498-62-4

Basic information

• Product Name: 3-Thiophenecarboxaldehyde
• Synonyms: 3-THIOPHENE CARBOXALDEHYDE 98%;Thiophene-4-carbaldehyde;3-Thiophenecarboxaldehyde,98%;3-Thiophenecarboxald;3-Thiophenecarboxaldehyde, 98% 5ML;3- thiopheneforMaldehyde;Thiophene-3-carbaldehyde, 97+%;3-Thiophencarboxaldehyde
• CAS NO: 498-62-4
• Molecular Formula: C₅H₄OS
• Molecular Weight: 112.15
• EINECS: 207-865-5
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Aldehydes;Thiophenes & Benzothiophenes;Thiophene&Benzothiophene;Heterocyclic Compounds;Miscellaneous;Thiophens;Functional Materials;Reagents for Conducting Polymer Research;Thiophene Derivatives (for Conduting Polymer Research);Thiophen;Thiophenes & Benzothiophenes;Building Blocks;Heterocyclic Building Blocks;Thiophenes;Carbonyl Compounds;Heterocycles
• Mol File: 498-62-4.mol
• Article Data: 71

Chemical Properties

• Melting Point: -30 °C
• Boiling Point: 194-196 °C(lit.)
• Flash Point: 165 °F
• Appearance: Clear yellow to light brown/Liquid
• Density: 1.28 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.31 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.583(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Hexanes
• Water Solubility: Not miscible in water.
• Sensitive: Air Sensitive
• BRN: 105889
• CAS DataBase Reference: 3-Thiophenecarboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Thiophenecarboxaldehyde(498-62-4)
• EPA Substance Registry System: 3-Thiophenecarboxaldehyde(498-62-4)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-43-36/37/38
• Safety Statements: 37-24-36-26-36/37/39-20/21
• WGK Germany: 3
• TSCA: T
• HazardClass: AIR SENSITIVE
• Hazardous Substances Data: 498-62-4(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow to light brown liquid

Uses

3-Thiophenecarboxaldehyde is used in biological studies to determine the volatile compounds formed from the interaction between organoselenium and sulfur compounds.

Definition

ChEBI: An aldehyde that is thiophene substituted by a formyl group at position 3.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 16, p. 1361, 1973 DOI: 10.1021/jm00270a009Organic Syntheses, Coll. Vol. 4, p. 918, 1963

InChI:InChI=1/C5H4OS/c6-3-5-1-2-7-4-5/h1-4H

Synthetic route

3-hydroxymethyl-thiophene (71637-34-8) → 3-thiophene carboxaldehyde (498-62-4)

Conditions	Yield
With silica gel; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate In dichloromethane Ambient temperature;	96%
With oxygen In 1,3,5-trimethyl-benzene at 60℃; under 760.051 Torr; for 3h; Solvent; Reagent/catalyst;	95%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium nitrate; europium(III) nitrate hexahydrate; acetic acid In toluene at 40℃; for 9h;	95%

2,5-dihydro-3-thiophenecarboxaldehyde (113772-16-0) → 3-thiophene carboxaldehyde (498-62-4)

Conditions	Yield
With sulfuryl dichloride In dichloromethane at -36 - -30℃; for 0.5h;	92%
With sulfuryl dichloride In dichloromethane at -35℃;	58.9%

2-(thiophen-3-yl)-1,3-dithiane (1244041-07-3) → 3-thiophene carboxaldehyde (498-62-4)

Conditions	Yield
With eosin y In water; acetonitrile at 20℃; for 3h; Irradiation;	89%

3-Bromothiophene (872-31-1) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 3-thiophene carboxaldehyde (498-62-4)

Conditions	Yield
Stage #1: 3-Bromothiophene With n-butyllithium In diethyl ether; hexane at -78℃; for 1h; Stage #2: N,N-dimethyl-formamide In diethyl ether; hexane at -78 - 20℃; for 1.5h;	87.8%
Stage #1: 3-Bromothiophene With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In diethyl ether; hexane at 20℃; for 12h; Inert atmosphere;	70%

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%

C17H28OS2 → 3-thiophene carboxaldehyde (498-62-4)

Conditions	Yield
With triethylsilane In tetrahydrofuran for 1h; Reagent/catalyst; Fukuyama Reduction;	87%

3-thienyl iodide (10486-61-0) + carbon monoxide (201230-82-2) → 3-thiophene carboxaldehyde (498-62-4)

Conditions	Yield
With triethylsilane; palladium diacetate; sodium hydrogencarbonate; sodium carbonate at 20℃; under 760.051 Torr; for 48h;	84%
With rhodium(III) chloride trihydrate; hydrogen; triethylamine; triphenylphosphine In N,N-dimethyl acetamide at 90℃; under 7500.75 Torr; for 12h; Autoclave;	68%
With 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate; formic acid In N,N-dimethyl-formamide at 50℃; under 760 Torr; for 5h; Electrolysis;	82 % Chromat.

3-thienyl iodide (10486-61-0) + formic acid (64-18-6) → 3-thiophene carboxaldehyde (498-62-4)

Conditions	Yield
With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; tricyclohexylphosphine In N,N-dimethyl-formamide at 60℃; for 10h; Inert atmosphere; Sealed tube;	84%
Stage #1: 3-thienyl iodide; formic acid With palladium diacetate; acetic anhydride; tricyclohexylphosphine In N,N-dimethyl-formamide at 30℃; for 1h; Inert atmosphere; Green chemistry; Stage #2: With triethylamine In N,N-dimethyl-formamide at 80℃; for 6h; Inert atmosphere; Green chemistry;	65%

3-Bromothiophene (872-31-1) + carbon monoxide (201230-82-2) → 3-thiophene carboxaldehyde (498-62-4)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; hydrogen; palladium diacetate; propyl di-tert-butylphosphinite In toluene at 100℃; under 3750.38 Torr; for 20h; Inert atmosphere;	82%
With 4-methoxy-N'-tetramethylethylenediamine; hydrogen; catacxium A; palladium diacetate In toluene at 100℃; under 3750.3 Torr; for 16h;	82 % Chromat.
With N,N,N,N,-tetramethylethylenediamine; hydrogen; catacxium A; palladium diacetate In toluene at 100℃; under 3750.38 Torr; for 16h;	82 % Chromat.
With N,N,N,N,-tetramethylethylenediamine; C6H6*C48H78O2P2Pd; hydrogen In toluene at 20 - 100℃; under 3750.38 Torr; Inert atmosphere; Autoclave;	87 %Chromat.

3-thienyl iodide (10486-61-0) + carbon dioxide (124-38-9) → 3-thiophene carboxaldehyde (498-62-4)

Conditions	Yield
With dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; under 7500.75 Torr; for 20h; Autoclave; Green chemistry;	82%
With rhodium(III) iodide; hydrogen; acetic anhydride; triethylamine; triphenylphosphine In N,N-dimethyl acetamide at 100℃; for 24h; Autoclave;	60%

(CH3CNO)2(CH3CNOH)2Co(C5H5N)(OOCH2C4H3S) → 3-thiophene carboxaldehyde (498-62-4) + 3-hydroxymethyl-thiophene (71637-34-8)

Conditions	Yield
In methanol decomposition of the complex by refluxing in methanol under N2 for 6-8 h; evapn. of the solvent, extn. of the organic compounds with ether, gas chromatography;	A 19% B 81%

3-Bromothiophene (872-31-1) + carbon dioxide (124-38-9) → 3-thiophene carboxaldehyde (498-62-4)

Conditions	Yield
With dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 100℃; under 7500.75 Torr; for 20h; Autoclave; Green chemistry;	80%

3-Bromothiophene (872-31-1) + dicobalt octacarbonyl (15226-74-1, 61091-28-9, 61117-58-6) → 3-thiophene carboxaldehyde (498-62-4)

Conditions	Yield
With triethylsilane; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium acetate In acetonitrile at 60℃; for 16h; Schlenk technique; Inert atmosphere;	77%

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

Conditions	Yield
With palladium(II) acetylacetonate; hydrogen; 2,2-dimethylpropanoic anhydride; dicyclohexylphenylphosphine In tetrahydrofuran at 80℃; under 3750.38 Torr; for 20h; Inert atmosphere;	70%
With hydrogen; 2,2-dimethylpropanoic anhydride; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 80℃; under 22501.8 Torr; for 48h;	73 % Spectr.
Multi-step reaction with 2 steps 1: 88 percent / LiAlH4 / diethyl ether 2: 7.3 g / PCD / CH2Cl2 / 1.5 h View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride 2: pyridine 3: phosphorus (V)-chloride; benzene / anschliessend in Aether mit Zinn(II)-chlorid und Chlorwasserstoff behandeln und Erhitzen des vom Aether befreiten Reaktionsgemisches mit Wasser View Scheme

3-Bromothiophene (872-31-1) + 3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide (50978-45-5) → 3-thiophene carboxaldehyde (498-62-4)

Conditions	Yield
With triethylsilane; palladium diacetate; sodium carbonate; 1,4-di(diphenylphosphino)-butane In N,N-dimethyl-formamide at 80℃; Inert atmosphere; Sealed tube;	70%

3-styryl-thiophene (35022-11-8) → 3-thiophene carboxaldehyde (498-62-4) + naphtho[1,2-b]thiophene (234-41-3) + benzaldehyde (100-52-7) + [2,2']Bi[naphtho[1,2-b]thiophenyl] (78604-61-2)

Conditions	Yield
With oxygen In hexane Cyclization; oxidation; Irradiation;	A 8% B 69% C 8% D 15%
With oxygen In hexane at 25℃; Cyclization; oxidation; Irradiation;	A 8% B 69% C 8% D 15%

1,4-dithiane-2,5-diol (40018-26-6) + Malondialdehyde (542-78-9) → 3-thiophene carboxaldehyde (498-62-4)

Conditions	Yield
With diethylamine at 70℃; for 6h; Temperature; Reagent/catalyst;	65%

1-(thiophen-3-yl)-ethanone (1468-83-3) → 3-thiophene carboxaldehyde (498-62-4)

Conditions	Yield
With copper(l) iodide; oxygen In dimethyl sulfoxide at 120℃; for 19h; chemoselective reaction;	64%

3-thienyl iodide (10486-61-0) + carbon dioxide (124-38-9) → thiophene (188290-36-0) + 3-thiophene carboxaldehyde (498-62-4)

Conditions	Yield
With palladium on activated charcoal; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 80℃; for 20h; Autoclave;	A 27% B 64%

3-Bromothiophene (872-31-1) + formaldehyd (50-00-0) → 3-thiophene carboxaldehyde (498-62-4)

Conditions	Yield
With triethylsilane; dichloro bis(acetonitrile) palladium(II); sodium carbonate; 1,4-di(diphenylphosphino)-butane In N,N-dimethyl-formamide at 20 - 100℃; under 15001.5 Torr; for 20h; Inert atmosphere; Autoclave;	63%

C10H8OS2 → 3-thiophene carboxaldehyde (498-62-4) + 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
With sodium azide; copper(II) choride dihydrate; oxygen In N,N-dimethyl-formamide at 100℃; for 10h; Schlenk technique; Sealed tube;	A 47% B 53%

3-Bromomethylthiophene (34846-44-1) → 3-thiophene carboxaldehyde (498-62-4)

Conditions	Yield
	28%
With chloroform; hexamethylenetetramine Erhitzen des Reaktionsprodukts mit Wasserdampf oder mit wss. Aethanol;
Multi-step reaction with 2 steps 1: chloroform 2: water / Heating View Scheme
With 4-methylmorpholine N-oxide In ethyl acetate at 50℃; for 6h; Solvent;

1,4-dithiane-2,5-diol (40018-26-6) + 3-methoxyacrolein (4652-35-1) → 3-thiophene carboxaldehyde (498-62-4)

Conditions	Yield
1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 10℃; for 2h;	23%

3-formylthiophene diethyl acetal (3199-44-8) → 3-thiophene carboxaldehyde (498-62-4)

N-phenyl-3-thiophene-carboxamide (55797-29-0) → 3-thiophene carboxaldehyde (498-62-4)

Conditions	Yield
With phosphorus pentachloride; benzene anschliessend in Aether mit Zinn(II)-chlorid und Chlorwasserstoff behandeln und Erhitzen des vom Aether befreiten Reaktionsgemisches mit Wasser;

methyllithium (917-54-4) + thieno(3,2-d) isoselenazole (76835-01-3) → 3-thiophene carboxaldehyde (498-62-4) + 2-Methylselanyl-thiophene-3-carbonitrile + C10H4N2S2Se + 2-Methylselanyl-thiophene-3-carbaldehyde (76834-96-3)

Conditions	Yield
With water In tetrahydrofuran; diethyl ether at -80℃; for 5h; Product distribution;	A 16 % Chromat. B 18 % Chromat. C 26 % Chromat. D 100 % Chromat.

(3-thienyl)diazomethane (120361-26-4) → 3-thiophene carboxaldehyde (498-62-4)

Conditions	Yield
With oxygen In solid matrix at -233.2℃;

3-styryl-thiophene (35022-11-8) → 3-thiophene carboxaldehyde (498-62-4) + benzaldehyde (100-52-7)

Conditions	Yield
With oxygen; 9,10-Dicyanoanthracene In acetonitrile at 25℃; for 3h; Oxidation; Irradiation;	A 100 % Turnov. B 100 % Turnov.

3-thiophene carboxaldehyde (498-62-4) + diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) → (E)-3-thiophen-3-yl-acrylic acid ethyl ester (50266-60-9)

Conditions	Yield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Stage #2: 3-thiophene carboxaldehyde In tetrahydrofuran; mineral oil at 20℃; for 1h;	100%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: 3-thiophene carboxaldehyde In tetrahydrofuran; mineral oil at 0 - 20℃; for 3.25h;	100%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With potassium tert-butylate In tetrahydrofuran at 20℃; Stage #2: 3-thiophene carboxaldehyde In tetrahydrofuran at 90℃; for 0.5h;	90%

3-thiophene carboxaldehyde (498-62-4) + O,O-diethyl benzylphosphonate (1080-32-6) → (E)-3-styrylthiophene (78347-97-4)

Conditions	Yield
With sodium methylate In N,N-dimethyl-formamide at 0 - 20℃; for 1.75h;	100%

3-thiophene carboxaldehyde (498-62-4) + (R)-Phenylglycinol (56613-80-0) → (R)-2-Phenyl-2-{[1-thiophen-3-yl-meth-(E)-ylidene]-amino}-ethanol (139437-49-3)

Conditions	Yield
With magnesium sulfate In dichloromethane at 20℃; for 12h;	100%
In benzene Heating;	92%

3-thiophene carboxaldehyde (498-62-4) + benzylamine (100-46-9) → N-benzylthiophene-3-carbaldehyde imine

Conditions	Yield
With aluminum oxide for 12h;	100%

3-thiophene carboxaldehyde (498-62-4) + trimethyl phosphonoacetate (5927-18-4) → 3-Thiophen-3-yl-acrylic Acid Methyl Ester (75754-85-7)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0℃;	100%
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran for 1h; Stage #2: 3-thiophene carboxaldehyde In tetrahydrofuran at 20℃; for 18h;	94%
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 2h; Inert atmosphere; Stage #2: 3-thiophene carboxaldehyde In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere;	81%

3-thiophene carboxaldehyde (498-62-4) + (α-chloro-benzyl)-phosphonic acid diphenyl ester (58263-67-5) → 1-phenyl-2-(3-thienyl)ethyne (131423-29-5)

Conditions	Yield
Stage #1: 3-thiophene carboxaldehyde; (α-chloro-benzyl)-phosphonic acid diphenyl ester With potassium tert-butylate In tetrahydrofuran at 20℃; for 3h; Horner-Emmons reaction; Stage #2: With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Horner-Emmons reaction; Further stages.;	100%

3-thiophene carboxaldehyde (498-62-4) + diphenyl chloro(4-methoxycarbonylphenyl)methylphosphonate (189099-53-4) → 1-(4-methoxyphenyl)-2-(3-thienyl)ethyne

Conditions	Yield
Stage #1: 3-thiophene carboxaldehyde; diphenyl chloro(4-methoxycarbonylphenyl)methylphosphonate With potassium tert-butylate In tetrahydrofuran at 20℃; for 3h; Horner-Emmons reaction; Stage #2: With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Horner-Emmons reaction; Further stages.;	100%

3-thiophene carboxaldehyde (498-62-4) + diphenyl phosphonate (54335-03-4) → C12H7NO3S

Conditions	Yield
Stage #1: 3-thiophene carboxaldehyde; diphenyl phosphonate With potassium tert-butylate In tetrahydrofuran at 20℃; for 3h; Horner-Emmons reaction; Stage #2: With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Horner-Emmons reaction; Further stages.;	100%

3-thiophene carboxaldehyde (498-62-4) + Diphenyl 1-Chloro-1-(4-pyridyl)methanephosphonate (138517-18-7) → 4-(thien-3-ylethynyl)pyridine

Conditions	Yield
Stage #1: 3-thiophene carboxaldehyde; diphenyl 1-chloro-1-(4-pirydyl)methanephosphonate With potassium tert-butylate In tetrahydrofuran at 20℃; for 3h; Horner-Emmons reaction; Stage #2: With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Horner-Emmons reaction; Further stages.;	100%

3-thiophene carboxaldehyde (498-62-4) → 3-thiophenecarbaldoxime hydrochloride

Conditions	Yield
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water at 20℃; for 18h;	100%
With pyridine; hydroxylamine hydrochloride In ethanol at 20℃; for 2h;	90%
With pyridine; hydroxylamine hydrochloride In ethanol at 20℃; for 2h;	90%

3-thiophene carboxaldehyde (498-62-4) + malonic acid dimethyl ester (108-59-8) → dimethyl [(3-thienyl)methylene]malonate (1300690-47-4)

Conditions	Yield
With piperidine; benzoic acid for 12h; Heating / reflux;	100%
With piperidine; acetic acid In benzene for 4h; Reflux;	96%
With piperidine; acetic acid In benzene Dean-Stark; Reflux;

3-thiophene carboxaldehyde (498-62-4) + 4-phenyl-1-piperazine (92-54-6) → 1-phenyl-4-(thiophen-3-ylmethyl)piperazine (414887-78-8)

Conditions	Yield
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 18℃; for 2h; Solvent; Green chemistry;	100%

3-thiophene carboxaldehyde (498-62-4) + (E)-2-(buta-1,3-dien-1-yl)aniline (138386-62-6) → C15H13NS

Conditions	Yield
In ethanol at 80℃; Inert atmosphere;	100%

3-thiophene carboxaldehyde (498-62-4) → 3-thiophenecarboxaldehyde oxime (148134-23-0)

Conditions	Yield
With hydroxylamine hydrochloride In pyridine; water; ethyl acetate	99%
With hydroxylamine
With hydroxylamine hydrochloride; copper(II) sulfate at 90℃; for 2h;	85 % Spectr.
With hydroxylamine In methanol
With sodium chloride; hydroxylamine hydrochloride; sodium carbonate In ethanol; water

3-thiophene carboxaldehyde (498-62-4) + 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) → (E)-1-benzo[1,3]dioxol-5-yl-3-thiophen-3-ylpropenone

Conditions	Yield
Stage #1: 1-(benzo[d][1,3]dioxol-6-yl)ethanone With lithium hydroxide In ethanol at 20℃; for 0.166667h; Large scale; Stage #2: 3-thiophene carboxaldehyde In ethanol at 20℃; Large scale;	99%
With sodium hydroxide In ethanol; water

3-thiophene carboxaldehyde (498-62-4) + trimethylsilylacetylene (1066-54-2) → 1-(thiophen-3-yl)-3-(trimethylsilyl)prop-2-yn-1-ol (849769-14-8)

Conditions	Yield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: 3-thiophene carboxaldehyde In tetrahydrofuran at 0℃; for 1h;	99%
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran at 0℃; for 1h; Stage #2: 3-thiophene carboxaldehyde In tetrahydrofuran at 0℃; for 1h;	95%
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h;

3-thiophene carboxaldehyde (498-62-4) + 5-methyl-1H-indole (614-96-0) → 3,3'-bis-(5-methyl)-indolyl-3-thienylmethane

Conditions	Yield
With 1-hexyl-3-methylimidazolium hydrogen sulphate In ethanol at 20℃; for 1h;	99%

3-thiophene carboxaldehyde (498-62-4) + ethylene glycol (107-21-1) → 2-(thiophen-3-yl)-1,3-dioxolane (13250-82-3)

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 165℃; for 6h;	99%
With toluene-4-sulfonic acid In benzene Heating;	97%
toluene-4-sulfonic acid In toluene for 4h; Heating / reflux;	95.9%

3-thiophene carboxaldehyde (498-62-4) + 1-Heptylamine (111-68-2) → N-(3-thienylmethylene)-n-heptylamine

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 3h; Heating;	99%

3-thiophene carboxaldehyde (498-62-4) + methylmagnesium bromide (75-16-1) → 1-(thiophen-3-yl)ethan-1-ol (14861-60-0)

Conditions	Yield
In tetrahydrofuran at 0℃; for 2h;	99%

3-thiophene carboxaldehyde (498-62-4) + N-Phenylhydroxylamine (100-65-2) → (Z)-N-phenyl-1-(thiophen-3-yl)methanimine oxide

Conditions	Yield
In ethanol at 21℃; Inert atmosphere;	99%
In ethanol Heating; sonication;	79%

3-thiophene carboxaldehyde (498-62-4) + nitromethane (75-52-5) → (S)-(+)-2-nitro-1-(thiophen-3-yl)ethanol (1040923-87-2)

Conditions	Yield
With copper(II) acetate monohydrate; N-ethyl-N,N-diisopropylamine; N-<(1S,2R,4R)-1,7,7-trimethylbicyclo<2.2.1>hept-2-yl>-1-(2-pirydyl)methanamine In ethanol at -50℃; Henry reaction; optical yield given as %ee; enantioselective reaction;	99%

3-thiophene carboxaldehyde (498-62-4) + D,L-histidine (71-00-1) → C11H11N3O2S (1135901-64-2)

Conditions	Yield
With potassium carbonate In ethanol at 80℃; for 24h; Molecular sieve;	99%

3-thiophene carboxaldehyde (498-62-4) + 5-hydroxy-4,6-dimethyl-3-heptanone (71699-33-7) → thiophene-3-carboxylic acid (1SR,2SR,3SR)-3-hydroxy-1-isopropyl-2-methylpentyl ester

Conditions	Yield
With samarium diiodide; benzaldehyde In tetrahydrofuran at -15℃; for 1h; Evans-Tishchenko coupling reaction; Inert atmosphere; optical yield given as %de; diastereoselective reaction;	99%

3-thiophene carboxaldehyde (498-62-4) + 2-bromo-5-methoxy-benzaldehyde (7507-86-0) → 2-bromo-5-methoxybenzyl thiophene-3-carboxylate (1431656-04-0)

Conditions	Yield
With 4-tert-butylbenzyl mercaptan; dibutylmagnesium In tetrahydrofuran at 65℃; for 24h; Tishchenko-Claisen Dismutation; Inert atmosphere; chemoselective reaction;	99%

3-thiophene carboxaldehyde (498-62-4) + 2-bromoaniline (615-36-1) → C11H10BrNS

Conditions	Yield
In toluene at 130℃; Solvent; Temperature; Inert atmosphere; Molecular sieve;	99%

3-thiophene carboxaldehyde (498-62-4) + 1,1,3‐tribromo‐2,2‐dimethylcyclopropane (23534-97-6) → (3,3-dimethylcycloprop-1-en-1-yl)(thiophen-3-yl)methanol

Conditions	Yield
Stage #1: 1,1,3‐tribromo‐2,2‐dimethylcyclopropane With n-butyllithium In diethyl ether; hexane at -78 - -10℃; for 1h; Inert atmosphere; Stage #2: 3-thiophene carboxaldehyde In diethyl ether; hexane at -50 - -10℃; for 0.25h; Inert atmosphere;	99%

3-thiophene carboxaldehyde (498-62-4) + tryptamine (61-54-1) → 1-(thiophen-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride

Conditions	Yield
Stage #1: 3-thiophene carboxaldehyde; tryptamine With trifluoroacetic acid In 1,2-dichloro-ethane at 110℃; for 0.0333333h; Pictet-Spengler Synthesis; Sealed tube; Microwave irradiation; Stage #2: With hydrogenchloride In ethyl acetate at 20℃;	99%

3-thiophene carboxaldehyde (498-62-4) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → C11H17BO3S

Conditions	Yield
With FeBr2*2THF; C30H46N4Si2(2+) In acetonitrile at 20℃; for 12h; Glovebox; Inert atmosphere; Sealed tube;	99%

3-thiophene carboxaldehyde (498-62-4) + 2,2,4,4-tetramethyl-1,3-cyclobutanedione (933-52-8) → 6-(3’-thienyl)-3,3,5,5-tetramethyloxane-2,4-dione

Conditions	Yield
With potassium ethoxide In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	99%

Upstream product

• 71637-34-8 3-hydroxymethyl-thiophene 
• 190520-82-2 (E)-3-[2-(4-methylphenyl)ethenyl]thiophene 
• 35022-11-8 3-styryl-thiophene 
• 120361-26-4 (3-thienyl)diazomethane 
• 917-54-4 methyllithium 
• 76835-01-3 thieno(3,2-d) isoselenazole 
• 55797-29-0 N-phenyl-3-thiophene-carboxamide 
• 3199-44-8 3-formylthiophene diethyl acetal 
• 34846-44-1 3-Bromomethylthiophene 
• 872-31-1 3-Bromothiophene 
• 68-12-2 N,N-dimethyl-formamide 
• 15226-74-1 dicobalt octacarbonyl 
• 2746-23-8 3-(chloromethyl)thiophene 
• 1244041-07-3 2-(thiophen-3-yl)-1,3-dithiane 

Downstream Products

• 179018-86-1 [4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-thiophen-3-yl-methanol 
• 274917-29-2 [1-(2-Azido-phenyl)-ethyl]-[1-thiophen-3-yl-meth-(E)-ylidene]-amine 
• 34668-41-2 3-(PhCH₂NCH)C₄H₃S 
• 191922-43-7 3-SC₄H₃C(H)=NCy 
• 190520-82-2 (E)-3-[2-(4-methylphenyl)ethenyl]thiophene 
• 188481-44-9 (R)-(-)-2-hydroxy-2-(3-thienyl)acetonitrile 
• 102871-39-6 phenyl(thiophen-3-yl)methanol 
• 185243-98-5 N-(thiophen-3-yl(tosyl)methyl)formamide 

Relevant articles and documents

Photolysis of Diazo(3-thienyl)methane: A Simple Synthesis of a Methylenecyclopropene

-

-

-

Pyridinium Chlorochromate Supported on Montmorillonite–KSF as a Versatile Oxidant under Ball Milling Conditions

-

Dual-fixations of europium cations and TEMPO species on metal-organic frameworks for the aerobic oxidation of alcohols

The efficient and selective aerobic oxidation of alcohols has been investigated with judicious combinations of europium-incorporated and/or TEMPO ((2,2,6,6-tetramethylpiperidin-1-yl)oxyl)-functionalized zirconium-based porous metal-organic frameworks (MOFs). Although MOFs are well-known catalytic platforms for the aerobic oxidation with radical-functionalities and metal nanoparticles, these systematic approaches involving metal cations and/or radical species introduce numerous interesting aspects for cooperation between metals and TEMPO for the aerobic oxidation of alcohols. The role of TEMPO as the oxidant in the heterogeneous catalytic aerobic oxidation of alcohols was revealed through a series of comparisons between metal-anchored, TEMPO-anchored, and metal and TEMPO-anchored MOF catalysis. The fine tunability of the MOF allowed the homogeneously and doubly functionalized catalysts to undergo organic reactions in the heterogeneous media. In addition, the well-defined and carefully designed heterogeneous molecular catalysts displayed reusability along with better catalytic performance than the homogeneous systems using identical coordinating ligands. The role of metal-cation fixation should be carefully revised to control their coordination and maximize their catalytic activity. Lastly, the metal cation-fixed MOF displayed better substrate tolerance and reaction efficiencies than the TEMPO-anchored MOF or mixture MOF systems.