160096-76-4

Basic information

• Product Name: 2-Bromo-5-iodo-3-hexylthiophene
• Synonyms: 2-Bromo-5-iodo-3-hexylthiophene;2-Bromo-3-hexyl-5-iodothiophene;2-BroMo-3-hexyl-5-iodothiophene (stabilized with Copper chip);2-bromo-3-n-hexyl-5-iodothiophene
• CAS NO: 160096-76-4
• Molecular Formula: C₁₀H₁₄BrIS
• Molecular Weight: 373.09
• Mol File: 160096-76-4.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 121°C/0.6mmHg(lit.)
• Appearance: /
• Density: 1.727
• Refractive Index: 1.5880-1.5920
• Storage Temp.: <0°C
• CAS DataBase Reference: 2-Bromo-5-iodo-3-hexylthiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-5-iodo-3-hexylthiophene(160096-76-4)
• EPA Substance Registry System: 2-Bromo-5-iodo-3-hexylthiophene(160096-76-4)

Safety Data

• Hazardous Substances Data: 160096-76-4(Hazardous Substances Data)

Usage

Uses

2-Bromo-3-hexyl-5-iodothiophene is used as a reactant in the synthesis of structurally defined cationic polythiophenes for DNA binding and gene delivery.

Synthetic route

3-hexyl-2-bromothiophene (69249-61-2) → 2-bromo-5-iodo-3-hexylthiophene (160096-76-4)

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 (116971-11-0) → 2-bromo-5-iodo-3-hexylthiophene (160096-76-4)

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 (1693-86-3) → 2-bromo-5-iodo-3-hexylthiophene (160096-76-4)

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 (3761-92-0) → 2-bromo-5-iodo-3-hexylthiophene (160096-76-4)

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 (111-25-1) → 2-bromo-5-iodo-3-hexylthiophene (160096-76-4)

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 (1408285-51-7) + 2-bromo-5-iodo-3-hexylthiophene (160096-76-4) → 2-(3'-n-hexyl-5'-bromo[2,2'-bithiophen]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1452670-63-1)

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 (850881-09-3) + 2-bromo-5-iodo-3-hexylthiophene (160096-76-4) → 5’-bromo-3,4’-dihexyl-2,2’-bithiophene (154717-21-2)

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 (160096-76-4) + pyridin-2-ylzinc(II) bromide → 2-(4-bromo-3-hexylthien-2-yl)pyridine (1189375-66-3)

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 (871-84-1) + 2-bromo-5-iodo-3-hexylthiophene (160096-76-4) → 1,8-bis(5-bromo-4-hexylthiophen-2-yl)octa-1,7-diyne

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 (160096-76-4) → poly(3-hexylthiophene), Mn 17000, Mw/Mn 1.28 by GPC; monomer(s): 2-bromo-3-hexyl-5-iodothiophene

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%

C18H19B2F2N3O2 + 2-bromo-5-iodo-3-hexylthiophene (160096-76-4) → C22H21BBrF2N3S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 80℃; for 18h; Suzuki Coupling; Inert atmosphere;	77%

1-hexyl-2-(tributylstannyl)-1H-pyrrole + 2-bromo-5-iodo-3-hexylthiophene (160096-76-4) → 2-(5-bromo-4-hexylthiophen-2-yl)-1-hexyl-1H-pyrrole

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 (160096-76-4) → head-to-tail Br-poly(3-hexylthiophene), Mn 9300, Mw/Mn 1.10; monomer(s): 2-bromo-3-hexyl-5-iodothiophene

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%

C37H30B2F2N4O3S + 2-bromo-5-iodo-3-hexylthiophene (160096-76-4) → C41H32BBrF2N4OS2

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 (308795-91-7) + 2-bromo-5-iodo-3-hexylthiophene (160096-76-4) → C16H20BrNS (1227833-65-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	41%

2-bromo-5-iodo-3-hexylthiophene (160096-76-4) + 5’-bromo-3,4’-dihexyl-2,2’-bithiophene (154717-21-2) → 2-bromo-5-(5-(3-hexylthiophen-2-yl)-3-hexylthiophen-2-yl)-3-hexylthiophene (850881-10-6)

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 (160096-76-4) → 5-bromo-4,4'-dihexyl-2,2'-bithiophene (291273-95-5)

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;

2-bromo-5-iodo-3-hexylthiophene (160096-76-4) + (PPh3)2Ni(Ph)Br → polymer, polymerization at 0 deg C, end groups H, monomer(s): bromobenzene; 2-bromo-3-hexyl-5-iodothiophene + polymer, polymerization at 0 deg C, end groups Ph and Br, monomer(s): bromobenzene; 2-bromo-3-hexyl-5-iodothiophene + polymer, polymerization at 0 deg C, end groups Ph and H, monomer(s): bromobenzene; 2-bromo-3-hexyl-5-iodothiophene

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.

2-bromo-5-iodo-3-hexylthiophene (160096-76-4) + (PPh3)2Ni(Ph)Br → polymer, polymerization at RT, end groups Ph and Br, monomer(s): bromobenzene; 2-bromo-3-hexyl-5-iodothiophene + polymer, polymerization at RT, end groups Ph and H, monomer(s): bromobenzene; 2-bromo-3-hexyl-5-iodothiophene + polymer, polymerization at RT, end groups H, monomer(s): 2-bromo-3-hexyl-5-iodothiophene

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 (160096-76-4) + (PPh3)2Ni(o-Tol)Br → polymer, polymerization at 0 deg C, polymerization time 10 min, end groups Ph and Br, monomer(s): o-bromotoluene; 2-bromo-3-hexyl-5-iodothiophene + polymer, polymerization at 0 deg C, polymerization time 10 min, end groups Ph and H, monomer(s): o-bromotoluene; 2-bromo-3-hexyl-5-iodothiophene

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 (160096-76-4) + (PPh3)2Ni(o-Tol)Br → polymer, polymerization at 0 deg C, polymerization time 155 min, end groups Ph and Br, monomer(s): o-bromotoluene; 2-bromo-3-hexyl-5-iodothiophene + polymer, polymerization at 0 deg C, polymerization time 155 min, end groups Ph and H, monomer(s): o-bromotoluene; 2-bromo-3-hexyl-5-iodothiophene

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 (160096-76-4) + (PPh3)2Ni(o-Tol)Br → polymer, Mn = 3600, Mw/Mn = 1.78, monomer(s): o-bromotoluene; 2-bromo-3-hexyl-5-iodothiophene

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 (160096-76-4) + (PPh3)2Ni(o-Tol)Br → polymer, Mn = 4300, Mw/Mn = 1.91, monomer(s): o-bromotoluene; 2-bromo-3-hexyl-5-iodothiophene

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 (160096-76-4) → 5-(4,3'-dihexyl-2,2'-bithienyl-5-yl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane (850881-12-8)

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 (160096-76-4) → 2-bromo-5-(5-(3-hexylthiophen-2-yl)-3-hexylthiophen-2-yl)-3-hexylthiophene (850881-10-6)

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 (160096-76-4) → 5-([N-(2,6-diisopropylphenyl)]-9-perylenyl-3,4-dicarboximide)-4,3'-dihexyl-2,2'-bithiophene (850881-13-9)

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 (160096-76-4) → 5-([N-(2,6-diisopropylphenyl)]-9-perylenyl-3,4-dicarboximide)-4,3',3''-trihexyl-2,2';5',2''-terthiophene

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 (160096-76-4) → (5-bromo-4-hexylthiophen-2-yl)magnesium chloride (671775-27-2)

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;

Upstream product

• 111-25-1 1-bromo-hexane 
• 116971-11-0 2,5-dibromo-3-hexylthiophene 
• 69249-61-2 3-hexyl-2-bromothiophene 
• 3761-92-0 n-hexylmagnesium bromide 
• 1693-86-3 3-hexylthiophene 

Downstream Products

• 69249-61-2 3-hexyl-2-bromothiophene 
• 1207276-07-0 C₁₆H₁₉BrS 
• 1227627-75-9 C₂₆H₃₃BrS₂ 
• 1227627-76-0 C₃₆H₄₇BrS₃ 
• 850881-13-9 5-([N-(2,6-diisopropylphenyl)]-9-perylenyl-3,4-dicarboximide)-4,3'-dihexyl-2,2'-bithiophene 

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