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160096-76-4

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CAS No.: 160096-76-4
Name: 2-Bromo-5-iodo-3-hexylthiophene
Article Data: 17
Molecular Structure:
Molecular Structure of 160096-76-4 (2-Bromo-5-iodo-3-hexylthiophene)
Formula: C10H14BrIS
Molecular Weight: 373.096
Synonyms: 2-Bromo-3-hexyl-5-iodo-thiophene;
Density: 1.727
Boiling Point: 121°C/0.6mmHg(lit.)
PSA: 28.24000
LogP: 5.23800
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Synthetic route
69249-61-2

3-hexyl-2-bromothiophene

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%
116971-11-0

2,5-dibromo-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.;
1693-86-3

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
3761-92-0

n-hexylmagnesium bromide

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
111-25-1

1-bromo-hexane

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
1408285-51-7

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

160096-76-4

2-bromo-5-iodo-3-hexylthiophene

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%
850881-09-3

3-hexylthiophene-2-boronic acid pinacol ester

160096-76-4

2-bromo-5-iodo-3-hexylthiophene

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%
160096-76-4

2-bromo-5-iodo-3-hexylthiophene

pyridin-2-ylzinc(II) bromide

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%
871-84-1

1,7-Octadiyne

160096-76-4

2-bromo-5-iodo-3-hexylthiophene

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%
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%
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  • Thiophene,2-bromo-3-hexyl-5-iodo-

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  • 2-Bromo-5-iodo-3-hexylthiophene

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    2-Bromo-5-iodo-3-hexylthiophene

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Chemistry

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 

Specification

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