3437-95-4

Basic information

• Product Name: 2-Iodothiophene
• Synonyms: 2-IODTHIOPHENE;2-THIENYL IODIDE;2-iodo-thiophen;2-Iodothyophene;alpha-Iodothiophene;thiophene,2-iodo-;2-Iodothiophene, 98+%;2-IODOTHIOPHENE , STABILIZED WITH COPPER
• CAS NO: 3437-95-4
• Molecular Formula: C₄H₃IS
• Molecular Weight: 210.04
• EINECS: 222-342-1
• Product Categories: Thiophenes;Sulphur Derivatives;Halides;Thiophenes & Benzothiophenes;Thiophene&Benzothiophene;Thiophenes & Benzothiophenes;Halogenated Heterocycles;Heterocyclic Building Blocks;ThiophenesBuilding Blocks;Heterocycle-oher series;alkyl Iodine
• Mol File: 3437-95-4.mol
• Article Data: 46

Chemical Properties

• Melting Point: −40 °C(lit.)
• Boiling Point: 73 °C15 mm Hg(lit.)
• Flash Point: 160 °F
• Appearance: Clear yellow-green to red-brown/Liquid
• Density: 1.902 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.14mmHg at 25°C
• Refractive Index: n20/D 1.651(lit.)
• Storage Temp.: 0-6°C
• Sensitive: Light Sensitive
• BRN: 104666
• CAS DataBase Reference: 2-Iodothiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Iodothiophene(3437-95-4)
• EPA Substance Registry System: 2-Iodothiophene(3437-95-4)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41-43-20/21/22-36/37/38
• Safety Statements: 26-36/37/39-36/37-27
• WGK Germany: 3
• F: 3
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 3437-95-4(Hazardous Substances Data)

Usage

Chemical Properties

colorless to light yellow liquid

Uses

2-Iodothiophene was used in the synthesis of (E)-and (Z)-2,3-difluoro-3-aryl substituted acrylic esters. It was also used as monomer in the preparation of thin conductive films via plasma polymerization of 2-iodothiophene.

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 4883, 1995 DOI: 10.1016/0040-4039(95)00876-E

General Description

Mechanism of the fluoride-free, palladium-catalyzed cross-coupling reaction of 2-iodothiophene with potassium (E)-heptenyldimethylsilanolate has been investigated. 2-Iodothiophene participates in microwave-enhanced, rapid homogeneous-phase version of the Sonogashira reaction.

InChI:InChI=1/C4H3IS/c5-4-2-1-3-6-4/h1-3H

Synthetic route

thiophene boronic acid (6165-68-0) → 2-Iodothiophene (3437-95-4)

Conditions	Yield
With potassium fluoride; iodine In 1,4-dioxane at 80℃; for 1h;	93%
With N-iodo-succinimide In acetonitrile at 25℃; for 14h;	72%

thiophene (188290-36-0) → 2-Iodothiophene (3437-95-4)

Conditions	Yield
With N-iodosaccharine at 20℃; Ionic liquid; Darkness;	92%
Stage #1: thiophene With n-butyllithium; magnesium bromide In tetrahydrofuran at 20℃; for 2h; Stage #2: With iodine In tetrahydrofuran at 20℃; for 18h;	90%
With iodine; bis-[(trifluoroacetoxy)iodo]benzene In tetrachloromethane for 2h;	83%

[(tmeda)Na(μ-C4H3S)3Mg(tmeda)] → 2-Iodothiophene (3437-95-4)

Conditions	Yield
With iodine In tetrahydrofuran; hexane at 20℃; for 18h; Inert atmosphere;	86%

di-[2]thienyl-mercury (5980-89-2) → 2-Iodothiophene (3437-95-4)

Conditions	Yield
With iodine; potassium iodide at 80℃; for 0.5h;	65%

thiophene (188290-36-0) → 2-Iodothiophene (3437-95-4) + 2,5-diiodothiophene (625-88-7)

Conditions	Yield
With potassium iodate; sulfuric acid; iodine In tetrachloromethane; water at 66℃; for 3h;	A 59.6% B 4.3%
Stage #1: thiophene With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; dichloro(N,N,N’,N‘-tetramethylethylenediamine)zinc In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane Inert atmosphere;	A 54% B 32%
With potassium dichloroiodate monohydrate In dichloromethane at 25℃; for 6h;	A 20 %Chromat. B 30%

2-thiophenylcarboxylic acid (527-72-0) → 2-Iodothiophene (3437-95-4)

Conditions	Yield
With N-iodo-succinimide; [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; iodine; caesium carbonate In acetonitrile at 50℃; for 24h; Inert atmosphere; Irradiation; Sealed tube;	57%

thiophene (188290-36-0) + cyanogen iodide (506-78-5) → 2-Iodothiophene (3437-95-4)

Conditions	Yield
at 100℃;
at 100℃;

diethyl ether (60-29-7) + cyanogen iodide (506-78-5) + [2]thienyl magnesium (1+); bromide → 2-bromothiophene (1003-09-4) + 2-Iodothiophene (3437-95-4)

phenyl-[2]thienyl-iodonium ; iodide (41018-48-8) → 2-Iodothiophene (3437-95-4) + iodobenzene (591-50-4)

Conditions	Yield
Erhitzen bis auf 160grad;

di-2-thienyliodonium iodide (29393-21-3) → 2-Iodothiophene (3437-95-4)

Conditions	Yield
Erhitzen auf 120grad;

2-bromothiophene (1003-09-4) → 2-Iodothiophene (3437-95-4)

Conditions	Yield
With potassium iodide; nickel dibromide In various solvent(s) at 90℃; for 1h; electrolysis; Yield given;
With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 110℃; for 20h;
Stage #1: 2-bromothiophene With indium; bathophenanthroline; 3-chloroprop-1-ene; lithium chloride; cobalt(II) bromide In tetrahydrofuran at 80℃; for 18h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;	89 %Chromat.

thiophene (188290-36-0) → 2-thienyl chloride (96-43-5) + 2-Iodothiophene (3437-95-4) + 2-chloro-5-iodothiophene (28712-49-4) + 2,5-diiodothiophene (625-88-7)

Conditions	Yield
With N,N,N-trimethylbenzenemethanaminium dichloroiodate; zinc(II) chloride In acetic acid at 70℃; for 24h; Yield given. Yields of byproduct given;

thiophene (188290-36-0) + iodine (7553-56-2) + nitric acid (7697-37-2) → 2-Iodothiophene (3437-95-4)

<2>thienylmercury chloride → 2-Iodothiophene (3437-95-4)

Conditions	Yield
With iodine; potassium iodide

thiophene (188290-36-0) + iodine (7553-56-2) + mercury oxide → 2-Iodothiophene (3437-95-4) + 2,5-diiodothiophene (625-88-7)

water (7732-18-5) + phenyl(thiophen-2-yl)iodonium trifluoroacetate (6185-59-7) + sodium sulfite → 2-Iodothiophene (3437-95-4) + iodobenzene (591-50-4)

C11H10SOI(1+)*C2F3O2(1-) → 2-Iodothiophene (3437-95-4) + C6H3O2F3S + para-iodoanisole (696-62-8) + 4-methoxyphenyl trifluoroacetate (5672-87-7)

Conditions	Yield
With cesium fluoride

diethyl ether (60-29-7) → 2-Iodothiophene (3437-95-4)

bis(2-thienyl)iodonium hexafluorophosphate → thiophene (188290-36-0) + 2-fluorothiophene (400-13-5) + 2-Iodothiophene (3437-95-4)

Conditions	Yield
With potassium fluoride at 172 - 175℃; for 2h; neat (no solvent);

(thiene-2-yl)(4'-methoxyphenyl)iodonium trifluoracetate → 2-Iodothiophene (3437-95-4) + para-iodoanisole (696-62-8) + p-methoxy-phenylazide (2101-87-3)

Conditions	Yield
With tetrabutylammoniun azide In [D3]acetonitrile at 80℃; for 12h; Inert atmosphere; Darkness; regioselective reaction;	A n/a B n/a C 66 %Spectr.

(thiene-2-yl)(4'-methoxyphenyl)iodonium trifluoracetate + sodium 2,2,2-trifluoroethanolate (420-87-1) → 2-Iodothiophene (3437-95-4) + para-iodoanisole (696-62-8) + 1-(2,2,2-trifluoroethoxy)-4-methoxybenzene (62158-88-7) + 2-(2,2,2-trifluoroethoxy)thiophene (136019-61-9)

Conditions	Yield
In [D3]acetonitrile at 80℃; for 12h; Inert atmosphere; Darkness; regioselective reaction;	A n/a B n/a C 17 %Spectr. D 43 %Spectr.

(thiene-2-yl)(4'-methoxyphenyl)iodonium trifluoracetate + sodium phenoxide (139-02-6) → 2-Iodothiophene (3437-95-4) + para-iodoanisole (696-62-8) + 1-methoxy-4-phenoxy-benzene (1655-69-2) + 2-thienylphenyl ether (1235887-93-0)

Conditions	Yield
In [D3]acetonitrile at 80℃; for 12h; Inert atmosphere; Darkness; regioselective reaction;	A n/a B n/a C 69 %Spectr. D 23 %Spectr.

(thiene-2-yl)(4'-methoxyphenyl)iodonium trifluoracetate + tetrabutylammonium acetate (10534-59-5) → 2-Iodothiophene (3437-95-4) + para-iodoanisole (696-62-8) + 4-methoxyphenyl acetate (1200-06-2)

Conditions	Yield
In [D3]acetonitrile at 120℃; for 8h; Inert atmosphere; Darkness; regioselective reaction;	A n/a B n/a C 18 %Spectr.

(thiene-2-yl)(4'-methoxyphenyl)iodonium trifluoracetate + tetra-N-butylammonium benzenethiolate (4670-62-6) → 2-Iodothiophene (3437-95-4) + 2-(Phenylthio)thiophene (16718-12-0) + para-iodoanisole (696-62-8) + 1-methoxy-4-(phenylsulfanyl)benzene (5633-57-8)

Conditions	Yield
In [D3]acetonitrile at 80℃; for 12h; Inert atmosphere; Darkness; regioselective reaction;	A n/a B 40 %Spectr. C n/a D 30 %Spectr.

(thiene-2-yl)(4'-methoxyphenyl)iodonium trifluoracetate + tetrabutylammonium thiocyanate (3674-54-2) → 2-Iodothiophene (3437-95-4) + para-iodoanisole (696-62-8) + 4-thiocyanatoanisole (5285-90-5)

Conditions	Yield
In [D3]acetonitrile at 120℃; for 8h; Inert atmosphere; Darkness; regioselective reaction;	A n/a B n/a C 43 %Spectr.

2-thienyl chloride (96-43-5) → 2-Iodothiophene (3437-95-4)

Conditions	Yield
Stage #1: 2-thienyl chloride With indium; bathophenanthroline; 3-chloroprop-1-ene; lithium chloride; cobalt(II) bromide In tetrahydrofuran at 80 - 100℃; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;	64 %Chromat.
With sodium iodide In tetrahydrofuran; acetone at 25℃; for 3h; Solvent; Inert atmosphere; Darkness;	193.89 g

2,5-diiodothiophene (625-88-7) → 2-Iodothiophene (3437-95-4)

Conditions	Yield
With indium; 1-n-butyl-3-methylimidazolim bromide at 95℃; for 14h; Green chemistry;	> 99 %Chromat.

1-(thien-2-yl)ethanol (115510-91-3) → 2-Iodothiophene (3437-95-4)

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; oxygen; potassium carbonate In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 18h; Autoclave; Molecular sieve;	88 %Chromat.

2-Iodothiophene (3437-95-4) + trimethylsilylacetylene (1066-54-2) → 2-(trimethylsilylethynyl)thiophene (40231-03-6)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 2h;	100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; trimethylamine for 0.5h; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique; Reflux;	100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique;	99%

2-Iodothiophene (3437-95-4) + hex-1-yne (693-02-7) → 2-(hex-1-ynyl)thiophene (19482-59-8)

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 50℃;	100%
Stage #1: 2-Iodothiophene; hex-1-yne With bis-triphenylphosphine-palladium(II) chloride; triethylamine In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With copper(l) iodide In tetrahydrofuran at 20℃; Inert atmosphere;	93%
With triethylamine; palladium bis(2,2,6,6-tetramethyl-3,5-heptanedionate) In water at 20℃; for 6h; Sonogashira cross-coupling;	89%

2-Iodothiophene (3437-95-4) + phenylboronic acid (98-80-6) → 2-phenylthiophene (825-55-8)

Conditions	Yield
With Tedicyp; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)) In xylene at 130℃; for 20h; Suzuki cross-coupling reaction;	100%
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling;	99%
With caesium carbonate In water; N,N-dimethyl-formamide at 50℃; for 2h; Suzuki Coupling;	99%

2-Iodothiophene (3437-95-4) + Cyclopropylacetylene (6746-94-7) → 1-cyclopropyl-2-(thiophen-2-yl)acetylene (445424-06-6)

Conditions	Yield
With copper(l) iodide; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride In triethylamine at 25℃; for 16h; Sonogashira coupling;	100%
Stage #1: 2-Iodothiophene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triphenylphosphine In triethylamine at 25℃; for 0.5h; Sonogashira coupling; Inert atmosphere; Stage #2: Cyclopropylacetylene In triethylamine at 25℃; for 16h; Sonogashira coupling; Inert atmosphere;	85%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 20℃; for 16.5h;

2-Iodothiophene (3437-95-4) + dimethyl(hept-1-yn-1-yl)aluminum → 2-(hept-1-yn-1-yl)thiophene (64146-58-3)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,1'-bis-(diphenylphosphino)ferrocene In 1,2-dimethoxyethane; n-heptane at 20℃; for 3h;	100%

2-Iodothiophene (3437-95-4) + 2-pyrrolidinon (616-45-5) + argon. trans-1,2-Cyclohexanediamine + ethyl acetate n-hexane → 1-(thiophen-2-yl)pyrrolidin-2-one

Conditions	Yield
With potassium phosphate; CuI In 1,4-dioxane; dodecane; ethyl acetate	100%

2-Iodothiophene (3437-95-4) + C10H10OS → C14H12OS2

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 1h;	100%

2-Iodothiophene (3437-95-4) + 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) → 2-phenylthiophene (825-55-8)

Conditions	Yield
With potassium carbonate In methanol at 60℃; for 1h; Suzuki-Miyaura Coupling;	99.8%

2-Iodothiophene (3437-95-4) + phenylacetylene (536-74-3) → 2-(phenylethynyl)thiophene (4805-17-8)

Conditions	Yield
With copper(l) iodide; diisopropylamine; triphenylphosphine; silica gel; palladium at 85℃; for 18h; Sonogashira coupling;	99.3%
With 1,4-diaza-bicyclo[2.2.2]octane In water at 60℃; for 2h; Catalytic behavior; Sonogashira Cross-Coupling;	99%
With sodium hydroxide; palladium dichloride at 250℃; under 120012 Torr; for 2.77778E-05h; Sonogashira coupling;	98%

2-Iodothiophene (3437-95-4) + styrene (292638-84-7) → (E)-2-(2-phenylethenyl)thiophene (3783-65-1, 23516-73-6, 26708-50-9, 35568-97-9)

Conditions	Yield
With tributyl-amine In N,N-dimethyl-formamide at 120℃; for 4h; Heck-Mizoroki reaction; stereoselective reaction;	99%
Stage #1: 2-Iodothiophene With palladium diacetate; heptakis(6-amino-6-deoxy)-β-cyclodextrin In water; N,N-dimethyl-formamide for 0.5h; Stage #2: styrene With potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 10h;	89%
With triethylamine; nanostructured pyridine-functionalized silica Pd(II) complex In acetonitrile for 24h; Heck coupling; Heating;	84%

2-Iodothiophene (3437-95-4) + carbon monoxide (201230-82-2) + triphenylaluminium (841-76-9) → benzophenone (119-61-9) + 2-Benzoylthiophene (135-00-2)

Conditions	Yield
dichloro bis(acetonitrile) palladium(II) In dimethyl sulfoxide at 55℃; for 3h; Product distribution;	A 5% B 99%

2-Iodothiophene (3437-95-4) + carbon monoxide (201230-82-2) + triphenylaluminium etherate (58482-37-4) → benzophenone (119-61-9) + 2-Benzoylthiophene (135-00-2)

Conditions	Yield
dichloro bis(acetonitrile) palladium(II) In dimethyl sulfoxide at 55℃; under 760 Torr; for 3h;	A 5% B 99%

2-Iodothiophene (3437-95-4) + propargyl alcohol (107-19-7) → 3-thiophen-2-yl-prop-2-yn-1-ol (1194-13-4)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In water at 60℃; for 1h; Catalytic behavior; Sonogashira Cross-Coupling;	99%
With piperidine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In toluene at 20 - 35℃; for 17.5h; Inert atmosphere;	98%
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl acetamide at 50℃; for 24h; Sonogashira Cross-Coupling; Inert atmosphere;	98%

2-Iodothiophene (3437-95-4) + thiophene boronic acid (6165-68-0) → 2,2'-Bithiophene (492-97-7)

Conditions	Yield
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling;	99%
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In tetrahydrofuran; water for 24h; Suzuki cross-coupling; Inert atmosphere; Reflux;	60%
With sodium phosphate; poly(N-vinyl-2-pyrrolidone); palladium In ethanol; water for 48h; Suzuki cross-coupling reaction; Heating;	26%
With potassium fluoride In ethanol; water at 140℃; for 0.0333333h; Microwave irradiation;	100 %Chromat.

2-Iodothiophene (3437-95-4) + carbon monoxide (201230-82-2) + 4-Bu3Sn,2Cl-C6H3CONH-Rink resin → 2-chloro-4-(thiophene-2-carbonyl)-benzamide

Conditions	Yield
Stage #1: 2-Iodothiophene; carbon monoxide; 4-Bu3Sn,2Cl-C6H3CONH-Rink resin With tetrakis(triphenylphosphine) palladium(0) In dimethyl sulfoxide at 80℃; under 2068.59 Torr; for 18h; Stille coupling reaction; Stage #2: With trifluoroacetic acid In dichloromethane at 23℃; for 0.5h;	99%

2-Iodothiophene (3437-95-4) + 2-Methylphenylboronic acid (16419-60-6) → 2-(2-methylphenyl)thiophene (99846-56-7)

Conditions	Yield
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling;	99%
With potassium fluoride; palladium In methanol for 4h; Suzuki coupling reaction; Heating;	90%

2-Iodothiophene (3437-95-4) + 4-methylphenylboronic acid (5720-05-8) → 2-p-tolylthiophene (16939-04-1)

Conditions	Yield
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling;	99%
With potassium carbonate In ethanol; water at 80℃; for 6h; Suzuki Coupling;	96%
With (3aS,7aS)-1,3-di-o-tolyl-octahydro-benzoimidazole-2-thione; potassium carbonate; palladium(II) iodide In water; isopropyl alcohol at 80℃; for 5h; Suzuki reaction;	93%

2-Iodothiophene (3437-95-4) + benzo[b]thiophene-2-boronic acid (98437-23-1) → 2-(thiophene-2-yl)benzo[b]thiophene (55164-48-2)

Conditions	Yield
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling;	99%

2-Iodothiophene (3437-95-4) + (E)-1-hexenyldihydroxyborane (42599-18-8) → 2-hex-1-enyl-thiophene (73350-61-5)

Conditions	Yield
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling;	99%

2-Iodothiophene (3437-95-4) + thianthren-1-yl boronic acid (108847-76-3) → 1-thiophen-2-yl-thianthrene

Conditions	Yield
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling;	99%

2-Iodothiophene (3437-95-4) + m-tolylboronic acid (17933-03-8) → 2-(3-methylphenyl)thiophene (85553-43-1)

Conditions	Yield
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling;	99%

2-Iodothiophene (3437-95-4) + 4-Chlorophenylboronic acid (1679-18-1) → 2-(4-chlorophenyl)thiophene (40133-23-1)

Conditions	Yield
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling;	99%
With potassium carbonate In water; N,N-dimethyl-formamide at 100℃; under 2585.81 Torr; for 0.333333h; Suzuki reaction; Microwave irradiation;	92%
With potassium carbonate; Pd-N-heterocyclic carbene-organic silica In water; N,N-dimethyl-formamide at 100℃; for 0.16h; Suzuki reaction; microwave irradiation;	91 % Chromat.

2-Iodothiophene (3437-95-4) + 4-methoxyphenylboronic acid (5720-07-0) → 2-(4-methoxyphenyl)thiophene (42545-43-7)

Conditions	Yield
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling;	99%
With potassium carbonate In ethanol; water at 20℃; for 0.5h; Suzuki-Miyaura Coupling; Sealed tube; Green chemistry;	98%
With C17H23Br2N3Pd; potassium tert-butylate In water at 60℃; for 24h; Suzuki-Miyaura coupling reaction; Inert atmosphere;	96%

2-Iodothiophene (3437-95-4) + 1-Naphthylboronic acid (13922-41-3) → 1-(2-thienyl)naphthalene (4632-51-3)

Conditions	Yield
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling;	99%
With potassium carbonate In water at 25℃; for 3h; Suzuki-Miyaura Coupling;	92%

2-Iodothiophene (3437-95-4) + 4-trifluoromethylphenylboronic acid (128796-39-4) → 2-(4-(trifluoromethyl)phenyl)thiophene (115933-15-8)

Conditions	Yield
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling;	99%

Upstream product

• 188290-36-0 thiophene 
• 506-78-5 cyanogen iodide 
• 60-29-7 diethyl ether 
• 7553-56-2 iodine 
• 7732-18-5 water 
• 6185-59-7 phenyl(thiophen-2-yl)iodonium trifluoroacetate 
• 420-87-1 sodium 2,2,2-trifluoroethanolate 
• 139-02-6 sodium phenoxide 
• 10534-59-5 tetrabutylammonium acetate 
• 4670-62-6 tetra-N-butylammonium benzenethiolate 
• 3674-54-2 tetrabutylammonium thiocyanate 
• 527-72-0 2-thiophenylcarboxylic acid 
• 625-88-7 2,5-diiodothiophene 
• 96-43-5 2-thienyl chloride 

Downstream Products

• 98-03-3 thiophene-2-carbaldehyde 
• 5380-42-7 thiophene-2-carboxylic acid methyl ester 
• 26878-13-7 methyl 2-thienylglyoxylate 
• 3783-65-1 (E)-2-(2-phenylethenyl)thiophene 
• 4805-17-8 2-(phenylethynyl)thiophene 
• 55968-16-6 2-(2-thienyl)indole 
• 124643-51-2 2-[(thiophen-2-yl)ethynyl]phenylamine 
• 143746-69-4 2-(2-theonyl)-4,5-dichlorobenzoic acid 
• 16644-98-7 (E)-1-iodohexene 
• 80638-90-0 1,1-dimethoxy 2-(2 thienyl 3-methyl) 2(Z) pentene 
• 18764-73-3 N-acetyl-S-(2-thienyl)-L-cysteine 
• 188290-36-0 thiophene 
• 39511-07-4 (E)-2-(2-thienyl)ethylene-1-carbaldehyde 
• 492-97-7 2,2'-Bithiophene 

Relevant articles and documents

Efficient synthesis of 2-iodo and 2-dicyanomethyl derivatives of thiophene, selenophene, tellurophene, and thieno[3,2-b]thiophene

An effective synthesis of 2-iodothiophene, 2-iodotellurophene, and 2-iodothieno[3,2-b]thiophene and a Pd-catalyzed carbon-carbon coupling reaction of these iodo derivatives as well as 2-iodoselenophene with malononitrile affording novel thienyl-, tellurienyl-, thieno[3,2-b]thienyl-, and selenienybnalononitrile are described. These heteroarylmalononitriles are important synthons for the preparation of 2-dicyanomethylene-2,5-dihydroheterophene chromophores.

Sodium-mediated magnesiation of thiophene and tetrahydrothiophene: Structural contrasts with furan and tetrahydrofuran

Metallation of sulfur heterocycles; Alkali-metal-mediated magnesiation has been employed to regioselectively metallate the S-heterocycles thiophene and tetrahydrothiophene at ambient temperature. The structural chemistry of the metallo-compounds is remark

Copper-promoted cyanation of aryl iodides with N,N-dimethyl aminomalononitrile

A copper-promoted cyanation of aryl iodides has been successfully developed by using N,N-dimethyl aminomalononitrile as the cyanide source with moderate toxicity and better stability. This reaction features broad substrate scope, excellent reaction yields, readily available catalyst, and simple reaction conditions.

Orthogonal Stability and Reactivity of Aryl Germanes Enables Rapid and Selective (Multi)Halogenations

While halogenation is of key importance in synthesis and radioimaging, the currently available repertoire is largely designed to introduce a single halogen per molecule. This report makes the selective introduction of several different halogens accessible. Showcased here is the privileged stability of nontoxic aryl germanes under harsh fluorination conditions (that allow selective fluorination in their presence), while displaying superior reactivity and functional-group tolerance in electrophilic iodinations and brominations, outcompeting silanes or boronic esters under rapid and additive-free conditions. Mechanistic experiments and computational studies suggest a concerted electrophilic aromatic substitution as the underlying mechanism.