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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 : |
|
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 |
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 |
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 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
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 |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.73 |
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: |
* 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.
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 140℃; for 2h; |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 23℃; for 16h; |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium acetate; hydroxylamine hydrochloride / ethanol / 90 °C 2: acetic anhydride / 120 °C |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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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