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3-Cyanomethylthiophene Basic information Product Name: 3-Cyanomethylthiophene Synonyms: Thiophen-3-yl-acetonitrile;3-thiopheneacetonitrile:3-cyan
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3-Thiopheneacetonitrile cas 13781-53-8Appearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum Application:intermediate Transportation:by air, by sea, by express
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Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; bis(η3-allyl-μ-chloropalladium(II)) In 1,3,5-trimethyl-benzene at 20 - 140℃; for 5.16667h; Inert atmosphere; Sealed tube; chemoselective reaction; | 78% |
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; sodium carbonate In 1,4-dioxane; water at 100℃; for 12h; Inert atmosphere; Sealed tube; | 53% |
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; sodium carbonate In 1,4-dioxane; water at 60℃; for 12h; Inert atmosphere; Sealed tube; |
Conditions | Yield |
---|---|
tetrabutylammomium bromide In dichloromethane; water Heating / reflux; | 44% |
With ethanol |
Conditions | Yield |
---|---|
With N-benzyl-N,N,N-triethylammonium chloride In water | 28% |
Conditions | Yield |
---|---|
With ethanol |
3-thiophene carboxaldehyde
[(p-methylphenyl)sulfonylmethyl]isonitrile
(thiophen-3-yl)acetonitrile
Conditions | Yield |
---|---|
With potassium tert-butylate 1.) THF, -20 deg C, 30 min, 2.) THF, -20 deg C, 30 min; Yield given. Multistep reaction; |
Methyl 2-cyano-2-(3-thienyl)acetate
(thiophen-3-yl)acetonitrile
Conditions | Yield |
---|---|
With water; triethylamine Product distribution; |
3-Methylthiophene
(thiophen-3-yl)acetonitrile
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 1 h / Reflux 2: tetrabutyl ammonium fluoride / acetonitrile; tetrahydrofuran / 0 - 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; dibenzoyl peroxide 2: N-benzyl-N,N,N-triethylammonium chloride / water View Scheme |
3-Bromomethylthiophene
trimethylsilyl cyanide
(thiophen-3-yl)acetonitrile
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran; acetonitrile at 0 - 20℃; Inert atmosphere; | 4.06 g |
(thiophen-3-yl)acetonitrile
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
With 2,4-dichlorophenoxyacetic acid dimethylamine In toluene Heating; | 100% |
(thiophen-3-yl)acetonitrile
methanol
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether at 0 - 5℃; | 99% |
(thiophen-3-yl)acetonitrile
2-methylphenyl aldehyde
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol | 98% |
(thiophen-3-yl)acetonitrile
2-(3-thienyl)ethylamine
Conditions | Yield |
---|---|
With indium(III) chloride; sodium tetrahydroborate In tetrahydrofuran at 25℃; for 4h; Inert atmosphere; | 97% |
With diisobutylaluminum borohydride In tetrahydrofuran at 25℃; for 1h; Inert atmosphere; | 71% |
With indium(III) chloride; sodium tetrahydroborate In tetrahydrofuran at 25℃; for 16h; Inert atmosphere; | 67% |
(thiophen-3-yl)acetonitrile
2-amino-benzenethiol
2-((thiophen-3-yl)methyl)benzo[d]thiazole
Conditions | Yield |
---|---|
With copper diacetate; triethylamine In ethanol at 70℃; for 6h; | 97% |
thiophene-2-carbaldehyde
(thiophen-3-yl)acetonitrile
(Z)-3-Thiophen-2-yl-2-thiophen-3-yl-acrylonitrile
Conditions | Yield |
---|---|
With sodium methylate In methanol at 30℃; Kinetics; Thermodynamic data; ΔE*, Σ*, A; | 95% |
(thiophen-3-yl)acetonitrile
benzaldehyde
(E)-3-phenyl-2-(3-thienyl)acrylonitrile
Conditions | Yield |
---|---|
With sodium methylate In methanol at 30℃; Kinetics; Thermodynamic data; ΔE*, Σ*, A; | 95% |
With sodium ethanolate In ethanol | 94% |
With potassium tert-butylate In ethanol Heating; | 60% |
With potassium tert-butylate In ethanol at 20℃; Knoevenagel condensation; | 60% |
With sodium ethanolate In ethanol at 4℃; for 8h; | 51% |
(thiophen-3-yl)acetonitrile
4-Octyne
(Z)-2-propyl-3-(3-thienylmethyl)-2-hexenenitrile
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel(0); dimethylaluminum chloride; 2-dicyclohexylphosphino-2',4',6'-trimethylbiphenyl In hexane; toluene at 80℃; for 2h; Inert atmosphere; stereoselective reaction; | 95% |
With bis(1,5-cyclooctadiene)nickel (0); dimethylaluminum chloride; 2-dicyclohexylphosphino-2',4',6'-trimethylbiphenyl In hexane; tetradecane; toluene at 80℃; for 2h; Inert atmosphere; regioselective reaction; | 95% |
(thiophen-3-yl)acetonitrile
2-(thiophen-3-yl) ethanamine hydrochloride
Conditions | Yield |
---|---|
Stage #1: (thiophen-3-yl)acetonitrile With borane-dimethyl sulfide complex In tetrahydrofuran for 16h; Reflux; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 0.333333h; | 94% |
Stage #1: (thiophen-3-yl)acetonitrile With dimethylsulfide borane complex In tetrahydrofuran for 16h; Heating / reflux; Stage #2: With methanol In tetrahydrofuran | 94% |
Stage #1: (thiophen-3-yl)acetonitrile With dimethylsulfide borane complex In tetrahydrofuran for 16h; Heating / reflux; Stage #2: With hydrogenchloride; methanol at 20℃; for 0.333333h; | 94% |
Stage #1: (thiophen-3-yl)acetonitrile With dimethylsulfide borane complex In tetrahydrofuran for 12h; Reflux; Stage #2: With hydrogenchloride In tetrahydrofuran for 0.5h; | 78.5% |
Stage #1: (thiophen-3-yl)acetonitrile With borane-THF In tetrahydrofuran at 20℃; Inert atmosphere; Reflux; Stage #2: With methanol In tetrahydrofuran Stage #3: With hydrogenchloride In 1,4-dioxane; methanol |
(thiophen-3-yl)acetonitrile
Conditions | Yield |
---|---|
With sodium azide; triethylamine hydrochloride In toluene at 110℃; for 16h; Inert atmosphere; | 93% |
With aluminium trichloride; sodium azide In tetrahydrofuran for 48h; Heating; | 61% |
(thiophen-3-yl)acetonitrile
4,4-bis(methylthio)but-3-en-2-one
Conditions | Yield |
---|---|
Stage #1: (thiophen-3-yl)acetonitrile With sodium hydride In N,N-dimethyl-formamide; benzene for 0.25h; Metallation; Stage #2: 4,4-bis(methylthio)but-3-en-2-one In N,N-dimethyl-formamide at 20℃; Substitution; | 93% |
(thiophen-3-yl)acetonitrile
ethanol
Conditions | Yield |
---|---|
With hydrogenchloride at 0℃; Pinner reaction; | 93% |
(thiophen-3-yl)acetonitrile
bis(acetonitrile)diiodotricarbonyltungsten(II)
triphenylphosphine
WI2(CO)3(thiophene-3-acetonitrile)(PPh3)
Conditions | Yield |
---|---|
In dichloromethane N2-atmosphere; stirring W-complex with equimolar amt. of PPh3 for 3 min,filtration into equimolar amt. of ligand soln., stirring for 30 min; solvent removal (vac.); elem. anal.; | 93% |
(thiophen-3-yl)acetonitrile
Conditions | Yield |
---|---|
With N-iodo-succinimide; toluene-4-sulfonic acid In ethanol at 50℃; for 0.166667h; Green chemistry; regioselective reaction; | 93% |
(thiophen-3-yl)acetonitrile
Glyoxilic acid
(2Z)-3-cyano-3-(3-thienyl)acrylic acid
Conditions | Yield |
---|---|
With potassium carbonate In methanol for 3h; Knoevenagel Condensation; Reflux; | 90% |
With potassium carbonate In methanol for 3h; Heating / reflux; | 90% |
(thiophen-3-yl)acetonitrile
methyl iodide
rac-2-(thiophen-2-yl)propanenitrile
Conditions | Yield |
---|---|
Stage #1: (thiophen-3-yl)acetonitrile With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; | 90% |
(thiophen-3-yl)acetonitrile
cyclopropyl(4-fluorophenyl)methanone
9a-(4-fluorophenyl)-7,8,9,9a-tetrahydrothieno[3,2-g]indolizin-5(4H)-one
Conditions | Yield |
---|---|
With tributylphosphine; boron trifluoride diethyl etherate; copper(I) bromide In nitromethane at 90℃; for 18h; Ritter Amidation; | 90% |
(thiophen-3-yl)acetonitrile
bis(acetonitrile)diiodotricarbonyltungsten(II)
WI2(CO)3(thiophene-3-acetonitrile)2
Conditions | Yield |
---|---|
In dichloromethane N2-atmosphere; stirring W-complex with 2 equiv. of ligand (warm water bath, 90 min, then room temp., 1 h); filtration, solvent removal (vac.); elem. anal.; | 89% |
(thiophen-3-yl)acetonitrile
2-(thiophene-3-yl) acetamide
Conditions | Yield |
---|---|
With water at 130℃; for 1h; Microwave irradiation; | 88% |
With copper(l) iodide; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene In nitromethane; water at 20 - 100℃; for 3h; | 75% |
(thiophen-3-yl)acetonitrile
methyl (4-methoxyphenyl)carbodithioate
Conditions | Yield |
---|---|
Stage #1: (thiophen-3-yl)acetonitrile With potassium tert-butylate In 1,4-dioxane at 0℃; for 0.166667h; Stage #2: methyl (4-methoxyphenyl)carbodithioate In 1,4-dioxane at 0 - 20℃; for 1h; Stage #3: With iodine In 1,4-dioxane at 90℃; | 87% |
(thiophen-3-yl)acetonitrile
α,α'-dichloroazo compound
Conditions | Yield |
---|---|
With antimonypentachloride In dichloromethane at -60 - 23℃; for 2.16667h; | 86% |
(thiophen-3-yl)acetonitrile
formic acid ethyl ester
Conditions | Yield |
---|---|
With sodium methylate In methanol for 2h; Heating; | 85% |
(thiophen-3-yl)acetonitrile
allyl bromide
2-allyl-2-(thiophen-3-yl)pent-4-enenitrile
Conditions | Yield |
---|---|
Stage #1: (thiophen-3-yl)acetonitrile With sodium hydride In dimethyl sulfoxide at 20℃; for 0.5h; Inert atmosphere; Stage #2: allyl bromide In dimethyl sulfoxide at 20℃; for 2h; Inert atmosphere; | 85% |
(thiophen-3-yl)acetonitrile
4-chlorophenyl cyclopropyl ketone
9a-(4-chlorophenyl)-7,8,9,9a-tetrahydrothieno[3,2-g]indolizin-5(4H)-one
Conditions | Yield |
---|---|
With tributylphosphine; boron trifluoride diethyl etherate; copper(I) bromide In nitromethane at 90℃; for 18h; Ritter Amidation; | 84% |
(thiophen-3-yl)acetonitrile
cyclopropyl phenyl ketone
9a-phenyl-7,8,9,9a-tetrahydrothieno[3,2-g]indolizin-5(4H)-one
Conditions | Yield |
---|---|
With tributylphosphine; boron trifluoride diethyl etherate; copper(I) bromide In nitromethane at 90℃; for 18h; Ritter Amidation; | 84% |
(thiophen-3-yl)acetonitrile
N-Hydroxy-2-thiophen-3-yl-acetamidine
Conditions | Yield |
---|---|
With potassium carbonate; ammonium chloride In methanol at 60℃; for 12h; | 83% |
(thiophen-3-yl)acetonitrile
bis-(1-chloro-1-methyl-ethyl)-diazene
Conditions | Yield |
---|---|
With antimonypentachloride In dichloromethane at -60 - 23℃; for 2.16667h; | 83% |
(thiophen-3-yl)acetonitrile
methyl 4-bromocrotonate
Conditions | Yield |
---|---|
Stage #1: (thiophen-3-yl)acetonitrile With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: methyl 5-(dimethylamino)thiophene-2-carbodithioate In tetrahydrofuran at 0℃; for 0.5h; Stage #3: methyl 4-bromocrotonate In tetrahydrofuran at 0 - 20℃; for 8.5h; | 82% |
(thiophen-3-yl)acetonitrile
hexachlorobenzene
Conditions | Yield |
---|---|
With n-butyllithium In diethyl ether 1.) -70 deg C, 2 h, 2.) -70 deg C to r.t.; r.t., overnight; | 80% |
(thiophen-3-yl)acetonitrile
methyl fluorobenzenedithiocarboxylate
Conditions | Yield |
---|---|
Stage #1: (thiophen-3-yl)acetonitrile With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.166667h; Stage #2: methyl fluorobenzenedithiocarboxylate In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; Stage #3: With tetrabutylammomium bromide; copper diacetate; palladium diacetate In N,N-dimethyl-formamide; mineral oil at 90℃; | 80% |
Stage #1: (thiophen-3-yl)acetonitrile With potassium tert-butylate In 1,4-dioxane at 0℃; for 0.166667h; Stage #2: methyl fluorobenzenedithiocarboxylate In 1,4-dioxane at 0 - 20℃; for 1h; Stage #3: With iodine In 1,4-dioxane at 90℃; | 77% |
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