Conditions | Yield |
---|---|
Stage #1: Benzo[b]thiophene With dihydrogen peroxide; acetic acid at 78℃; for 0.5h; Inert atmosphere; Stage #2: With tetrabutylammomium bromide; sodium bromide In water at 120℃; under 7220.48 Torr; for 20h; | 98.8% |
Conditions | Yield |
---|---|
With acetic acid; silver carbonate In dimethyl sulfoxide at 120℃; Further stages; | 95% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl acetamide at 200℃; for 1h; microwave irradiation; | 91% |
With triethylenediamine at 120 - 180℃; for 6h; | 91.7% |
4,7-dibromobenzo[b]thiophene
4-bromobenzo[b]thiophene
Conditions | Yield |
---|---|
Stage #1: 4,7-dibromobenzo[b]thiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: With methanol In tetrahydrofuran; hexane at -78℃; | 53% |
1-bromo-3-[(2,2-dimethoxyethyl)sulfanyl]benzene
4-bromobenzo[b]thiophene
Conditions | Yield |
---|---|
In chlorobenzene | 14% |
benzo[B]thiophen-4-ylamine
4-bromobenzo[b]thiophene
Conditions | Yield |
---|---|
With hydrogen bromide; sodium nitrite Behandeln der Reaktionsloesung mit Kupfer(I)-bromid; |
Conditions | Yield |
---|---|
With sulfuric acid; sodium nitrite Behandeln des Diazoniumsalzes mit wss. Hypophosphorigsaeure ; |
1-bromo-3-(2,2-diethoxy-ethylsulfanyl)benzene
4-bromobenzo[b]thiophene
Conditions | Yield |
---|---|
Stage #1: 1-bromo-3-(2,2-diethoxy-ethylsulfanyl)benzene With PPA In chlorobenzene at 130℃; for 1h; Stage #2: With sodium hydroxide In water; chlorobenzene at 20℃; |
4-nitrobenzene[b]thiophene
4-bromobenzo[b]thiophene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: palladium/charcoal; ethanol / Hydrogenation 2: aqueous hydrobromic acid; sodium nitrite / Behandeln der Reaktionsloesung mit Kupfer(I)-bromid View Scheme |
benzo[b]thiophen-5-yl-acetamide
4-bromobenzo[b]thiophene
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: nitric acid 2: aq.-ethanolic NaOH-solution 3: aqueous sulfuric acid; sodium nitrite / Behandeln der Reaktionsloesung mit wss. Hypophosphorigsaeure 4: palladium/charcoal; ethanol / Hydrogenation 5: aqueous hydrobromic acid; sodium nitrite / Behandeln der Reaktionsloesung mit Kupfer(I)-bromid View Scheme |
4-nitro-benzo[b]thiophen-5-ylamine
4-bromobenzo[b]thiophene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aqueous sulfuric acid; sodium nitrite / Behandeln der Reaktionsloesung mit wss. Hypophosphorigsaeure 2: palladium/charcoal; ethanol / Hydrogenation 3: aqueous hydrobromic acid; sodium nitrite / Behandeln der Reaktionsloesung mit Kupfer(I)-bromid View Scheme |
N-(4-nitro-benzo[b]thiophen-5-yl)-acetamide
4-bromobenzo[b]thiophene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: aq.-ethanolic NaOH-solution 2: aqueous sulfuric acid; sodium nitrite / Behandeln der Reaktionsloesung mit wss. Hypophosphorigsaeure 3: palladium/charcoal; ethanol / Hydrogenation 4: aqueous hydrobromic acid; sodium nitrite / Behandeln der Reaktionsloesung mit Kupfer(I)-bromid View Scheme |
3-Bromothiophenol
Bromoacetaldehyde diethyl acetal
A
6-bromobenzothiophene
B
4-bromobenzo[b]thiophene
Conditions | Yield |
---|---|
Stage #1: 3-Bromothiophenol; Bromoacetaldehyde diethyl acetal With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 24h; Stage #2: With PPA In 1,2-dichloro-ethane for 1h; Heating / reflux; |
1-bromo-3-[(2,2-dimethoxyethyl)sulfanyl]benzene
A
6-bromobenzothiophene
B
4-bromobenzo[b]thiophene
Conditions | Yield |
---|---|
With poliphosphoric acid In chlorobenzene for 2h; Product distribution / selectivity; Heating / reflux; | |
With PPA at 130℃; for 4.5 - 5.5h; Heating / reflux; | |
With PPA In chlorobenzene at 130℃; for 4.5 - 5.5h; Heating / reflux; | |
With PPA In chlorobenzene at 140℃; for 5.5h; Heating / reflux; | |
With phenylpropanol amine In chlorobenzene for 12h; Reflux; Overall yield = 91 %; Overall yield = 7 g; |
1-bromo-3-(2,2-diethoxy-ethylsulfanyl)benzene
A
6-bromobenzothiophene
B
4-bromobenzo[b]thiophene
Conditions | Yield |
---|---|
With PPA In 1,2-dichloro-ethane for 1h; Heating / reflux; | |
With sodium carbonate In dichloromethane for 4h; Reflux; Overall yield = 58 %; Overall yield = 0.33 g; |
3,6-dibromo-2-fluorobenzaldehyde
4-bromobenzo[b]thiophene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 7 h / -30 °C / Inert atmosphere 2.1: potassium carbonate / methanol / 2 h / 0 - 20 °C / Inert atmosphere 3.1: gold(I) chloride / 1,4-dioxane; water / 0.17 h / 20 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 4.2: -78 °C View Scheme |
3,6-dibromo-2-(t-butylsulfanyl)(ethynyl)benzene
4-bromobenzo[b]thiophene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: gold(I) chloride / 1,4-dioxane; water / 0.17 h / 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.2: -78 °C View Scheme |
3,6-dibromo-2-(t-butylsulfanyl)benzaldehyde
4-bromobenzo[b]thiophene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: potassium carbonate / methanol / 2 h / 0 - 20 °C / Inert atmosphere 2.1: gold(I) chloride / 1,4-dioxane; water / 0.17 h / 20 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 3.2: -78 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: phenylpropanol amine / chlorobenzene / 12 h / Reflux View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C 2: sodium carbonate / dichloromethane / 4 h / Reflux View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide / dimethyl sulfoxide; water 2: chlorobenzene View Scheme | |
Multi-step reaction with 2 steps 1.1: potassium hydroxide / water; dimethyl sulfoxide / 120 h / 20 °C 2.1: PPA / chlorobenzene / 1 h / 130 °C 2.2: 20 °C View Scheme |
2,6-dibromobenzaldehyde
4-bromobenzo[b]thiophene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: copper View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1.5 h / -78 °C / Inert atmosphere 1.2: 0.33 h / -78 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide / 60 °C / Inert atmosphere 3.1: sodium hydroxide / water; tetrahydrofuran / 1 h / 70 °C 4.1: silver carbonate; acetic acid / dimethyl sulfoxide / 120 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide / 60 °C / Inert atmosphere 3.1: sodium hydroxide / water; tetrahydrofuran / 1 h / 70 °C 4.1: silver carbonate; acetic acid / dimethyl sulfoxide / 120 °C View Scheme |
2-bromo-6-fluorobenzaldehyde
4-bromobenzo[b]thiophene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 60 °C / Inert atmosphere 2: sodium hydroxide / water; tetrahydrofuran / 1 h / 70 °C 3: silver carbonate; acetic acid / dimethyl sulfoxide / 120 °C View Scheme | |
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 4 h / 30 - 35 °C 2: toluene / 4 h / 110 °C 3: sodium hydride / tetrahydrofuran / 2 h / 20 - 30 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: sodium hydroxide / N,N-dimethyl-formamide / 2 h / 10 - 15 °C 2: toluene / 4 h / 110 °C 3: sodium hydride / tetrahydrofuran / 2 h / 20 - 30 °C / Inert atmosphere View Scheme |
4-bromobenzo[b]thiophene-2-carboxylic acid ethyl ester
4-bromobenzo[b]thiophene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / water; tetrahydrofuran / 1 h / 70 °C 2: silver carbonate; acetic acid / dimethyl sulfoxide / 120 °C View Scheme |
4-bromobenzo[b]thiophene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: toluene / 4 h / 110 °C 2: sodium hydride / tetrahydrofuran / 2 h / 20 - 30 °C / Inert atmosphere View Scheme |
4-bromobenzo[b]thiophene
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 20 - 30℃; for 2h; Solvent; Wittig Olefination; Inert atmosphere; |
Conditions | Yield |
---|---|
With phosphazene base-P4-tert-butyl In 1,4-dioxane at 80℃; for 21h; | 6 %Spectr. |
Conditions | Yield |
---|---|
With potassium phosphate; copper(l) iodide; 1,10-Phenanthroline In toluene at 100℃; for 24h; Solvent; Reagent/catalyst; Inert atmosphere; | 97.2% |
4-bromobenzo[b]thiophene
chloro-trimethyl-silane
7-bromo-2-trimethylsilyl-benzothiophene
Conditions | Yield |
---|---|
Stage #1: 4-bromobenzo[b]thiophene; chloro-trimethyl-silane With lithium diisopropyl amide In tetrahydrofuran; n-heptane at -70℃; for 1.53333h; Stage #2: With hydrogenchloride In tetrahydrofuran; n-heptane at -70℃; for 1.5h; | 95% |
Conditions | Yield |
---|---|
With 1,1,1,3',3',3'-hexafluoro-propanol; sodium acetate; palladium diacetate; silver(l) oxide at 30℃; for 16h; regioselective reaction; | 86% |
methanol
4-bromobenzo[b]thiophene
carbon monoxide
methyl benzothiophen-4-carboxylate
Conditions | Yield |
---|---|
With triethylamine; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate In dimethyl sulfoxide at 80℃; for 24h; | 84% |
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine at 120℃; Inert atmosphere; | 44% |
Conditions | Yield |
---|---|
With copper(l) iodide; potassium carbonate; L-proline In N,N-dimethyl-formamide at 110℃; for 10h; Reagent/catalyst; Solvent; Inert atmosphere; | 80.54% |
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl In toluene for 1h; Heating / reflux; | |
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate |
4-bromobenzo[b]thiophene
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In acetonitrile at 60℃; for 12h; | 80% |
Conditions | Yield |
---|---|
Stage #1: piperazine; 4-bromobenzo[b]thiophene With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 1h; Reflux; Inert atmosphere; Stage #2: With hydrogenchloride In methanol | 79.79% |
4-bromobenzo[b]thiophene
Brexpiprazole
Conditions | Yield |
---|---|
Stage #1: 7-[4-(piperazin-1-yl)butoxy]-2(1H)-quinolinone With trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) In dichloromethane; dimethyl sulfoxide at 25 - 35℃; for 0.25h; Inert atmosphere; Stage #2: 4-bromobenzo[b]thiophene In dichloromethane; dimethyl sulfoxide at 140 - 150℃; | 77.8% |
With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In 1,4-dioxane at 25 - 115℃; for 15h; Temperature; Inert atmosphere; | 40 g |
Conditions | Yield |
---|---|
With zinc(II) fluoride; tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide; toluene at 85℃; for 18h; Sealed tube; Inert atmosphere; | 75% |
Conditions | Yield |
---|---|
Stage #1: 4-bromobenzo[b]thiophene With iodine; magnesium In tetrahydrofuran at 50 - 55℃; for 1.5h; Stage #2: carbon dioxide In tetrahydrofuran at 23℃; for 0.25 - 0.333333h; Stage #3: With hydrogenchloride; water In tetrahydrofuran at 0℃; | 74% |
With manganese; 2.9-dimethyl-1,10-phenanthroline; lithium acetate; cobalt(II) bromide In N,N-dimethyl acetamide at 20℃; under 760.051 Torr; for 12h; Inert atmosphere; Schlenk technique; | 62% |
4-bromobenzo[b]thiophene
formamide
benzo[b]thiophene-4-carbonitrile
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; aluminum (III) chloride; nickel(II) acetylacetonate; zinc(II) oxide In 1,2-dimethoxyethane at 145℃; for 12h; | 72% |
4-bromobenzo[b]thiophene
(3‑methylbenzyl)(4‑methylphenyl) sulfide
Conditions | Yield |
---|---|
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(l) oxide; Trimethylacetic acid In dichloromethane at 100℃; for 24h; Inert atmosphere; Schlenk technique; | 72% |
Conditions | Yield |
---|---|
Stage #1: 4-bromobenzo[b]thiophene With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Stage #2: methyl iodide In tetrahydrofuran at -78℃; for 1h; | 71% |
Conditions | Yield |
---|---|
Stage #1: 4-bromobenzo[b]thiophene; ethyl 2-cyanoacetate With potassium phosphate; N-(2-methylnaphthalen-1-yl)-N’-(pyridin-2-ylmethyl)oxalamide; copper(l) chloride In ethanol at 80℃; for 24h; Schlenk technique; Inert atmosphere; Stage #2: With water In ethanol at 80℃; Schlenk technique; Inert atmosphere; Cooling; | 71% |
4-bromobenzo[b]thiophene
4-bromo-3-iodobenzo[b]thiophene
Conditions | Yield |
---|---|
With iodine In nitromethane at 120℃; for 1h; Sealed tube; regioselective reaction; | 69% |
4-bromobenzo[b]thiophene
bis(pinacol)diborane
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In diethylene glycol dimethyl ether at 80℃; Inert atmosphere; Sealed tube; | 60% |
4-bromobenzo[b]thiophene
1-t-Butoxycarbonylpiperazine
Conditions | Yield |
---|---|
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In N,N-dimethyl-formamide at 110℃; for 14h; Reagent/catalyst; Solvent; Inert atmosphere; | 55.37% |
4-bromobenzo[b]thiophene
benzo[b]thiophen-4-ylboronic acid
Conditions | Yield |
---|---|
With n-butyllithium; Triisopropyl borate In tetrahydrofuran at -78℃; | 49% |
Conditions | Yield |
---|---|
With tetrabutyl-ammonium chloride; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 100℃; Inert atmosphere; | 49% |
6-bromobenzothiophene
4-bromobenzo[b]thiophene
dicyanozinc
A
benzo[b]thiophene-6-carbonitrile
B
benzo[b]thiophene-4-carbonitrile
Conditions | Yield |
---|---|
tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 90 - 100℃; for 3h; | A 46.2% B 23% |
tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 90 - 100℃; for 3h; | A 46.2% B 23% |
4-bromobenzo[b]thiophene
N-tert-butyloxycarbonylpiperidin-4-one
1-(tert-butoxycarbonyl)-4-hydroxy-4-(benzothien-4-yl)piperidine
Conditions | Yield |
---|---|
Stage #1: 4-bromobenzo[b]thiophene With magnesium In tetrahydrofuran at 60℃; for 0.0833333h; Inert atmosphere; Stage #2: N-tert-butyloxycarbonylpiperidin-4-one In tetrahydrofuran at 20℃; for 1h; Further stages; | 44% |
4-bromobenzo[b]thiophene
(2-oxo-2-phenylethyl)triphenylphosphonium trifluoroacetate
Conditions | Yield |
---|---|
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cesium acetate; silver(l) oxide In 2,2,2-trifluoroethanol at 120℃; for 24h; Schlenk technique; Inert atmosphere; | 42% |
6-bromobenzothiophene
4-bromobenzo[b]thiophene
copper(I) cyanide
A
benzo[b]thiophene-6-carbonitrile
B
benzo[b]thiophene-4-carbonitrile
Conditions | Yield |
---|---|
With pyridine In N,N-dimethyl-formamide for 20h; Product distribution / selectivity; Heating / reflux; | A 41% B 39% |
Conditions | Yield |
---|---|
With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; potassium acetate; silver fluoride In tert-butyl alcohol at 100℃; for 24h; Schlenk technique; | 37% |
4-bromobenzo[b]thiophene
acrylic acid methyl ester
Conditions | Yield |
---|---|
With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate In water; acetonitrile at 50℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation; diastereoselective reaction; | 35% |
4-bromobenzo[b]thiophene
3-chloro-4-fluorophenylamine
molybdenum hexacarbonyl
Conditions | Yield |
---|---|
With palladium diacetate; sodium carbonate; tri tert-butylphosphoniumtetrafluoroborate In acetonitrile at 70℃; for 1h; Inert atmosphere; Microwave irradiation; | 32% |
4-bromobenzo[b]thiophene
2,5-dibromo-terephthalic acid diethyl ester
tributyltin chloride
tris-(o-tolyl)phosphine
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide | 31% |
The CAS register number of Benzo[b]thiophene,4-bromo- is 5118-13-8. It also can be called as 4-Bromobenzo[b]thiophene and the systematic name about this chemical is 4-bromo-1-benzothiophene. The molecular formula about this chemical is C8H5BrS and the molecular weight is 213.0943. It belongs to the following product categories which include Benzothiophene; Halogenated; Organohalides and so on. This chemical is irritant. It may cause inflammation to the skin or other mucous membranes.
Physical properties about Benzo[b]thiophene,4-bromo- are: (1)ACD/LogP: 3.96; (2)ACD/LogD (pH 5.5): 5; (3)ACD/LogD (pH 7.4): 5; (4)ACD/BCF (pH 5.5): 4845; (5)ACD/BCF (pH 7.4): 4845; (6)ACD/KOC (pH 5.5): 15119; (7)ACD/KOC (pH 7.4): 15119; (8)Polar Surface Area: 28.24 Å2; (9)Index of Refraction: 1.704; (10)Molar Refractivity: 50.17 cm3; (11)Molar Volume: 129.214 cm3; (12)Polarizability: 19.889x10-24cm3; (13)Surface Tension: 50.681 dyne/cm; (14)Density: 1.649 g/cm3; (15)Flash Point: 125.99 °C; (16)Enthalpy of Vaporization: 50.269 kJ/mol; (17)Boiling Point: 284.713 °C at 760 mmHg; (18)Vapour Pressure: 0.005 mmHg at 25 °C.
You can still convert the following datas into molecular structure:
(1)SMILES: Brc2cccc1sccc12;
(2)InChI: InChI=1/C8H5BrS/c9-7-2-1-3-8-6(7)4-5-10-8/h1-5H
(3)InChIKey: QPBSEYFVZDMBFW-UHFFFAOYAD
(4)Std. InChI: InChI=1S/C8H5BrS/c9-7-2-1-3-8-6(7)4-5-10-8/h1-5H
(5)Std. InChIKey: QPBSEYFVZDMBFW-UHFFFAOYSA-N
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