6964-21-2

Basic information

• Product Name: 3-Thiopheneacetic acid
• Synonyms: RARECHEM AL BO 0216;THIOPHENE-3-ACETIC ACID;THIEN-3-YLACETIC ACID;TIMTEC-BB SBB004147;3-THIENYLACETIC ACID;3-THIOPHENEACETIC ACID;Thiophene-3-aceticacid,98%;3-Thiopheneacetic
• CAS NO: 6964-21-2
• Molecular Formula: C₆H₆O₂S
• Molecular Weight: 142.18
• EINECS: 230-166-1
• Product Categories: Acids and Derivatives;Heterocycles;Thiophene&Benzothiophene;Heterocyclic Compounds;Thiophens;Functional Materials;Reagents for Conducting Polymer Research;Thiophene Derivatives (for Conduting Polymer Research)
• Mol File: 6964-21-2.mol
• Article Data: 13

Chemical Properties

• Melting Point: 73-76 °C(lit.)
• Boiling Point: 129°C 2,5mm
• Flash Point: 129°C/2.5mm
• Appearance: Off-white to beige/Crystalline Flakes or Powder
• Density: 1.365 (estimate)
• Vapor Pressure: 0.00265mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: Store below +30°C.
• PKA: 4.25±0.10(Predicted)
• Water Solubility: Very soluble in water.
• BRN: 113622
• CAS DataBase Reference: 3-Thiopheneacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Thiopheneacetic acid(6964-21-2)
• EPA Substance Registry System: 3-Thiopheneacetic acid(6964-21-2)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38-34
• Safety Statements: 26-24/25-45-36/37/39-27
• RIDADR: 1759
• WGK Germany: 3
• RTECS: XM7570000
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 6964-21-2(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

Different sources of media describe the Uses of 6964-21-2 differently. You can refer to the following data:
1. 3-Thiopheneacetic acid was used in one-step, size control synthesis of gold nanoparticles. It was also used in the preparation of gold nanoparticles capped with 3-thiopheneacetic acid (3-TAA) via borohydride reduction.
2. 3-Thiopheneacetic acid was used in:one-step, size control synthesis of gold nanoparticlesin the preparation of gold nanoparticles capped with 3-thiopheneacetic acid (3-TAA) via borohydride reduction

General Description

3-Thiopheneacetic acid acts as monocarboxylate ligand and forms oxo-carboxylate bridged digadolinium(III) complexes. Electrochemical oxidation of 3-thiopheneacetic acid in dry acetonitrile leads to the formation of a conducting polymeric film of poly (3-thiopheneacetic acid).

Purification Methods

Crystallise the acid from ligroin or H2O. [Beilstein 18 III/IV 4066.]

InChI:InChI=1/C6H6O2S/c7-6(8)3-5-1-2-9-4-5/h1-2,4H,3H2,(H,7,8)/p-1

Synthetic route

3-Bromomethylthiophene (34846-44-1) + carbon monoxide (201230-82-2) → thiophen-3-yl-acetic acid (6964-21-2)

Conditions	Yield
Stage #1: 3-Bromomethylthiophene; carbon monoxide With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium iodide at 80℃; under 760 Torr; for 18h; Carbonylation; Hydrolysis; Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 1h;	85%

carbon dioxide (124-38-9) + [1-Thiophen-3-yl-meth-(E)-ylidene]-hydrazine → thiophen-3-yl-acetic acid (6964-21-2)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; caesium carbonate; cesium fluoride In N,N-dimethyl-formamide at 80℃; under 760.051 Torr; for 24h; chemoselective reaction;	47%

3-hydroxymethyl-thiophene (71637-34-8) + carbon monoxide (201230-82-2) → thiophen-3-yl-acetic acid (6964-21-2) + 3-Methylthiophene (616-44-4)

Conditions	Yield
With hydrogen iodide; tetrakis(triphenylphosphine) palladium(0) In acetone at 90℃; under 68400 Torr; for 42h; Carbonylation; reduction;	A 34% B 11%
With tetrakis(triphenylphosphine) palladium(0); hydrogen iodide In acetone at 90℃; under 68400 Torr; for 42h;	A 34 % Spectr. B 11 % Spectr.

3-Bromomethylthiophene (34846-44-1) + sodium cyanide (143-33-9) → thiophen-3-yl-acetic acid (6964-21-2)

Conditions	Yield
With ethanol Erwaermen des Reaktionsprodukts mit aethanol. Kalilauge;

2-(thiophene-3-yl) acetamide (13781-66-3) → thiophen-3-yl-acetic acid (6964-21-2)

Conditions	Yield
With potassium hydroxide

ethyl-3 thiophene acetate (37784-63-7) → thiophen-3-yl-acetic acid (6964-21-2)

Conditions	Yield
With sodium hydroxide

3-thienyl iodide (10486-61-0) + tert-butyl sodioacetate → thiophen-3-yl-acetic acid (6964-21-2) + 2-acetoacetic acid (541-50-4) + Di-thiophen-3-yl-acetic acid

Conditions	Yield
With toluene-4-sulfonic acid; iron(II) sulfate 1.) NH3 (liquid), 45 min, 2.) H2O, reflux, 4 h; Yield given. Multistep reaction. Yields of byproduct given;

thiophen-3-yl-acetic acid i-propyl ester (53064-74-7) → thiophen-3-yl-acetic acid (6964-21-2) + propene (187737-37-7)

Conditions	Yield
In gaseous matrix at 326.9℃; gas-phase Hammett replacement ς0 substituent constant was investigated;

Thiophen-3-yl-acetic acid tert-butyl ester (58416-26-5) → thiophen-3-yl-acetic acid (6964-21-2) + isobutene (115-11-7)

Conditions	Yield
In gaseous matrix at 326.9℃; gas-phase Hammett replacement ς0 substituent constant was investigated;

1-diazo-2-(thiophen-3-yl)ethanone (124687-94-1) → thiophen-3-yl-acetic acid (6964-21-2)

Conditions	Yield
With silver(l) oxide In 1,4-dioxane Rearrangement;

3-thiophene carboxylic acid chloride (41507-35-1) → thiophen-3-yl-acetic acid (6964-21-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether / 0 °C 2: aq. Ag2O / dioxane View Scheme
Multi-step reaction with 2 steps 1: diethyl ether / Erwaermen des Reaktionsprodukts mit Silberoxid und Aethanol 2: ethanolic NaOH-solution View Scheme

3-Thiophene carboxylic acid (88-13-1) → thiophen-3-yl-acetic acid (6964-21-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: (COCl)2; DMF / CH2Cl2 2: diethyl ether / 0 °C 3: aq. Ag2O / dioxane View Scheme

methanol (67-56-1) + thiophen-3-yl-acetic acid (6964-21-2) → thiophen-3-yl-acetic acid methyl ester (58414-52-1)

Conditions	Yield
With hydrogenchloride for 3h; Heating;	100%
With sulfuric acid for 24h; Reflux;	100%
With acetyl chloride at 0 - 20℃;	100%

thiophen-3-yl-acetic acid (6964-21-2) → 2-(2-chlorothiophen-3-yl)acetic acid (188718-23-2)

Conditions	Yield
With N-chloro-succinimide; acetic acid In benzene at 80℃; for 1h; Inert atmosphere;	100%
With N-chloro-succinimide; acetic acid

thiophen-3-yl-acetic acid (6964-21-2) → 3-(2-hydroxyethyl)thiophene (13781-67-4)

Conditions	Yield
Stage #1: thiophen-3-yl-acetic acid With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 2h; Stage #2: With water In tetrahydrofuran; ethyl acetate	99%
With lithium aluminium tetrahydride	98%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 3h; Schlenk technique; Inert atmosphere;	98%

thiophen-3-yl-acetic acid (6964-21-2) + 5,6-dimethoxy-2-(N-propylamino)indan (162751-96-4) → N-(5,6-dimethoxy-indan-2-yl)-N-propyl-2-thiophen-3-yl-acetamide (745060-23-5)

Conditions	Yield
With diethyl cyanophosphonate; triethylamine In dichloromethane at 20℃; for 24h;	99%

thiophen-3-yl-acetic acid (6964-21-2) + benzylamine (100-46-9) → N-benzyl-2-(thiophen-3-yl)acetamide (940741-63-9)

Conditions	Yield
With zirconium(IV) chloride In tetrahydrofuran at 70℃; for 24h; Molecular sieve; Inert atmosphere;	99%
With tris(2,2,2-trifluoroethyl) borate In acetonitrile at 80℃; for 5h;	91%
Stage #1: thiophen-3-yl-acetic acid With titanium(IV) isopropylate In tetrahydrofuran at 40 - 70℃; Molecular sieve; Inert atmosphere; Stage #2: benzylamine In tetrahydrofuran at 70℃; Molecular sieve; Inert atmosphere;	88%

thiophen-3-yl-acetic acid (6964-21-2) + ethanol (64-17-5) → ethyl-3 thiophene acetate (37784-63-7)

Conditions	Yield
With hydrogenchloride for 0.166667h;	98%
With sulfuric acid for 24h; Reflux;	97%
With sulfuric acid for 24h; Reflux;	97%

thiophen-3-yl-acetic acid (6964-21-2) + 2-diazo-3-(3-ethyl-2-oxo-piperidin-3-yl)-3-oxo-propionic acid ethyl ester (786704-01-6) → 2-diazo-3-[3-ethyl-2-oxo-1-(2-thiophen-3-yl-acetyl)-piperidin-3-yl]-3-oxo-propionic acid ethyl ester (786704-15-2)

Conditions	Yield
Stage #1: thiophen-3-yl-acetic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 1h; Stage #2: 2-diazo-3-(3-ethyl-2-oxo-piperidin-3-yl)-3-oxo-propionic acid ethyl ester In tetrahydrofuran for 8h;	97%
Stage #1: thiophen-3-yl-acetic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide for 1h; Stage #2: 2-diazo-3-(3-ethyl-2-oxo-piperidin-3-yl)-3-oxo-propionic acid ethyl ester With 4 A molecular sieve In tetrahydrofuran for 9h;	97%

thiophen-3-yl-acetic acid (6964-21-2) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → N-methoxy-N-methyl-2-(thiophen-3-yl)acetamide (654682-77-6)

Conditions	Yield
Stage #1: thiophen-3-yl-acetic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at 20℃; for 60h; Inert atmosphere;	96%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;	95%
Stage #1: thiophen-3-yl-acetic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 1h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at 20℃; for 5h;	89%

thiophen-3-yl-acetic acid (6964-21-2) + butan-1-ol (71-36-3) → thiophen-3-yl-acetic acid n-butyl ester

Conditions	Yield
With sulfuric acid In benzene for 24h; Reflux;	96%
sulfuric acid for 6h; Heating;	60%

thiophen-3-yl-acetic acid (6964-21-2) → N-hydroxy-2-(thiophen-3-yl)acetamide (1013424-78-6)

Conditions	Yield
Stage #1: thiophen-3-yl-acetic acid With 4-(Methylamino)pyridine; diisopropyl-carbodiimide In dichloromethane at 20℃; Stage #2: With hydroxylamine In dichloromethane; water at 20℃; Further stages.;	96%

thiophen-3-yl-acetic acid (6964-21-2) → 2-(thiophen-3-yl)acetyl chloride (13781-65-2)

Conditions	Yield
With thionyl chloride at 60℃; for 2h;	95%
With sulfuryl dichloride at 60℃; for 3h;
With thionyl chloride for 3h; Heating;

thiophen-3-yl-acetic acid (6964-21-2) + (Z)-4-bromo-N′-hydroxybenzimidamide (19227-14-6) → O- p-bromobenzamidoxime

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane Ambient temperature;	95%

thiophen-3-yl-acetic acid (6964-21-2) + methyl chloroformate (79-22-1) → thiophen-3-yl-acetic acid methyl ester (58414-52-1)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 2h;	94%

thiophen-3-yl-acetic acid (6964-21-2) + 2,3,4,5,6-pentafluorophenol (771-61-9) → Pentafluorophenyl (thiophen-3-yl)ethanoate (214832-32-3)

Conditions	Yield
With dicyclohexyl-carbodiimide In 1,4-dioxane	92%

thiophen-3-yl-acetic acid (6964-21-2) + 2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → N-(3',4'-dimethoxy-β-phenethyl)-3-thienylacetamide (70474-53-2)

Conditions	Yield
at 170℃; Heating;	92%
for 2h; Heating;	92%
With triethylamine; HATU In dichloromethane at 20℃;

thiophen-3-yl-acetic acid (6964-21-2) + 2-chloro-ethanol (107-07-3) → thiophen-3-yl-acetic acid 2-chloro-ethyl ester (477282-74-9)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane	92%

thiophen-3-yl-acetic acid (6964-21-2) + Ethyl 4-bromobenzoate (5798-75-4) + methyl iodide (74-88-4) → C16H16O4S (1350637-88-5)

Conditions	Yield
Stage #1: thiophen-3-yl-acetic acid; Ethyl 4-bromobenzoate With palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 120℃; for 8h; Inert atmosphere; Stage #2: methyl iodide With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h; regioselective reaction;	92%

thiophen-3-yl-acetic acid (6964-21-2) + 4-bromobenzenecarbonitrile (623-00-7) + methyl iodide (74-88-4) → C14H11NO2S (1350637-89-6)

Conditions	Yield
Stage #1: thiophen-3-yl-acetic acid; 4-bromobenzenecarbonitrile With palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 120℃; for 8h; Inert atmosphere; Stage #2: methyl iodide With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h; regioselective reaction;	92%

thiophen-3-yl-acetic acid (6964-21-2) + 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (2564-83-2, 45842-10-2) + diazomethyl-trimethyl-silane (18107-18-1) → methyl 2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)-2-(thiophen-3-yl)acetate

Conditions

Yield

Stage #1: thiophen-3-yl-acetic acid; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical With N4,N4,N7,N7-tetramethyl-1,10-phenanthroline-4,7-diamine; iron(II) acetate In tetrahydrofuran at 60℃; for 24h; Molecular sieve; Inert atmosphere; Schlenk technique; Stage #2: diazomethyl-trimethyl-silane With methanol In tetrahydrofuran; hexane for 1h; Inert atmosphere; Stage #3: With acetic acid In tetrahydrofuran; hexane; ethyl acetate chemoselective reaction;

92%

thiophen-3-yl-acetic acid (6964-21-2) + ethyl iodide (75-03-6) + ortho-bromobenzaldehyde (6630-33-7) → C15H12O2S

Conditions	Yield
Stage #1: thiophen-3-yl-acetic acid; ortho-bromobenzaldehyde With palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl acetamide at 110℃; for 12h; Stage #2: ethyl iodide In N,N-dimethyl-formamide at 20℃; Reagent/catalyst; Temperature;	91%

thiophen-3-yl-acetic acid (6964-21-2) + ethyl bromide (74-96-4) + ortho-bromobenzaldehyde (6630-33-7) → C15H12O2S

Conditions	Yield
Stage #1: thiophen-3-yl-acetic acid; ortho-bromobenzaldehyde With palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl acetamide at 110℃; for 12h; Stage #2: ethyl bromide In N,N-dimethyl-formamide at 20℃;	91%

carbon dioxide (124-38-9) + 3-[(phenylsulfonyl)methyl]thiophene (129759-54-2) → thiophen-3-yl-acetic acid (6964-21-2)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 30℃; for 6h; Electrolysis;	99%

3-Bromomethylthiophene (34846-44-1) + carbon monoxide (201230-82-2) → thiophen-3-yl-acetic acid (6964-21-2)

Conditions	Yield
Stage #1: 3-Bromomethylthiophene; carbon monoxide With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium iodide at 80℃; under 760 Torr; for 18h; Carbonylation; Hydrolysis; Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 1h;	85%

carbon dioxide (124-38-9) + [1-Thiophen-3-yl-meth-(E)-ylidene]-hydrazine → thiophen-3-yl-acetic acid (6964-21-2)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; caesium carbonate; cesium fluoride In N,N-dimethyl-formamide at 80℃; under 760.051 Torr; for 24h; chemoselective reaction;	47%

3-hydroxymethyl-thiophene (71637-34-8) + carbon monoxide (201230-82-2) → thiophen-3-yl-acetic acid (6964-21-2) + 3-Methylthiophene (616-44-4)

Conditions	Yield
With hydrogen iodide; tetrakis(triphenylphosphine) palladium(0) In acetone at 90℃; under 68400 Torr; for 42h; Carbonylation; reduction;	A 34% B 11%
With tetrakis(triphenylphosphine) palladium(0); hydrogen iodide In acetone at 90℃; under 68400 Torr; for 42h;	A 34 % Spectr. B 11 % Spectr.

3-Bromomethylthiophene (34846-44-1) + sodium cyanide (143-33-9) → thiophen-3-yl-acetic acid (6964-21-2)

Conditions	Yield
With ethanol Erwaermen des Reaktionsprodukts mit aethanol. Kalilauge;

2-(thiophene-3-yl) acetamide (13781-66-3) → thiophen-3-yl-acetic acid (6964-21-2)

Conditions	Yield
With potassium hydroxide

ethyl-3 thiophene acetate (37784-63-7) → thiophen-3-yl-acetic acid (6964-21-2)

Conditions	Yield
With sodium hydroxide

3-thienyl iodide (10486-61-0) + tert-butyl sodioacetate → thiophen-3-yl-acetic acid (6964-21-2) + 2-acetoacetic acid (541-50-4) + Di-thiophen-3-yl-acetic acid

Conditions	Yield
With toluene-4-sulfonic acid; iron(II) sulfate 1.) NH3 (liquid), 45 min, 2.) H2O, reflux, 4 h; Yield given. Multistep reaction. Yields of byproduct given;

thiophen-3-yl-acetic acid i-propyl ester (53064-74-7) → thiophen-3-yl-acetic acid (6964-21-2) + propene (187737-37-7)

Conditions	Yield
In gaseous matrix at 326.9℃; gas-phase Hammett replacement ς0 substituent constant was investigated;

Thiophen-3-yl-acetic acid tert-butyl ester (58416-26-5) → thiophen-3-yl-acetic acid (6964-21-2) + isobutene (115-11-7)

Conditions	Yield
In gaseous matrix at 326.9℃; gas-phase Hammett replacement ς0 substituent constant was investigated;

1-diazo-2-(thiophen-3-yl)ethanone (124687-94-1) → thiophen-3-yl-acetic acid (6964-21-2)

Conditions	Yield
With silver(l) oxide In 1,4-dioxane Rearrangement;

3-thiophene carboxylic acid chloride (41507-35-1) → thiophen-3-yl-acetic acid (6964-21-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether / 0 °C 2: aq. Ag2O / dioxane View Scheme
Multi-step reaction with 2 steps 1: diethyl ether / Erwaermen des Reaktionsprodukts mit Silberoxid und Aethanol 2: ethanolic NaOH-solution View Scheme

3-Thiophene carboxylic acid (88-13-1) → thiophen-3-yl-acetic acid (6964-21-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: (COCl)2; DMF / CH2Cl2 2: diethyl ether / 0 °C 3: aq. Ag2O / dioxane View Scheme

methanol (67-56-1) + thiophen-3-yl-acetic acid (6964-21-2) → thiophen-3-yl-acetic acid methyl ester (58414-52-1)

Conditions	Yield
With hydrogenchloride for 3h; Heating;	100%
With sulfuric acid for 24h; Reflux;	100%
With acetyl chloride at 0 - 20℃;	100%

thiophen-3-yl-acetic acid (6964-21-2) → 2-(2-chlorothiophen-3-yl)acetic acid (188718-23-2)

Conditions	Yield
With N-chloro-succinimide; acetic acid In benzene at 80℃; for 1h; Inert atmosphere;	100%
With N-chloro-succinimide; acetic acid

thiophen-3-yl-acetic acid (6964-21-2) → 3-(2-hydroxyethyl)thiophene (13781-67-4)

Conditions	Yield
Stage #1: thiophen-3-yl-acetic acid With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 2h; Stage #2: With water In tetrahydrofuran; ethyl acetate	99%
With lithium aluminium tetrahydride	98%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 3h; Schlenk technique; Inert atmosphere;	98%

thiophen-3-yl-acetic acid (6964-21-2) + 5,6-dimethoxy-2-(N-propylamino)indan (162751-96-4) → N-(5,6-dimethoxy-indan-2-yl)-N-propyl-2-thiophen-3-yl-acetamide (745060-23-5)

Conditions	Yield
With diethyl cyanophosphonate; triethylamine In dichloromethane at 20℃; for 24h;	99%

thiophen-3-yl-acetic acid (6964-21-2) + benzylamine (100-46-9) → N-benzyl-2-(thiophen-3-yl)acetamide (940741-63-9)

Conditions	Yield
With zirconium(IV) chloride In tetrahydrofuran at 70℃; for 24h; Molecular sieve; Inert atmosphere;	99%
With tris(2,2,2-trifluoroethyl) borate In acetonitrile at 80℃; for 5h;	91%
Stage #1: thiophen-3-yl-acetic acid With titanium(IV) isopropylate In tetrahydrofuran at 40 - 70℃; Molecular sieve; Inert atmosphere; Stage #2: benzylamine In tetrahydrofuran at 70℃; Molecular sieve; Inert atmosphere;	88%

thiophen-3-yl-acetic acid (6964-21-2) + ethanol (64-17-5) → ethyl-3 thiophene acetate (37784-63-7)

Conditions	Yield
With hydrogenchloride for 0.166667h;	98%
With sulfuric acid for 24h; Reflux;	97%
With sulfuric acid for 24h; Reflux;	97%

thiophen-3-yl-acetic acid (6964-21-2) + 2-diazo-3-(3-ethyl-2-oxo-piperidin-3-yl)-3-oxo-propionic acid ethyl ester (786704-01-6) → 2-diazo-3-[3-ethyl-2-oxo-1-(2-thiophen-3-yl-acetyl)-piperidin-3-yl]-3-oxo-propionic acid ethyl ester (786704-15-2)

Conditions	Yield
Stage #1: thiophen-3-yl-acetic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 1h; Stage #2: 2-diazo-3-(3-ethyl-2-oxo-piperidin-3-yl)-3-oxo-propionic acid ethyl ester In tetrahydrofuran for 8h;	97%
Stage #1: thiophen-3-yl-acetic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide for 1h; Stage #2: 2-diazo-3-(3-ethyl-2-oxo-piperidin-3-yl)-3-oxo-propionic acid ethyl ester With 4 A molecular sieve In tetrahydrofuran for 9h;	97%

thiophen-3-yl-acetic acid (6964-21-2) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → N-methoxy-N-methyl-2-(thiophen-3-yl)acetamide (654682-77-6)

Conditions	Yield
Stage #1: thiophen-3-yl-acetic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at 20℃; for 60h; Inert atmosphere;	96%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;	95%
Stage #1: thiophen-3-yl-acetic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 1h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at 20℃; for 5h;	89%

thiophen-3-yl-acetic acid (6964-21-2) + butan-1-ol (71-36-3) → thiophen-3-yl-acetic acid n-butyl ester

Conditions	Yield
With sulfuric acid In benzene for 24h; Reflux;	96%
sulfuric acid for 6h; Heating;	60%

thiophen-3-yl-acetic acid (6964-21-2) → N-hydroxy-2-(thiophen-3-yl)acetamide (1013424-78-6)

Conditions	Yield
Stage #1: thiophen-3-yl-acetic acid With 4-(Methylamino)pyridine; diisopropyl-carbodiimide In dichloromethane at 20℃; Stage #2: With hydroxylamine In dichloromethane; water at 20℃; Further stages.;	96%

thiophen-3-yl-acetic acid (6964-21-2) → 2-(thiophen-3-yl)acetyl chloride (13781-65-2)

Conditions	Yield
With thionyl chloride at 60℃; for 2h;	95%
With sulfuryl dichloride at 60℃; for 3h;
With thionyl chloride for 3h; Heating;

thiophen-3-yl-acetic acid (6964-21-2) + (Z)-4-bromo-N′-hydroxybenzimidamide (19227-14-6) → O- p-bromobenzamidoxime

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane Ambient temperature;	95%

thiophen-3-yl-acetic acid (6964-21-2) + ortho-bromobenzaldehyde (6630-33-7) → naphtho[1,2-b]thiophene-4-carboxylic acid (50920-15-5)

Conditions	Yield
With palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl acetamide at 110℃; for 12h;	95%
With palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 110℃; for 12h; Inert atmosphere; regiospecific reaction;	95%

thiophen-3-yl-acetic acid (6964-21-2) + N,N-dimethylethylenediamine (108-00-9) → N-(2-(dimethylamino)ethyl)-2-(thiophene-3-yl)acetamide

Conditions	Yield
With boric acid In toluene for 24h; Reflux;	94.92%
Stage #1: thiophen-3-yl-acetic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 0℃; for 0.333333h; Inert atmosphere; Stage #2: N,N-dimethylethylenediamine In tetrahydrofuran at 20℃;	67%

Upstream product

• 34846-44-1 3-Bromomethylthiophene 
• 143-33-9 sodium cyanide 
• 124687-94-1 1-diazo-2-(thiophen-3-yl)ethanone 
• 201230-82-2 carbon monoxide 
• 124-38-9 carbon dioxide 
• 129759-54-2 3-[(phenylsulfonyl)methyl]thiophene 
• 88-13-1 3-Thiophene carboxylic acid 
• 41507-35-1 3-thiophene carboxylic acid chloride 
• 71637-34-8 3-hydroxymethyl-thiophene 
• 58416-26-5 Thiophen-3-yl-acetic acid tert-butyl ester 
• 53064-74-7 thiophen-3-yl-acetic acid i-propyl ester 
• 10486-61-0 3-thienyl iodide 
• 37784-63-7 ethyl-3 thiophene acetate 
• 13781-66-3 2-(thiophene-3-yl) acetamide 

Downstream Products

• 58414-52-1 thiophen-3-yl-acetic acid methyl ester 
• 70474-57-6 N-(4-benzyloxy-3-methoxy-β-phenethyl)-3-thienylacetamide 
• 127035-90-9 2,6-Dimethyl-4-((E)-2-thiophen-3-yl-vinyl)-phenol 
• 214832-32-3 Pentafluorophenyl (thiophen-3-yl)ethanoate 
• 485370-79-4 Thiophen-3-yl-acetic acid 2-oxo-1,2-diphenyl-ethyl ester 
• 130553-74-1 N-Methyl-N-((1R,2S)-2-pyrrolidin-1-yl-cyclohexyl)-2-thiophen-3-yl-acetamide 
• 70474-53-2 N-(3',4'-dimethoxy-β-phenethyl)-3-thienylacetamide 
• 117498-49-4 <4-(carboxymethyl)-2-thienyl>(4-chloro-3-nitrophenyl)methanone 
• 116376-60-4 2,6-Di-tert-butyl-4-((E)-2-thiophen-3-yl-vinyl)-phenol 
• 13781-65-2 2-(thiophen-3-yl)acetyl chloride 
• 77014-10-9 2-(2,5-dibromo-thiophen-3-yl)acetic acid 
• 13781-67-4 3-(2-hydroxyethyl)thiophene 
• 37784-63-7 ethyl-3 thiophene acetate 
• 951235-93-1 C₁₄H₁₄O₃S 

Relevant articles and documents

Desulfonylative Electrocarboxylation with Carbon Dioxide

Electrocarboxylation of organic halides is one of the most investigated electrochemical approaches for converting thermodynamically inert carbon dioxide (CO2) into value-added carboxylic acids. By converting organic halides into their sulfone derivatives, we have developed a highly efficient electrochemical desulfonylative carboxylation protocol. Such a strategy takes advantage of CO2as the abundant C1 building block for the facile preparation of multifunctionalized carboxylic acids, including the nonsteroidal anti-inflammatory drug ibuprofen, under mild reaction conditions.

Synthesis of phenylacetic acids under rhodium-catalyzed carbonylation conditions

Benzyl halides are efficiently carbonylated to phenylacetic acids in the presence of a catalytic amount of the dimer of chloro(1,5-cyclooctadiene)rhodium(I) in formic acid. Under these reaction conditions, sensitive functionalities such as esters and nitriles are tolerated and the phenylacetic acids are obtained in good to high yields. (C) 2000 Elsevier Science Ltd.

Direct Carbonylation of Benzyl Alcohol and Its Analogs Catalyzed by Palladium and HI in Aqueous Systems and Mechanistic Studies

Carbonylation of benzyl alcohol, benzyl formate, dibenzyl ether, and benzyl phenylacetate catalyzed by palladium complexes and promoted by hydrogen iodide gives phenylacetic acid in moderate to excellent yields in aqueous systems. Application of the carbonylation process to other arylmethanol analogs provides convenient means to prepare 2-naphthaleneacetic acid, 3-isochromanone, 1,4-benzenediacetic acid, and o-hydroxybenzeneacetic acid. A mechanism for the catalytic reaction is proposed, which involves (1) formation of benzyl iodide by the reaction of benzyl alcohol with HI in situ, (2) oxidative addition of benzyl iodide to palladium(0) to form a benzylpalladium iodide species. (3) CO insertion into the Pd-benzyl bond to form a (phenylacetyl)palladium iodide species. (4) reductive elimination of phenylacetyl iodide, and (5) its hydrolysis into phenylacetic acid. Evidence supporting the mechanism was obtained by examining the properties of benzyl- and (phenylacetyl)palladium iodide and chloride complexes. Formation of benzyl(carbonyl)palladium species and migratory insertion of the benzyl group to CO was confirmed by means of NMR at low temperature under high pressure.