3-hexyl-2-bromothiophene
2-bromo-5-iodo-3-hexylthiophene
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene; iodine In dichloromethane at 20℃; for 4h; | 97% |
With N-iodo-succinimide In chloroform; acetic acid at 20℃; for 16h; Darkness; | 89% |
With N-iodo-succinimide; toluene-4-sulfonic acid In ethanol at 22 - 50℃; for 0.416667h; | 89% |
2,5-dibromo-3-hexylthiophene
2-bromo-5-iodo-3-hexylthiophene
Conditions | Yield |
---|---|
Stage #1: 2,5-dibromo-3-hexylthiophene With tetrabutylammonium tetrafluoroborate; zinc dibromide; (2,2'-bipyridine)nickel(II) dibromide In N,N-dimethyl-formamide at -10.16℃; Electrolysis; Stage #2: With iodine In N,N-dimethyl-formamide Further stages.; |
3-hexylthiophene
2-bromo-5-iodo-3-hexylthiophene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 95 percent / tetrabutylammonium bromide; methanol; Br2 / CH2Cl2 / 20 °C 2.1: ZnBr2; tetrabutylammonium tetrafluoroborate / NiBr2 2,2'-bipyridine / dimethylformamide / -10.16 °C / Electrolysis 2.2: I2 / dimethylformamide View Scheme | |
Multi-step reaction with 2 steps 1: 95 percent / N-bromosuccinimide / tetrahydrofuran / 1 h / 0 °C 2: 97 percent / I2; iodobenzene diacetate / CH2Cl2 / 4 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / tetrahydrofuran 2: iodine; [bis(acetoxy)iodo]benzene / tetrahydrofuran View Scheme |
n-hexylmagnesium bromide
2-bromo-5-iodo-3-hexylthiophene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: diethyl ether 2.1: 95 percent / tetrabutylammonium bromide; methanol; Br2 / CH2Cl2 / 20 °C 3.1: ZnBr2; tetrabutylammonium tetrafluoroborate / NiBr2 2,2'-bipyridine / dimethylformamide / -10.16 °C / Electrolysis 3.2: I2 / dimethylformamide View Scheme |
1-bromo-hexane
2-bromo-5-iodo-3-hexylthiophene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: magnesium / diethyl ether / 3.25 h / 20 °C / Inert atmosphere; Cooling with ice 1.2: 24 h / Inert atmosphere 2.1: N-Bromosuccinimide / tetrahydrofuran / 1 h / 0 °C 3.1: [bis(acetoxy)iodo]benzene; iodine / dichloromethane / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: magnesium / diethyl ether / 1 h / Reflux; Inert atmosphere 1.2: Reflux; Inert atmosphere 2.1: N-Bromosuccinimide / dichloromethane / Darkness; Inert atmosphere 3.1: iodine; [bis(acetoxy)iodo]benzene / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere; Darkness View Scheme |
4,4,5,5-tetramethyl-2-(5-(trimethylstannyl)thiophen-2-yl)-1,3,2-dioxaborolane
2-bromo-5-iodo-3-hexylthiophene
2-(3'-n-hexyl-5'-bromo[2,2'-bithiophen]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 100℃; for 0.333333h; Solvent; Reagent/catalyst; Concentration; Temperature; Time; Stille Cross Coupling; Microwave irradiation; | 95% |
3-hexylthiophene-2-boronic acid pinacol ester
2-bromo-5-iodo-3-hexylthiophene
5’-bromo-3,4’-dihexyl-2,2’-bithiophene
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane for 24h; Heating; | 90% |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In Dimethyl ether; water for 24h; Reflux; | 90% |
2-bromo-5-iodo-3-hexylthiophene
2-(4-bromo-3-hexylthien-2-yl)pyridine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; | 89% |
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; | 89% |
1,7-Octadiyne
2-bromo-5-iodo-3-hexylthiophene
Conditions | Yield |
---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In N,N-dimethyl-formamide at 55℃; for 21h; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique; | 84% |
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In 1,2-dimethoxyethane at 55℃; for 22h; | 73% |
2-bromo-5-iodo-3-hexylthiophene
Conditions | Yield |
---|---|
Stage #1: 2-bromo-5-iodo-3-hexylthiophene With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: With Cl2Ni(1,3-bis(diphenylphosphino)propane)2 In tetrahydrofuran at 20℃; for 24h; | 78% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 80℃; for 18h; Suzuki Coupling; Inert atmosphere; | 77% |
2-bromo-5-iodo-3-hexylthiophene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 70℃; for 32h; Stille Cross Coupling; Inert atmosphere; | 76% |
2-bromo-5-iodo-3-hexylthiophene
Conditions | Yield |
---|---|
Stage #1: 2-bromo-5-iodo-3-hexylthiophene With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 1h; Stage #2: With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran at 20℃; for 6h; | 72% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 80℃; for 18h; Suzuki Coupling; Inert atmosphere; | 71% |
3-methyl-pyridin-2-ylzinc bromide
2-bromo-5-iodo-3-hexylthiophene
C16H20BrNS
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; | 41% |
2-bromo-5-iodo-3-hexylthiophene
5’-bromo-3,4’-dihexyl-2,2’-bithiophene
2-bromo-5-(5-(3-hexylthiophen-2-yl)-3-hexylthiophen-2-yl)-3-hexylthiophene
Conditions | Yield |
---|---|
Stage #1: 5’-bromo-3,4’-dihexyl-2,2’-bithiophene With n-butyllithium In tetrahydrofuran; hexane at -80℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; hexane at -80 - 20℃; Stage #3: 2-bromo-5-iodo-3-hexylthiophene; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; hexane at 20℃; for 24h; Negishi cross-coupling; | 38% |
Stage #1: 5’-bromo-3,4’-dihexyl-2,2’-bithiophene With n-butyllithium In tetrahydrofuran at -80℃; for 1h; Stage #2: 2-bromo-5-iodo-3-hexylthiophene With zinc(II) chloride In tetrahydrofuran at 20℃; for 24h; | 38% |
2-bromo-5-iodo-3-hexylthiophene
5-bromo-4,4'-dihexyl-2,2'-bithiophene
Conditions | Yield |
---|---|
Stage #1: 2-bromo-5-iodo-3-hexylthiophene With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 1h; Stage #2: With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran at 20℃; for 1h; |
Conditions | Yield |
---|---|
Stage #1: 2-bromo-5-iodo-3-hexylthiophene With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 1h; Stage #2: (PPh3)2Ni(Ph)Br In tetrahydrofuran; toluene at 0℃; for 6h; Further stages. Title compound not separated from byproducts.; | A 2 % Spectr. B 20 % Spectr. C 78 % Spectr. |
Conditions | Yield |
---|---|
Stage #1: 2-bromo-5-iodo-3-hexylthiophene With tert-butylmagnesium chloride In tetrahydrofuran Stage #2: (PPh3)2Ni(Ph)Br In tetrahydrofuran; toluene at 20℃; for 4h; Further stages. Title compound not separated from byproducts.; | A 13 % Spectr. B 67 % Spectr. C 20 % Spectr. |
2-bromo-5-iodo-3-hexylthiophene
Conditions | Yield |
---|---|
Stage #1: 2-bromo-5-iodo-3-hexylthiophene With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 1h; Stage #2: (PPh3)2Ni(o-Tol)Br In tetrahydrofuran; toluene at 0℃; for 0.166667h; Further stages. Title compound not separated from byproducts.; |
2-bromo-5-iodo-3-hexylthiophene
Conditions | Yield |
---|---|
Stage #1: 2-bromo-5-iodo-3-hexylthiophene With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 1h; Stage #2: (PPh3)2Ni(o-Tol)Br In tetrahydrofuran; toluene at 0℃; for 2.58333h; Further stages. Title compound not separated from byproducts.; |
2-bromo-5-iodo-3-hexylthiophene
Conditions | Yield |
---|---|
Stage #1: 2-bromo-5-iodo-3-hexylthiophene With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 1h; Stage #2: (PPh3)2Ni(o-Tol)Br In tetrahydrofuran; toluene at 0℃; for 1.58333h; Further stages.; |
2-bromo-5-iodo-3-hexylthiophene
Conditions | Yield |
---|---|
Stage #1: 2-bromo-5-iodo-3-hexylthiophene With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 1h; Stage #2: (PPh3)2Ni(o-Tol)Br In tetrahydrofuran; toluene at 0℃; for 2.08333h; Further stages.; |
2-bromo-5-iodo-3-hexylthiophene
5-(4,3'-dihexyl-2,2'-bithienyl-5-yl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 90 percent / aq. NaHCO3 / [Pd(PPh3)4] / 1,2-dimethoxy-ethane / 24 h / Heating 2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -80 °C 2.2: tri(isopropyl)borate / tetrahydrofuran; hexane / -78 - 20 °C 2.3: tetrahydrofuran; hexane / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; Dimethyl ether / 24 h / Reflux 2.1: n-butyllithium / tetrahydrofuran / 0.5 h 2.2: 24 h / 20 °C View Scheme |
2-bromo-5-iodo-3-hexylthiophene
2-bromo-5-(5-(3-hexylthiophen-2-yl)-3-hexylthiophen-2-yl)-3-hexylthiophene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 90 percent / aq. NaHCO3 / [Pd(PPh3)4] / 1,2-dimethoxy-ethane / 24 h / Heating 2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -80 °C 2.2: ZnCl2 / tetrahydrofuran; hexane / -80 - 20 °C 2.3: 38 percent / [Pd(PPh3)4] / tetrahydrofuran; hexane / 24 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; Dimethyl ether / 24 h / Reflux 2.1: n-butyllithium / tetrahydrofuran / 1 h / -80 °C 2.2: 24 h / 20 °C View Scheme |
2-bromo-5-iodo-3-hexylthiophene
5-([N-(2,6-diisopropylphenyl)]-9-perylenyl-3,4-dicarboximide)-4,3'-dihexyl-2,2'-bithiophene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 90 percent / aq. NaHCO3 / [Pd(PPh3)4] / 1,2-dimethoxy-ethane / 24 h / Heating 2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -80 °C 2.2: tri(isopropyl)borate / tetrahydrofuran; hexane / -78 - 20 °C 2.3: tetrahydrofuran; hexane / 20 °C 3.1: 90 percent / aq. tripotassium phosphate / [Pd(PPh3)4] / 1,2-dimethoxy-ethane / 3 h / 80 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: 90 percent / aq. NaHCO3 / [Pd(PPh3)4] / 1,2-dimethoxy-ethane / 24 h / Heating 2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -80 °C 2.2: ZnCl2 / tetrahydrofuran; hexane / -80 - 20 °C 2.3: 76 percent / [Pd(PPh3)4] / tetrahydrofuran; hexane / 24 h / 65 °C View Scheme |
2-bromo-5-iodo-3-hexylthiophene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 90 percent / aq. NaHCO3 / [Pd(PPh3)4] / 1,2-dimethoxy-ethane / 24 h / Heating 2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -80 °C 2.2: ZnCl2 / tetrahydrofuran; hexane / -80 - 20 °C 2.3: 38 percent / [Pd(PPh3)4] / tetrahydrofuran; hexane / 24 h / 20 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -80 °C 3.2: ZnCl2 / tetrahydrofuran; hexane / -80 - 20 °C 3.3: 35 percent / [Pd(PPh3)4] / tetrahydrofuran; hexane / 24 h / 65 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -80 °C 1.2: ZnCl2 / tetrahydrofuran; hexane / -80 - 20 °C 1.3: 38 percent / [Pd(PPh3)4] / tetrahydrofuran; hexane / 24 h / 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -80 °C 2.2: ZnCl2 / tetrahydrofuran; hexane / -80 - 20 °C 2.3: 35 percent / [Pd(PPh3)4] / tetrahydrofuran; hexane / 24 h / 65 °C View Scheme |
2-bromo-5-iodo-3-hexylthiophene
(5-bromo-4-hexylthiophen-2-yl)magnesium chloride
Conditions | Yield |
---|---|
With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 1h; | |
With isopropylmagnesium chloride In tetrahydrofuran at 20℃; for 1h; | |
With isopropylmagnesium chloride | |
Stage #1: 2-bromo-5-iodo-3-hexylthiophene With TurboGrignard In tetrahydrofuran at 40℃; for 0.25h; Inert atmosphere; Stage #2: In tetrahydrofuran at 20℃; for 0.75h; Inert atmosphere; |
Molecular Structure of 2-Bromo-3-hexyl-5-iodothiophene (CAS No.160096-76-4):
Molecular Formula: C10H14BrIS
Molecular Weight: 373.0916
CAS No: 160096-76-4
H bond acceptors: 0
H bond donors: 0
Freely Rotating Bonds: 5
Polar Surface Area: 28.24 Å2
Index of Refraction: 1.594
Molar Refractivity: 73.315 cm3
Molar Volume: 216.015 cm3
Surface Tension: 42.725 dyne/cm
Density: 1.727 g/cm3
Flash Point: 157.131 °C
Enthalpy of Vaporization: 55.638 kJ/mol
Boiling Point: 336.205 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25°C
InChI: InChI=1/C10H14BrIS/c1-2-3-4-5-6-8-7-9(12)13-10(8)11/h7H,2-6H2,1H3
InChIKey: SDMKEQYHISDGKT-UHFFFAOYAP
Std. InChI: InChI=1S/C10H14BrIS/c1-2-3-4-5-6-8-7-9(12)13-10(8)11/h7H,2-6H2,1H3
Std. InChIKey: SDMKEQYHISDGKT-UHFFFAOYSA-N
Systematic Name: 2-Bromo-3-hexyl-5-iodothiophene
2-Bromo-3-hexyl-5-iodothiophene (CAS No.160096-76-4), its synonym is 2-Bromo-5-iodo-3-hexylthiophene .
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