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CAS No.: | 498-62-4 |
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Name: | 3-Thiophenecarboxaldehyde |
Article Data: | 81 |
Molecular Structure: | |
Formula: | C5H4OS |
Molecular Weight: | 112.152 |
Synonyms: | 3-Formylthiophene;3-Thienaldehyde;3-Thienylcarboxaldehyde;3-Thiophenealdehyde;NSC 172858;Thiophen-3-aldehyde; |
EINECS: | 207-865-5 |
Density: | 1.238 g/cm3 |
Melting Point: | -30 °C |
Boiling Point: | 190.6 °C at 760 mmHg |
Flash Point: | 73.9 °C |
Solubility: | Not miscible in water. |
Appearance: | clear yellow to light brown liquid |
Hazard Symbols: | Xn, Xi |
Risk Codes: | 22-43-36/37/38 |
Safety: | 37-24-36-26 |
PSA: | 45.31000 |
LogP: | 1.56060 |
3-hydroxymethyl-thiophene
3-thiophene carboxaldehyde
Conditions | Yield |
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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
3-thiophene carboxaldehyde
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
3-thiophene carboxaldehyde
Conditions | Yield |
---|---|
With eosin y In water; acetonitrile at 20℃; for 3h; Irradiation; | 89% |
Conditions | Yield |
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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
A
3-thiophene carboxaldehyde
B
3-Thiophene carboxylic acid
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-thiophene carboxaldehyde
Conditions | Yield |
---|---|
With triethylsilane In tetrahydrofuran for 1h; Reagent/catalyst; Fukuyama Reduction; | 87% |
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. |
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% |
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. |
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% |
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