88-13-1

Basic information

• Product Name: 3-Thiophenezoic acid
• Synonyms: 3-Carboxythiophene;Thiophene-3-carboxylic acid ,99%;3-Thenoylic acid;3-Thiophenecarboxylic acid,99%;3-Thiophenecarboxylic acid, 99% 1GR;3-Thiophenecarboxylic Acid 3-Thiophenic Acid;3-Carboxythiophene, 3-Thenoic acid;3 - thiophene forMic acid
• CAS NO: 88-13-1
• Molecular Formula: C₅H₄O₂S
• Molecular Weight: 128.15
• EINECS: 201-802-5
• Product Categories: Thiophens;Functional Materials;Reagents for Conducting Polymer Research;Thiophene Derivatives (for Conduting Polymer Research);Thiophen;Building Blocks;Heterocyclic Building Blocks;Thiophenes;Thiophene&Benzothiophene;Organic acids;Heterocyclic Compounds
• Mol File: 88-13-1.mol
• Article Data: 52

Chemical Properties

• Melting Point: 136-141 °C(lit.)
• Boiling Point: 260°C (estimate)
• Flash Point: 117.765 °C
• Appearance: White to slightly yellow/Crystalline Powder
• Density: 1.305 (estimate)
• Vapor Pressure: 0.00323mmHg at 25°C
• Refractive Index: 1.5160 (estimate)
• Storage Temp.: Refrigerated.
• Solubility: water: soluble0.2g/10 mL, clear to almost clear, colorless to sl
• PKA: 4.1(at 25℃)
• Water Solubility: 4.3 g/L (25 ºC)
• Merck: 14,9279
• BRN: 1994
• CAS DataBase Reference: 3-Thiophenezoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Thiophenezoic acid(88-13-1)
• EPA Substance Registry System: 3-Thiophenezoic acid(88-13-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26-36
• WGK Germany: 3
• RTECS: XM8330300
• HazardClass: IRRITANT
• Hazardous Substances Data: 88-13-1(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

3-Thiophenecarboxylic Acid was used as a lading compound for the development of a clinic useful D-amino acid inhibitor and have the potential to sever as active site proves to elucidate the structure-function relationships of D-amino acids.

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 1555, 1948 DOI: 10.1021/ja01184a078Organic Syntheses, Coll. Vol. 4, p. 919, 1963

General Description

Mechanism of photopolymerization of 3-thiophenecarboxylic acid catalyzed by potassium dichromate has been reported.

InChI:InChI=1/C5H4O2S/c6-5(7)4-1-2-8-3-4/h1-3H,(H,6,7)

Synthetic route

3-Bromothiophene (872-31-1) + carbon dioxide (124-38-9) → 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
Stage #1: carbon dioxide With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate In 1,4-dioxane at 65℃; for 0.333333h; Schlenk technique; Stage #2: 3-Bromothiophene With palladium diacetate; triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane; toluene at 100℃; for 7h; Schlenk technique; Sealed tube;	94%
Stage #1: carbon dioxide With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate In 1,4-dioxane at 60℃; for 0.416667h; Schlenk technique; Stage #2: 3-Bromothiophene With palladium diacetate; triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane; toluene at 100℃; for 7h; Schlenk technique;	94%
With manganese; 2.9-dimethyl-1,10-phenanthroline; lithium acetate; cobalt(II) bromide In N,N-dimethyl acetamide at 20℃; under 760.051 Torr; for 12h; Inert atmosphere; Schlenk technique;	65%

3-thienyl iodide (10486-61-0) + formic acid (64-18-6) → 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere; Sealed tube;	90%
With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 100℃; for 20h; Inert atmosphere; Sealed tube;	46%

2-(thiophen-3-yl)-5,5-dimethyl-1,3,2-dioxaborinane (905966-46-3) + carbon dioxide (124-38-9) → 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
Stage #1: 5,5-dimethyl-2-(thiophen-3-yl)-1,3,2-dioxaborinane; carbon dioxide With [Ni(N,N'-bis[2,6-bis(diphenylmethyl)-4-methylphenyl]imidazole-2-ylidene)(allyl)Cl]; potassium tert-butylate In toluene at 100℃; under 760.051 Torr; for 15h; Schlenk technique; Inert atmosphere; Stage #2: With hydrogenchloride In water; ethyl acetate; toluene at 20℃;	88%
Stage #1: 5,5-dimethyl-2-(thiophen-3-yl)-1,3,2-dioxaborinane; carbon dioxide With potassium tert-butylate; silver(I) acetate; triphenylphosphine In 1,4-dioxane at 100℃; under 15201 Torr; for 8h; Inert atmosphere; Autoclave; Stage #2: With hydrogenchloride In tetrahydrofuran; water Inert atmosphere;	83%
With 1,3-bis-(diphenylphosphino)propane; cesium fluoride; [Rh(OH)(cod)]2 In 1,4-dioxane at 60℃;	64%

3-hydroxymethyl-thiophene (71637-34-8) → 3-thiophene carboxaldehyde (498-62-4) + 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
With sodium hypochlorite; C8H18NPol; sodium hydrogencarbonate In water; toluene at 15 - 20℃; for 4.5h; Product distribution / selectivity;	A 87.5% B 0.1%
With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; oxygen In 1,2-dichloro-ethane at 25℃; for 48h; Schlenk technique;	A 18 %Spectr. B 65%
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate In water; toluene at 15 - 20℃; for 4.5h; Product distribution / selectivity;	A 52.3% B 2.3%

3-ethynylthiophene (67237-53-0) → 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
With oxone; sodium hydrogencarbonate In water; acetonitrile at 20℃; for 8h;	86%
With carbon tetrabromide; water; oxygen In ethyl acetate for 20h; Irradiation;	16%

3-thienyl iodide (10486-61-0) + carbon dioxide (124-38-9) → 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
With 3,4-benzo-1,1,2,2-tetraethyl-1,2-disilacyclobut-3-ene; cesium fluoride In N,N-dimethyl-formamide at 0 - 20℃; under 760.051 Torr; for 2h;	85%

3-thienyl iodide (10486-61-0) + carbon monoxide (201230-82-2) → 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
With water; palladium diacetate; potassium carbonate at 20℃; under 760.051 Torr; for 12h;	84%

3-hydroxymethyl-thiophene (71637-34-8) → 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
With hydrogen bromide; oxygen In acetonitrile for 10h; Irradiation;	83%
With carbon tetrabromide; oxygen; triphenylphosphine In acetonitrile for 10h; fluorescent irradiation;	80%
With dichloro(1,5-cyclooctadiene)ruthenium(II); C30H30N3P2(1+)*Cl(1-); potassium hydroxide In toluene at 120℃; for 24h; Inert atmosphere; Schlenk technique;	76%

3-thiophene carboxaldehyde (498-62-4) → 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
With water; chromium(VI) oxide In diethyl ether	80%
With chromic acid In diethyl ether at 0℃; for 3h;	80%
With sodium hydroxide; silver(l) oxide

3-Bromothiophene (872-31-1) + methanol (67-56-1) + carbon monoxide (201230-82-2) → methyl thiophene-3-carboxylate (22913-26-4) + 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
With CoCRACO; sodium tert-pentoxide; sodium hydride In tetrahydrofuran for 14h; Irradiation;	A 80% B 12.5%
With tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 14h; Irradiation;	A 80% B 12.5%

3-Bromothiophene (872-31-1) + carbon monoxide (201230-82-2) → methyl thiophene-3-carboxylate (22913-26-4) + 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
With methanol; tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 14h; Irradiation;	A 80% B 12.5%

3-chlorothiophene (17249-80-8) + methanol (67-56-1) + carbon monoxide (201230-82-2) → methyl thiophene-3-carboxylate (22913-26-4) + 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
With tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 17h; Irradiation;	A 77.5% B 8.5%

3-chlorothiophene (17249-80-8) + carbon monoxide (201230-82-2) → methyl thiophene-3-carboxylate (22913-26-4) + 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
With methanol; tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 17h; Irradiation;	A 77.5% B 8.5%

3-Methylthiophene (616-44-4) → 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
at 30℃; for 16h; Pseudomonas putida ATCC 33015;	70%
With sodium dichromate In water at 250℃; for 16h;	60%
With oxygen; cobalt(II) acetate; sodium bromide In acetic acid at 100℃; for 1.5h; Kinetics; Rate constant;

1-(thiophen-3-yl)butane-1,3-dione → 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
With 2-chloroanthracene-9,10-dione; oxygen; caesium carbonate In acetone for 48h; Irradiation;	70%
With iodine; oxygen In ethyl acetate for 10h; Mercury lamp irradiation;	57%

C21H22O2SSi → 3-Thiophene carboxylic acid (88-13-1) + 2-(tert-Butyl-diphenyl-silanyl)-thiophene-3-carboxylic acid

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -78℃; for 0.25h;	A n/a B 64%

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

Conditions	Yield
With iodine; dimethyl sulfoxide at 120℃; for 26h; Sealed tube; Green chemistry;	62%

C14H24O2SSi → 3-Thiophene carboxylic acid (88-13-1) + 2-Triisopropylsilanyl-thiophene-3-carboxylic acid

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -78℃; for 0.25h;	A n/a B 57%

3-chlorothiophene (17249-80-8) + carbon dioxide (124-38-9) → 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
With manganese; 2,9-dibutyl-4,7-dimethyl-1,10-phenanthroline; tetraethylammonium iodide; lithium acetate; cobalt(II) bromide In N,N-dimethyl acetamide at 100℃; under 760.051 Torr; for 12h; Inert atmosphere; Schlenk technique;	51%

C11H18O2SSi → 3-Thiophene carboxylic acid (88-13-1) + 2-(tert-Butyl-dimethyl-silanyl)-thiophene-3-carboxylic acid

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -78℃; for 0.25h;	A n/a B 47%

thiophene (188290-36-0) + carbon monoxide (201230-82-2) → β-thiophen carboxylic anhydride (13191-43-0) + 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
With palladium diacetate; ethylene dibromide at 100℃; under 11400 Torr; for 20h;	A 35% B 42%

3-thienyl iodide (10486-61-0) + malononitrile (109-77-3) → 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
Stage #1: 3-thienyl iodide; malononitrile With copper(l) iodide; caesium carbonate; L-proline In dimethyl sulfoxide at 130℃; for 24h; Ullmann type reaction; Inert atmosphere; Stage #2: In dimethyl sulfoxide at 140℃; for 12h; Stage #3: With hydrogenchloride In water pH=2 - 3;	37%

Thien-3-ylboronic acid (6165-69-1) + ethyl acetoacetate (141-97-9) → 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
With copper(l) iodide; potassium carbonate In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere;	27%

3-Bromothiophene (872-31-1) + n-butyllithium (109-72-8, 29786-93-4) + diethyl ether (60-29-7) → 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
at -70℃; anschliessend mit festem Kohlendioxid;

3-Bromothiophene (872-31-1) + ethylmagnesium bromide (925-90-6) + benzene (71-43-2) → 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
anschliessenden Behandeln mit Kohlendioxid;

3-Bromothiophene (872-31-1) → 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
With ethyl bromide; diethyl ether; magnesium Behandeln des Reaktionsgemisches mit festem Kohlendioxid;
With n-butyllithium; diethyl ether at -70℃; Behandeln des Reaktionsgemisches mit festem Kohlendioxid;

3-thienyl iodide (10486-61-0) + potassium cyanide (151-50-8) → 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
With ethanol; copper(l) cyanide at 180℃;

3-thienyl iodide (10486-61-0) → 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
With ethyl bromide; diethyl ether; magnesium anschliessend Behandeln mit Kohlendioxid;

3-thiophenecarbonitrile (1641-09-4) → 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
With hydrogenchloride

diazomethane (186581-53-3, 908094-01-9) + 3-Thiophene carboxylic acid (88-13-1) → methyl thiophene-3-carboxylate (22913-26-4)

Conditions	Yield
In diethyl ether	100%

3-Thiophene carboxylic acid (88-13-1) + acetaldehyde (75-07-0) → 2-(1-hydroxy-ethyl)-thiophene-3-carboxylic acid (329351-95-3)

Conditions	Yield
Stage #1: 3-Thiophene carboxylic acid With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; Stage #2: acetaldehyde In tetrahydrofuran; pentane at -78 - 20℃;	100%
Stage #1: 3-Thiophene carboxylic acid With lithium hexamethyldisilazane In tetrahydrofuran at -80 - -50℃; for 1h; Stage #2: acetaldehyde In tetrahydrofuran at -80 - -20℃; for 0.5h; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 20℃;

3-Thiophene carboxylic acid (88-13-1) + 2-(piperidin-1-ylmethyl)-1H-benzo[d]imidazol-5-amine → N-(2-(piperidin-1-ylmethyl)-1H-benzo[d]imidazol-5-yl)thiophene-3-carboxamide

Conditions	Yield
With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane for 16h;	100%

3-Thiophene carboxylic acid (88-13-1) → β-thiophen carboxylic anhydride (13191-43-0)

Conditions	Yield
Stage #1: 3-Thiophene carboxylic acid With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0℃; Stage #2: With bis(trichloromethyl) carbonate In tetrahydrofuran at 0 - 20℃;	99%
With acetic anhydride; toluene
With 2,4,6-trimethyl-pyridine; bis(trichloromethyl) carbonate In tetrahydrofuran for 0.0166667h;
Multi-step reaction with 2 steps 1.1: potassium hydroxide / water / 0.5 h / 20 °C 2.1: trichloroisocyanuric acid; triphenylphosphine / dichloromethane / 0 - 20 °C 2.2: 2 h / 20 °C View Scheme

dichloromethane (75-09-2) + 3-Thiophene carboxylic acid (88-13-1) → C11H8O4S2

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 130℃; for 5h;	99%

3-Thiophene carboxylic acid (88-13-1) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2-formylthiophene-3-carboxylic acid (19991-69-6)

Conditions	Yield
Stage #1: 3-Thiophene carboxylic acid With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78℃; for 0.166667h; Stage #2: With n-butyllithium In tetrahydrofuran for 1h; Stage #3: N,N-dimethyl-formamide In tetrahydrofuran for 0.5h;	98.3%
Stage #1: 3-Thiophene carboxylic acid With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78℃; for 0.166667h; Inert atmosphere; Stage #2: With n-butyllithium In tetrahydrofuran for 1h; Stage #3: N,N-dimethyl-formamide In tetrahydrofuran for 0.5h;	98.3%

3-Thiophene carboxylic acid (88-13-1) → 2-bromothiophene-4-carboxylic acid (100523-84-0)

Conditions	Yield
With bromine; acetic acid at 20℃;	98%
With bromine In acetic acid	74%
With bromine In acetic acid	70%

3-Thiophene carboxylic acid (88-13-1) + 7,13-O,O-diacetyl-2-O-debenzoylbaccatin III (329318-51-6) → 7,13-O,O-diacetyl-2-O-debenzoyl-2-O-(3-thiophenecarbonyl)baccatin III (1215640-85-9)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran; toluene at 80℃; for 36h; Inert atmosphere;	98%

3-Thiophene carboxylic acid (88-13-1) + (S)-allyl 2-(allyloxy)-4-(2-(allyloxy)-4-(4-(2-(4-aminobenzamido)-3-cyanopropanamido)benzamido)-3-methoxybenzamido)-3-methoxybenzoate → C48H44N6O11S

Conditions	Yield
Stage #1: 3-Thiophene carboxylic acid With 2,4,6-trimethyl-pyridine; bis(trichloromethyl) carbonate In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Stage #2: (S)-allyl 2-(allyloxy)-4-(2-(allyloxy)-4-(4-(2-(4-aminobenzamido)-3-cyanopropanamido)benzamido)-3-methoxybenzamido)-3-methoxybenzoate With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 12h;	98%

3-Thiophene carboxylic acid (88-13-1) → 3-thiophene carboxylic acid chloride (41507-35-1)

Conditions	Yield
With oxalyl dichloride In dichloromethane for 1.91667h; Inert atmosphere; Reflux;	97%
With oxalyl dichloride In dichloromethane at 0 - 20℃;	91%
With oxalyl dichloride In dichloromethane at 0℃; for 12h;	78%

3-Thiophene carboxylic acid (88-13-1) + L-proline methyl ester monohydrochloride (2133-40-6) → methyl (2S)-N-(3-thiophenecarbonyl)pyrrolidin-2-carboxylate (849795-61-5)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃;	97%

potassium thiophene-3-carboxylate + 3-Thiophene carboxylic acid (88-13-1) → β-thiophen carboxylic anhydride (13191-43-0)

Conditions	Yield
Stage #1: 3-Thiophene carboxylic acid With trichloroisocyanuric acid; triphenylphosphine In dichloromethane at 0 - 20℃; Stage #2: potassium thiophene-3-carboxylate In dichloromethane at 20℃; for 2h;	97%

benzoxazole (273-53-0) + 3-Thiophene carboxylic acid (88-13-1) → 2-(thiophen-3-yl)benzo[d]oxazole (638213-72-6)

Conditions	Yield
With dmap; copper (II)-fluoride; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Schlenk technique; Inert atmosphere; chemoselective reaction;	97%

3-Thiophene carboxylic acid (88-13-1) → 2,5-dibromothiophene-3-carboxylic acid (7311-70-8)

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide Inert atmosphere; Darkness;	95%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 50℃; for 28h; Darkness; Inert atmosphere;	92%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 50℃; for 18h; Darkness;	88%

3-Thiophene carboxylic acid (88-13-1) + 1,2-diamino-benzene (95-54-5) → 2-(thiophen-3-yl)-1H-benzo[d]imidazole (3878-21-5)

Conditions	Yield
With PPA at 180℃; for 1.5h;	95%

3-Thiophene carboxylic acid (88-13-1) + dimethyl dicarbonate (4525-33-1) → methyl thiophene-3-carboxylate (22913-26-4)

Conditions	Yield
magnesium(II) perchlorate In nitromethane at 40℃; for 16h;	95%

1,4-dioxane (123-91-1) + 3-Thiophene carboxylic acid (88-13-1) → 1,4-dioxan-2-yl thiophene-3-carboxylate (1597710-78-5)

Conditions	Yield
With iron(III)-acetylacetonate; di-tert-butyl peroxide at 120℃; for 24h; Schlenk technique;	95%

1-phenyl-1-butyne (622-76-4) + 3-Thiophene carboxylic acid (88-13-1) → 7-ethyl-6-phenyl-4H-thieno[3,2-c]pyran-4-one + 6-ethyl-7-phenyl-4H-thieno[3,2-c]pyran-4-one

Conditions	Yield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; oxygen; sodium acetate In methanol at 45℃; under 760.051 Torr; for 18h; Schlenk technique; regioselective reaction;	A 95% B 2%

3-Thiophene carboxylic acid (88-13-1) + aminoguanidine bicarbonate (2582-30-1) → amino(hydrazinyl)methaniminium thiophene-3-carboxylate

Conditions	Yield
In methanol at 50℃;	94%

3-Thiophene carboxylic acid (88-13-1) + 5,6-dimethoxy-2-(N-propylamino)indan (162751-96-4) → thiophene-3-carboxylic acid (5,6-dimethoxy-indan-2-yl)-propyl-amide (745060-12-2)

Conditions	Yield
With diethyl cyanophosphonate; triethylamine In dichloromethane at 20℃; for 24h;	93%

di-tert-butyl dicarbonate (24424-99-5) + 3-Thiophene carboxylic acid (88-13-1) → tert-butyl thiophene-3-carboxylate (125294-45-3)

Conditions	Yield
magnesium(II) perchlorate In nitromethane at 40℃; for 16h;	93%

3-Thiophene carboxylic acid (88-13-1) + dibenzyl dicarbonate (31139-36-3) → benzyl thiophene-3-carboxylate (14597-48-9)

Conditions	Yield
magnesium(II) perchlorate In nitromethane at 40℃; for 16h;	93%

3-Thiophene carboxylic acid (88-13-1) + 4-cyclohexyl-thiosemicarbazide (21198-18-5) → cyclohexyl-(5-thiophen-3-yl-[1,3,4]thiadiazol-2-yl)-amine

Conditions	Yield
With trichlorophosphate In 1,4-dioxane at 60 - 95℃; for 5h;	93%

3-Thiophene carboxylic acid (88-13-1) + thiosemicarbazide (79-19-6) → cyclohexyl-(5-thiophen-3-yl-[1,3,4]thiadiazol-2-yl)-amine

Conditions	Yield
With sodium hydrogencarbonate; trichlorophosphate In 1,4-dioxane	93%

3-Thiophene carboxylic acid (88-13-1) + diphenyl acetylene (501-65-5) → 6,7-diphenyl-4H-thieno[3,2-c]pyran-4-one (1147304-41-3)

Conditions	Yield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; oxygen; sodium acetate In methanol at 45℃; under 760.051 Torr; for 18h; Schlenk technique; regioselective reaction;	93%
With dichloro[1,3-di(ethoxycarbonyl)-2,4,5-trimethylcyclopentadienyl]rhodium(III) dimer; copper(II) acetate monohydrate; silver(I) triflimide In dichloromethane at 20℃; for 24h; Sealed tube;	74%
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In N,N-dimethyl-formamide at 120℃; for 2h;	60%
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate In water at 120℃; for 0.5h; Microwave irradiation; Green chemistry;	45%

3-Thiophene carboxylic acid (88-13-1) + 4-iodobenzonitrile (3058-39-7) → 4-cyanophenyl thiophene-3-carboxylate

Conditions	Yield
With potassium phosphate; 1-(2,2-diphenyl-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ij]quinolin-1(2H)-yl)-3-phenylpropan-1-one; 4,4'-di-tert-butyl-2,2'-bipyridine; nickel dibromide In dimethyl sulfoxide at 25℃; for 22h; Irradiation;	93%

3-Thiophene carboxylic acid (88-13-1) + 2-iodophenylamine (615-43-0) → N-(2-iodophenyl)thiophene-3-carboxamide (136341-16-7)

Conditions	Yield
Stage #1: 3-Thiophene carboxylic acid With thionyl chloride In toluene at 70℃; for 2.5h; Stage #2: 2-iodophenylamine With TEA In dichloromethane at 20℃; for 5h;	92%

1-(3-dimethylaminopropyl)-3-ethylcabodiimide hydrochloride + 3-Thiophene carboxylic acid (88-13-1) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → thiophene-3-(N-methoxy-N-methyl)carboxamide (357405-56-2)

Conditions	Yield
With 4-methyl-morpholine; dmap In dichloromethane	92%

3-Thiophene carboxylic acid (88-13-1) + 4-[(2S',6S')-6'-(4-((6-aminohexyl)oxy)butyl)tetrahydropyran-2-yl]-1-[(2S'',6S'')-6''-(4-hydroxybutyltetrahydropyran-2-yl)methyl]-1H-1,2,3-triazole → N-(6-(4-((2S,6S)-6-((4-((2S,6S)-6-(4-(benzyloxy)butyl)tetrahydro-2H-pyran-2-yl)-1H-1,2,3-triazol-1-yl)methyl)tetrahydro-2H-pyran-2-yl)butoxy)hexyl)thiophene-3-carboxamide

Conditions	Yield
Stage #1: 3-Thiophene carboxylic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.166667h; Stage #2: 4-[(2S',6S')-6'-(4-((6-aminohexyl)oxy)butyl)tetrahydropyran-2-yl]-1-[(2S'',6S'')-6''-(4-hydroxybutyltetrahydropyran-2-yl)methyl]-1H-1,2,3-triazole In dichloromethane at 20℃;	92%

Upstream product

• 872-31-1 3-Bromothiophene 
• 109-72-8 n-butyllithium 
• 60-29-7 diethyl ether 
• 925-90-6 ethylmagnesium bromide 
• 71-43-2 benzene 
• 10486-61-0 3-thienyl iodide 
• 151-50-8 potassium cyanide 
• 498-62-4 3-thiophene carboxaldehyde 
• 1641-09-4 3-thiophenecarbonitrile 
• 91-22-5 quinoline 
• 859492-72-1 2-(methyl-phenyl-carbamoyl)-thiophene-3-carboxylic acid 
• 497-19-8 sodium carbonate 
• 36157-41-2 2,5-dichlorothiophene-3-carboxylic acid 
• 188290-36-0 thiophene 

Downstream Products

• 41507-35-1 3-thiophene carboxylic acid chloride 
• 18133-20-5 thiolane-3-carboxylic acid 
• 36157-42-3 2-chlorothiophene-4-carboxylic acid 
• 100523-84-0 2-bromothiophene-4-carboxylic acid 
• 36157-41-2 2,5-dichlorothiophene-3-carboxylic acid 
• 7311-70-8 2,5-dibromothiophene-3-carboxylic acid 
• 16694-22-7 2,4,5-tribromothiophene-3-carboxylic acid 
• 40357-96-8 5-nitro-thiophene-3-carboxylic acid 
• 56421-77-3 2-(thiophen-3-yl)benzo[d]thiazole 
• 498-62-4 3-thiophene carboxaldehyde 
• 26453-81-6 di(thiophen-3-yl)methanone 
• 913982-20-4 Thiophene-3-carboxylic acid {(S)-1-[1-((S)-1-carbamoyl-pentyl)-1H-[1,2,3]triazol-4-yl]-1-cyclohexyl-ethyl}-amide 
• 913982-22-6 Thiophene-3-carboxylic acid [(S)-1-[1-((S)-1-carbamoyl-pentyl)-1H-[1,2,3]triazol-4-yl]-1-(4-methyl-cyclohexyl)-ethyl]-amide 
• 55797-29-0 N-phenyl-3-thiophene-carboxamide 

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