Product Name

  • Name

    2-Bromo-5-iodo-3-hexylthiophene

  • EINECS
  • CAS No. 160096-76-4
  • Article Data17
  • CAS DataBase
  • Density 1.727
  • Solubility
  • Melting Point
  • Formula C10H14BrIS
  • Boiling Point 121°C/0.6mmHg(lit.)
  • Molecular Weight 373.096
  • Flash Point
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 160096-76-4 (2-Bromo-5-iodo-3-hexylthiophene)
  • Hazard Symbols
  • Synonyms 2-Bromo-3-hexyl-5-iodo-thiophene;
  • PSA 28.24000
  • LogP 5.23800

Synthetic route

3-hexyl-2-bromothiophene
69249-61-2

3-hexyl-2-bromothiophene

2-bromo-5-iodo-3-hexylthiophene
160096-76-4

2-bromo-5-iodo-3-hexylthiophene

Conditions
ConditionsYield
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

2,5-dibromo-3-hexylthiophene

2-bromo-5-iodo-3-hexylthiophene
160096-76-4

2-bromo-5-iodo-3-hexylthiophene

Conditions
ConditionsYield
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

3-hexylthiophene

2-bromo-5-iodo-3-hexylthiophene
160096-76-4

2-bromo-5-iodo-3-hexylthiophene

Conditions
ConditionsYield
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

n-hexylmagnesium bromide

2-bromo-5-iodo-3-hexylthiophene
160096-76-4

2-bromo-5-iodo-3-hexylthiophene

Conditions
ConditionsYield
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

1-bromo-hexane

2-bromo-5-iodo-3-hexylthiophene
160096-76-4

2-bromo-5-iodo-3-hexylthiophene

Conditions
ConditionsYield
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

4,4,5,5-tetramethyl-2-(5-(trimethylstannyl)thiophen-2-yl)-1,3,2-dioxaborolane

2-bromo-5-iodo-3-hexylthiophene
160096-76-4

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
1452670-63-1

2-(3'-n-hexyl-5'-bromo[2,2'-bithiophen]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
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

3-hexylthiophene-2-boronic acid pinacol ester

2-bromo-5-iodo-3-hexylthiophene
160096-76-4

2-bromo-5-iodo-3-hexylthiophene

5’-bromo-3,4’-dihexyl-2,2’-bithiophene
154717-21-2

5’-bromo-3,4’-dihexyl-2,2’-bithiophene

Conditions
ConditionsYield
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

2-bromo-5-iodo-3-hexylthiophene

pyridin-2-ylzinc(II) bromide

pyridin-2-ylzinc(II) bromide

2-(4-bromo-3-hexylthien-2-yl)pyridine
1189375-66-3

2-(4-bromo-3-hexylthien-2-yl)pyridine

Conditions
ConditionsYield
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

1,7-Octadiyne

2-bromo-5-iodo-3-hexylthiophene
160096-76-4

2-bromo-5-iodo-3-hexylthiophene

1,8-bis(5-bromo-4-hexylthiophen-2-yl)octa-1,7-diyne

1,8-bis(5-bromo-4-hexylthiophen-2-yl)octa-1,7-diyne

Conditions
ConditionsYield
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

2-bromo-5-iodo-3-hexylthiophene

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

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

Conditions
ConditionsYield
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

C18H19B2F2N3O2

2-bromo-5-iodo-3-hexylthiophene
160096-76-4

2-bromo-5-iodo-3-hexylthiophene

C22H21BBrF2N3S

C22H21BBrF2N3S

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 80℃; for 18h; Suzuki Coupling; Inert atmosphere;77%
1-hexyl-2-(tributylstannyl)-1H-pyrrole

1-hexyl-2-(tributylstannyl)-1H-pyrrole

2-bromo-5-iodo-3-hexylthiophene
160096-76-4

2-bromo-5-iodo-3-hexylthiophene

2-(5-bromo-4-hexylthiophen-2-yl)-1-hexyl-1H-pyrrole

2-(5-bromo-4-hexylthiophen-2-yl)-1-hexyl-1H-pyrrole

Conditions
ConditionsYield
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

2-bromo-5-iodo-3-hexylthiophene

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

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

Conditions
ConditionsYield
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

C37H30B2F2N4O3S

2-bromo-5-iodo-3-hexylthiophene
160096-76-4

2-bromo-5-iodo-3-hexylthiophene

C41H32BBrF2N4OS2

C41H32BBrF2N4OS2

Conditions
ConditionsYield
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

3-methyl-pyridin-2-ylzinc bromide

2-bromo-5-iodo-3-hexylthiophene
160096-76-4

2-bromo-5-iodo-3-hexylthiophene

C16H20BrNS
1227833-65-9

C16H20BrNS

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;41%
2-bromo-5-iodo-3-hexylthiophene
160096-76-4

2-bromo-5-iodo-3-hexylthiophene

5’-bromo-3,4’-dihexyl-2,2’-bithiophene
154717-21-2

5’-bromo-3,4’-dihexyl-2,2’-bithiophene

2-bromo-5-(5-(3-hexylthiophen-2-yl)-3-hexylthiophen-2-yl)-3-hexylthiophene
850881-10-6

2-bromo-5-(5-(3-hexylthiophen-2-yl)-3-hexylthiophen-2-yl)-3-hexylthiophene

Conditions
ConditionsYield
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

2-bromo-5-iodo-3-hexylthiophene

5-bromo-4,4'-dihexyl-2,2'-bithiophene
291273-95-5

5-bromo-4,4'-dihexyl-2,2'-bithiophene

Conditions
ConditionsYield
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

2-bromo-5-iodo-3-hexylthiophene

(PPh3)2Ni(Ph)Br

(PPh3)2Ni(Ph)Br

A

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 H, monomer(s): bromobenzene; 2-bromo-3-hexyl-5-iodothiophene

B

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 Br, monomer(s): bromobenzene; 2-bromo-3-hexyl-5-iodothiophene

C

polymer, polymerization at 0 deg C, end groups Ph and H, 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
ConditionsYield
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

2-bromo-5-iodo-3-hexylthiophene

(PPh3)2Ni(Ph)Br

(PPh3)2Ni(Ph)Br

A

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 Br, monomer(s): bromobenzene; 2-bromo-3-hexyl-5-iodothiophene

B

polymer, polymerization at RT, end groups Ph and H, 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

C

polymer, polymerization at RT, end groups H, monomer(s): 2-bromo-3-hexyl-5-iodothiophene

polymer, polymerization at RT, end groups H, monomer(s): 2-bromo-3-hexyl-5-iodothiophene

Conditions
ConditionsYield
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

2-bromo-5-iodo-3-hexylthiophene

(PPh3)2Ni(o-Tol)Br

(PPh3)2Ni(o-Tol)Br

A

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 Br, monomer(s): o-bromotoluene; 2-bromo-3-hexyl-5-iodothiophene

B

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

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
ConditionsYield
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

2-bromo-5-iodo-3-hexylthiophene

(PPh3)2Ni(o-Tol)Br

(PPh3)2Ni(o-Tol)Br

A

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 Br, monomer(s): o-bromotoluene; 2-bromo-3-hexyl-5-iodothiophene

B

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

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
ConditionsYield
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

2-bromo-5-iodo-3-hexylthiophene

(PPh3)2Ni(o-Tol)Br

(PPh3)2Ni(o-Tol)Br

polymer, Mn = 3600, Mw/Mn = 1.78, monomer(s): o-bromotoluene; 2-bromo-3-hexyl-5-iodothiophene

polymer, Mn = 3600, Mw/Mn = 1.78, monomer(s): o-bromotoluene; 2-bromo-3-hexyl-5-iodothiophene

Conditions
ConditionsYield
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

2-bromo-5-iodo-3-hexylthiophene

(PPh3)2Ni(o-Tol)Br

(PPh3)2Ni(o-Tol)Br

polymer, Mn = 4300, Mw/Mn = 1.91, monomer(s): o-bromotoluene; 2-bromo-3-hexyl-5-iodothiophene

polymer, Mn = 4300, Mw/Mn = 1.91, monomer(s): o-bromotoluene; 2-bromo-3-hexyl-5-iodothiophene

Conditions
ConditionsYield
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

2-bromo-5-iodo-3-hexylthiophene

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

5-(4,3'-dihexyl-2,2'-bithienyl-5-yl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane

Conditions
ConditionsYield
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-iodo-3-hexylthiophene

2-bromo-5-(5-(3-hexylthiophen-2-yl)-3-hexylthiophen-2-yl)-3-hexylthiophene
850881-10-6

2-bromo-5-(5-(3-hexylthiophen-2-yl)-3-hexylthiophen-2-yl)-3-hexylthiophene

Conditions
ConditionsYield
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

2-bromo-5-iodo-3-hexylthiophene

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

5-([N-(2,6-diisopropylphenyl)]-9-perylenyl-3,4-dicarboximide)-4,3'-dihexyl-2,2'-bithiophene

Conditions
ConditionsYield
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

2-bromo-5-iodo-3-hexylthiophene

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

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

Conditions
ConditionsYield
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

2-bromo-5-iodo-3-hexylthiophene

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

(5-bromo-4-hexylthiophen-2-yl)magnesium chloride

Conditions
ConditionsYield
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;

2-Bromo-3-hexyl-5-iodothiophene Chemical Properties

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 Specification

   2-Bromo-3-hexyl-5-iodothiophene (CAS No.160096-76-4), its synonym is 2-Bromo-5-iodo-3-hexylthiophene .

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