C 2: N,N-dimethyl-formamide / 3 h / 155 °C
  • 10
  • [ 1114809-11-8 ]
  • [ 2387488-66-4 ]
YieldReaction ConditionsOperation in experiment
With hydroxylamine hydrochloride; sodium acetate In ethanol at 90℃; 10.a A suspension of the 3-bromo-2-chloro-6-fluorobenzaldehyde (25 g, 105.3 mmol), NH2OH x HCl (8.8 g, 126.4 mmol, 1.2 equiv.) and NaOAc (10.4 g, 126.4 mmol, 1.2 equiv.) in anhydrous EtOH (100 mL) was stirred under reflux for overnight. Reaction was cooled to room temperature, evaporated and the residue was diluted with H2O (300 mL). White solid was filtered off, washed with H2O and dried under vacuum (24.3 g, 91%). Crude product was used in the next step without further purification. ESI MS [M+H]+ for C7H4BrClFNO, calcd 251.9, found 251.9.
With hydroxylamine hydrochloride; sodium acetate In ethanol at 90℃; 10.a A suspension of the 3-bromo-2-chloro-6-fluorobenzaldehyde (25 g, 105.3 mmol), NH2OH x HCl (8.8 g, 126.4 mmol, 1.2 equiv.) and NaOAc (10.4 g, 126.4 mmol, 1.2 equiv.) in anhydrous EtOH (100 mL) was stirred under reflux for overnight. Reaction was cooled to room temperature, evaporated and the residue was diluted with H2O (300 mL). White solid was filtered off, washed with H2O and dried under vacuum (24.3 g, 91%). Crude product was used in the next step without further purification. ESI MS [M+H]+ for C7H4BrClFNO, calcd 251.9, found 251.9.
  • 11
  • [ 1114809-11-8 ]
  • [ 1421620-33-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium acetate; hydroxylamine hydrochloride / ethanol / 90 °C 2: acetic anhydride / 120 °C
  • 12
  • [ 1114809-11-8 ]
  • [ 2385862-58-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium acetate; hydroxylamine hydrochloride / ethanol / 90 °C 2: acetic anhydride / 120 °C 3: N,N-dimethyl-formamide / 2 h / 0 °C
  • 13
  • [ 1114809-11-8 ]
  • [ 2709069-83-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium acetate; hydroxylamine hydrochloride / ethanol / 90 °C 2: acetic anhydride / 120 °C 3: N,N-dimethyl-formamide / 2 h / 0 °C 4: triethylamine; paraquat dichloride / N,N-dimethyl-formamide / 0 - 20 °C
  • 14
  • [ 1114809-11-8 ]
  • [ 2709069-84-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sodium acetate; hydroxylamine hydrochloride / ethanol / 90 °C 2: acetic anhydride / 120 °C 3: N,N-dimethyl-formamide / 2 h / 0 °C 4: triethylamine; paraquat dichloride / N,N-dimethyl-formamide / 0 - 20 °C 5: sodium periodate; rhodium(III) chloride hydrate / dichloromethane; water; acetonitrile / 1.5 h / 20 °C
  • 15
  • [ 1114809-11-8 ]
  • [ 2709067-30-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium acetate; hydroxylamine hydrochloride / ethanol / 90 °C 2: acetic anhydride / 120 °C 3: N,N-dimethyl-formamide / 2 h / 0 °C 4: triethylamine; paraquat dichloride / N,N-dimethyl-formamide / 0 - 20 °C 5: sodium periodate; rhodium(III) chloride hydrate / dichloromethane; water; acetonitrile / 1.5 h / 20 °C 6: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 5 h / 100 °C
  • 16
  • [ 1114809-11-8 ]
  • [ 2708041-02-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium acetate; hydroxylamine hydrochloride / ethanol / 90 °C 2: acetic anhydride / 120 °C 3: acetonitrile / 0 - 20 °C
  • 17
  • [ 1114809-11-8 ]
  • [ 2709069-86-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium acetate; hydroxylamine hydrochloride / ethanol / 90 °C 2: acetic anhydride / 120 °C 3: acetonitrile / 0 - 20 °C 4: sodium periodate; ruthenium trichloride / water; dichloromethane; acetonitrile / 20 °C
  • 18
  • [ 1114809-11-8 ]
  • [ 2709069-68-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sodium acetate; hydroxylamine hydrochloride / ethanol / 90 °C 2: acetic anhydride / 120 °C 3: acetonitrile / 0 - 20 °C 4: sodium periodate; ruthenium trichloride / water; dichloromethane; acetonitrile / 20 °C 5: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane; water / 1.5 h / 80 °C / Sealed tube; Inert atmosphere
  • 19
  • [ 1114809-11-8 ]
  • [ 2709067-21-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium acetate; hydroxylamine hydrochloride / ethanol / 90 °C 2: acetic anhydride / 120 °C 3: acetonitrile / 0 - 20 °C 4: sodium periodate; ruthenium trichloride / water; dichloromethane; acetonitrile / 20 °C 5: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane; water / 1.5 h / 80 °C / Sealed tube; Inert atmosphere 6: hydrogen; palladium 10% on activated carbon / ethyl acetate; methanol / 16 h / 20 °C / 760.05 Torr
  • 20
  • [ 110407-59-5 ]
  • [ 68-12-2 ]
  • [ 1114809-11-8 ]
YieldReaction ConditionsOperation in experiment
70.6% Stage #1: 1-bromo-2-chloro-4-fluorobenzene With lithium dipropan-2-ylazanide In tetrahydrofuran at -78℃; for 0.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78℃; for 0.5h; 54.1 Step 1. 3-bromo-2-chloro-6-fluorobenzaldehyde (392-a) A solution of LDA/THF (2M, 11.9 mL, 23.9 mmol) was added to a mixture of l-bromo-2-chloro- 4-fluoro-benzene (5 g, 23.9 mmol) in THF (100 mL) at -78 °C. The mixture was stirred at -78 °C for 30 minutes. Then DMF (1.84 mL, 23.9 mmol) was added and the mixture was stirred at -78 °C for another 30 minutes. The reaction mixture was diluted with H2O (100 mL) and the mixture was extracted with EtOAc (100 mL x 3). The combined organic phase was washed with brine (100 mL x 2), dried with anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by column chromatography (petroleum ether/EtOAc = 100/0, 254 nm) to afford title compound 392-a as a yellow solid (4 g, 70.6%).
70.6% Stage #1: 1-bromo-2-chloro-4-fluorobenzene With lithium dipropan-2-ylazanide In tetrahydrofuran at -78℃; for 0.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78℃; for 0.5h; 54.1 Step 1. 3-bromo-2-chloro-6-fluorobenzaldehyde (392-a) A solution of LDA/THF (2M, 11.9 mL, 23.9 mmol) was added to a mixture of l-bromo-2-chloro- 4-fluoro-benzene (5 g, 23.9 mmol) in THF (100 mL) at -78 °C. The mixture was stirred at -78 °C for 30 minutes. Then DMF (1.84 mL, 23.9 mmol) was added and the mixture was stirred at -78 °C for another 30 minutes. The reaction mixture was diluted with H2O (100 mL) and the mixture was extracted with EtOAc (100 mL x 3). The combined organic phase was washed with brine (100 mL x 2), dried with anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by column chromatography (petroleum ether/EtOAc = 100/0, 254 nm) to afford title compound 392-a as a yellow solid (4 g, 70.6%).
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