2687-91-4

Basic information

• Product Name: N-Ethyl-2-pyrrolidone
• Synonyms: 1-ethyl-2-pyrrolidinon;1-ethyl-pyrrolidin-2-one;2-Pyrrolidinone, 1-ethyl-;Agsol Ex 2;ethyl-2-pyrrolidone;N-Ethyl-2-pyrrolidinone;N-Ethylpyrrolidinone;N-Ethylpyrrolidone
• CAS NO: 2687-91-4
• Molecular Formula: C₆H₁₁NO
• Molecular Weight: 113.16
• EINECS: 220-250-6
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Pyrrolidines;Pyrrolidones
• Mol File: 2687-91-4.mol
• Article Data: 30

Chemical Properties

• Melting Point: 87.5-88.5 °C
• Boiling Point: 97 °C20 mm Hg(lit.)
• Flash Point: 169 °F
• Appearance: Clear/Liquid
• Density: 0.992 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.276mmHg at 25°C
• Refractive Index: n20/D 1.465(lit.)
• Storage Temp.: -70°C
• PKA: -0.41±0.20(Predicted)
• Explosive Limit: 1.3-7.7%(V)
• Water Solubility: 1000g/L at 23℃
• BRN: 107971
• CAS DataBase Reference: N-Ethyl-2-pyrrolidone(CAS DataBase Reference)
• NIST Chemistry Reference: N-Ethyl-2-pyrrolidone(2687-91-4)
• EPA Substance Registry System: N-Ethyl-2-pyrrolidone(2687-91-4)

Safety Data

• Hazard Codes: Xn,T
• Statements: 22-36-62-41-61
• Safety Statements: 26-36-45-36/37/39-53
• WGK Germany: 1
• RTECS: UY5769250
• TSCA: Yes
• Hazardous Substances Data: 2687-91-4(Hazardous Substances Data)

Usage

Chemical Properties

clear liquid

Uses

1-Ethyl-2-pyrrolidone was used to modify coir fiber (from Cocos nucifera) by photocuring.

General Description

1-Ethyl-2-pyrrolidone is a transdermal absorption-enhancing compound and mechanism of its effect on multilammellar liposome of stratum corneum lipid has been studied.

Flammability and Explosibility

Nonflammable

Safety Profile

Moderately toxic by ingestion. An eye irritant. Combustible. When heated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C6H11NO/c1-2-7-5-3-4-6(7)8/h2-5H2,1H3

Synthetic route

1-ethenyl-2-pyrrolidinone (88-12-0) → 1-ethyl-2-pyrrolidinone (2687-91-4)

Conditions	Yield
With C7H14N3(1+)*Cl(1-); sodium triethylborohydride; cobalt(II) chloride In tetrahydrofuran at 25℃; under 7500.75 Torr; for 16h;	99%
With ammonium formate; palladium on activated charcoal In methanol for 0.5h; Heating;	94%
With oxygen; hydrazine hydrate; 7-(trifluoromethyl)-1,10-ethyleneisoalloxazinium chloride In water at 100℃; under 760.051 Torr; for 18h;	88%

4-butanolide (96-48-0) + ethylamine (75-04-7) → 1-ethyl-2-pyrrolidinone (2687-91-4)

Conditions	Yield
In water; ethylene glycol at 290℃; under 38787.1 Torr; Kinetics; Temperature; Concentration; Flow reactor;	93.9%
at 300℃;
at 215℃;

1-ethenyl-2-pyrrolidinone (88-12-0) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 1-ethyl-2-pyrrolidinone (2687-91-4) + 1-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl)pyrrolidin-2-one (1190639-19-0)

Conditions	Yield
With Rh(acac)(dppb) In tetrahydrofuran for 18h; Inert atmosphere; regioselective reaction;	A n/a B 83%

N,N-diethyl-2-diazoacetamide (6112-00-1) → 1-ethyl-2-pyrrolidinone (2687-91-4)

Conditions	Yield
dirhodium tetraacetate In dichloromethane at 40℃; for 5h;	77%

2-pyrrolidinon (616-45-5) + ethyl bromide (74-96-4) → 1-ethyl-2-pyrrolidinone (2687-91-4)

Conditions	Yield
Stage #1: 2-pyrrolidinon; ethyl bromide With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Stage #2: at 0℃;	75%

N-trimethylsilyl-pyrrolidin-2-one (14468-90-7) + Ethyl benzenesulfonate (515-46-8) → 1-ethyl-2-pyrrolidinone (2687-91-4) + trimethylsilyl benzenesulfonate (17882-06-3)

Conditions	Yield
Heating;	A 59% B 72%

4-butanolide (96-48-0) + ethanolamine (141-43-5) → 1-ethyl-2-pyrrolidinone (2687-91-4)

Conditions	Yield
ZSM-5	69%

4-butanolide (96-48-0) + triethylamine (121-44-8) → 1-ethyl-2-pyrrolidinone (2687-91-4) + ethanol (64-17-5)

Conditions	Yield
ZSM-5	A 68% B 13%

2-pyrrolidinon (616-45-5) + ethene (74-85-1) → 1-ethyl-2-pyrrolidinone (2687-91-4)

Conditions	Yield
With silver tetrafluoroborate; dibromo[1,3-dihydro-1-(2-pyridinyl)-3-(2,4,6-trimethylphenyl)-2H-imidazol-2-ylidene]platinum(II) In nitrobenzene-d5 at 20 - 150℃; under 4125.41 Torr; for 26h; Inert atmosphere;	59%

N,N-diethyl-2-diazoacetamide (6112-00-1) → 1-ethyl-2-pyrrolidinone (2687-91-4) + 1-ethyl-4-methyl-2-azetidinone (31366-13-9) + C12H22N2O2 (111328-65-5)

Conditions	Yield
With Cu(1+)*HB(C3N2Br3)3(1-)=(HB(C3N2Br3)3)Cu In dichloromethane at 20℃; Inert atmosphere; chemoselective reaction;	A 51% B 20% C 17%
With copper(I) hydrotris(3,5-dimethylpyrazol-1-yl)borate In dichloromethane at 20℃; Inert atmosphere; chemoselective reaction;

2-pyrrolidinon (616-45-5) + ethyl iodide (75-03-6) → 1-ethyl-2-pyrrolidinone (2687-91-4)

Conditions	Yield
With sodium hydride Heating;	42%

N,N-diethyl-2-diazoacetamide (6112-00-1) → N1,N1,N4,N4-tetraethylmaleamide + 1-ethyl-2-pyrrolidinone (2687-91-4) + N1,N1,N4,N4-tetraethylfumaramide (111328-65-5, 138895-86-0, 37511-04-9)

Conditions	Yield
Ru2(CO)4[(PrO)4-5,17-Br2-11,23-(CO2-)2-calix[4]arene] In dichloromethane at 40℃; for 24h;	A 17% B 23% C 14%

4-butanolide (96-48-0) + water (7732-18-5) + triethylamine (121-44-8) → 1-ethyl-2-pyrrolidinone (2687-91-4) + ethanol (64-17-5)

Conditions	Yield
Conversion of starting material;	A n/a B 13%

N-ethylsuccinimide (2314-78-5) → 1-ethyl-2-pyrrolidinone (2687-91-4)

Conditions	Yield
With sulfuric acid; water Bei der elektrolytischen Reduktion an einer Blei-Kathode.;
With 5% active carbon-supported ruthenium; hydrogen In water at 150℃; under 112511 Torr; for 6h; Green chemistry;

4-(N,N-diethylamino)butanoic acid (63867-13-0) → 1-ethyl-2-pyrrolidinone (2687-91-4)

Conditions	Yield
With phosphorus trichloride Erhitzen des Reaktionsprodukts auf 155-160grad.;

3-hydroxy-4-nitro-butyric acid ethyl ester (854852-25-8) → 1-ethyl-2-pyrrolidinone (2687-91-4)

Conditions	Yield
With 1,4-dioxane; ethanol; copper oxide-chromium oxide at 260℃; under 191232 Torr; Hydrogenation;

methanol (67-56-1) + N,N-diethyl-2-diazoacetamide (6112-00-1) → 1-ethyl-2-pyrrolidinone (2687-91-4) + 1-ethyl-4-methyl-2-azetidinone (31366-13-9) + N,N-diethylglycine methyl ester (30280-35-4) + 2-methoxy-N,N-diethyl-acetamide (70814-00-5)

Conditions	Yield
at 0℃; for 0h; Product distribution; Irradiation; variuos temp.;	A 16.8 % Chromat. B 37.5 % Chromat. C 11.9 % Chromat. D n/a

N-acetyl-α-pyrrolidone → 1-ethyl-2-pyrrolidinone (2687-91-4)

Conditions	Yield
With sulfuric acid at 45℃; elektrolytische Reduktion;

N-ethylsuccinimide (2314-78-5) + sulfuric acid (7664-93-9) + water (7732-18-5) → 1-ethylpyrrolidine (7335-06-0) + 1-ethyl-2-pyrrolidinone (2687-91-4)

Conditions	Yield
at 28℃; elektrochemischen Reduktion an einer Blei-Kathode;

1,4-dioxane (123-91-1) + ethanol (64-17-5) + 3-hydroxy-4-nitro-butyric acid ethyl ester (854852-25-8) + copper oxide-chromium oxide → 1-ethylpyrrolidine (7335-06-0) + 1-ethyl-2-pyrrolidinone (2687-91-4)

Conditions	Yield
at 260℃; under 191232 Torr; Hydrogenation;

4-(ethylamino)butyric acid (76572-84-4) + water (7732-18-5) → 1-ethyl-2-pyrrolidinone (2687-91-4)

Conditions	Yield
at 100℃; vom pH 1.2 bis pH 12.7;

4-(ethylamino)butyric acid (76572-84-4) + butan-1-ol (71-36-3) → 1-ethyl-2-pyrrolidinone (2687-91-4) + water (7732-18-5)

Conditions	Yield
at 100℃;

2-pyrrolidinon (616-45-5) + C2H5X → 1-ethyl-2-pyrrolidinone (2687-91-4)

Conditions	Yield
With sodium hydride at 60 - 70℃;

1-(2-hydroxyethyl)-2-pyrrolidinone (3445-11-2) → 2-pyrrolidinon (616-45-5) + 1-ethyl-2-pyrrolidinone (2687-91-4) + 1-ethenyl-2-pyrrolidinone (88-12-0)

Conditions	Yield
0.37 - 1.6 % cesium on silica In water at 350 - 375℃; for 3 - 95h; Product distribution / selectivity;
0.37 - 1.6 % cesium on silica at 350 - 375℃; for 3 - 95h; Product distribution / selectivity;

1-ethenyl-2-pyrrolidinone (88-12-0) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 1-ethyl-2-pyrrolidinone (2687-91-4) + ((CH3)4C2O2)BCHCHNC4H6O (1190639-18-9) + 1-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl)pyrrolidin-2-one (1190639-19-0)

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In benzene-d6 for 18h; Inert atmosphere;

2-pyrrolidinon (616-45-5) + ethanol (64-17-5) → 1-ethyl-2-pyrrolidinone (2687-91-4)

Conditions	Yield
With ammonium bromide at 250℃; for 5h; Autoclave;

deuteromethanol (1455-13-6) + N,N-diethyl-2-diazoacetamide (6112-00-1) → 1-ethyl-2-pyrrolidinone (2687-91-4) + 1-ethyl-4-methyl-2-azetidinone (31366-13-9) + C7H14(2)HNO2 (1167575-44-1)

Conditions	Yield
Irradiation;

N,N-diethyl-2-diazoacetamide (6112-00-1) → 1-ethyl-2-pyrrolidinone (2687-91-4) + 1-ethyl-4-methyl-2-azetidinone (31366-13-9)

Conditions	Yield
In chloroform Irradiation;

1-ethyl-2-pyrrolidinone (2687-91-4) + trifluoroacetic anhydride (407-25-0) → (Z)-3-(1-chloro-2,2,2-trifluoroethylidene)-1-ethylpyrrolidin-2-one

Conditions	Yield
With aluminum (III) chloride In N,N-dimethyl-formamide at 60℃; for 24h;	95%

1-ethyl-2-pyrrolidinone (2687-91-4) → N-ethylsuccinimide (2314-78-5)

Conditions	Yield
With ruthenium(IV) oxide; sodium periodate In ethyl acetate for 15h; Ambient temperature;	93%

1-ethyl-2-pyrrolidinone (2687-91-4) + dimethyl sulfate (77-78-1) → C7H14NO(1+)*CH3O4S(1-)

Conditions	Yield
In neat (no solvent) at 20℃; for 12h; Inert atmosphere;	92%

1-ethyl-2-pyrrolidinone (2687-91-4) + Tosyl isocyanate (4083-64-1) → (E)-N-(1-ethylpyrrolidin-2-ylidene)-4-methylbenzenesulfonamide (131657-47-1)

Conditions	Yield
In tetrahydrofuran at 20℃; for 18h;	91%

styrene (292638-84-7) + 1-ethyl-2-pyrrolidinone (2687-91-4) → N-ethyl-3-phenethylpyrrolidin-2-one + N-ethyl-3,3-diphenethylpyrrolidin-2-one

Conditions	Yield
With potassium tert-butylate at 80℃; for 2h; Sealed tube;	A 86% B 5%

1-ethyl-2-pyrrolidinone (2687-91-4) → 1-ethylpyrrolidine hydrochloride

Conditions	Yield
Stage #1: 1-ethyl-2-pyrrolidinone With bis(cyclopentadienyl)dihydrozirconium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane at 20℃; under 760.051 Torr; for 12h; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether Inert atmosphere;	86%

1-ethyl-2-pyrrolidinone (2687-91-4) → 1-Ethylpyrrolidine-2-thione

Conditions	Yield
With Lawessons reagent In tert-butyl methyl ether at 20℃; for 16h; Inert atmosphere;	85%
With Lawessons reagent In benzene for 4h; Heating;	83%
Multi-step reaction with 2 steps 1: POCl3 / CH2Cl2 / 0.5 h / -78 °C 2: hexamethyldisilathiane / CH2Cl2 / 6 h / Ambient temperature View Scheme

1-ethyl-2-pyrrolidinone (2687-91-4) + 3-pyridinecarboxylic acid ethyl ester (614-18-6) → 1-ethyl-3-nicotinoyl-2-pyrrolidinone

Conditions	Yield
With sodium hydride In toluene for 48h; Heating;	85%

1-ethyl-2-pyrrolidinone (2687-91-4) + 2-Adamantanone (700-58-3) → 2-(1-ethyl-2-oxopyrrolidin-3-yl)tricyclo[3.3.1.13,7]decan-2-ol (913335-86-1)

Conditions	Yield
Stage #1: 1-ethyl-2-pyrrolidinone With lithium diisopropyl amide In tetrahydrofuran; diethyl ether; hexane at -80℃; for 0.333333h; Stage #2: 2-Adamantanone In tetrahydrofuran; diethyl ether; hexane at -80 - 20℃; Further stages.;	84%
Stage #1: 1-ethyl-2-pyrrolidinone With lithium diisopropyl amide at -70℃; Stage #2: 2-Adamantanone In tetrahydrofuran at -80℃;

1-ethyl-2-pyrrolidinone (2687-91-4) + (E)-methyl 2-(2-methoxy-3-oxoisoindolin-1-ylidene)acetate (1333433-21-8) → (E)-methyl 2-(1-ethyl-5-oxopyrrolidin-2-yl)-2-(3-oxoisoindolin-1-ylidene)acetate

Conditions	Yield
With air at 100℃; for 3h; Green chemistry; regioselective reaction;	82%

1-ethyl-2-pyrrolidinone (2687-91-4) + mono-6-deoxy-6-(p-tolylsulphonyl)-β-cyclodextrin (67217-55-4) → 6I-O-(N-ethyl-4-aminobutanoyl)cyclomaltoheptaose p-toluenesulfonate

Conditions	Yield
at 90℃;	80%

1-ethyl-2-pyrrolidinone (2687-91-4) + (E)-methyl 2-(2-methoxy-4-methyl-3-oxoisoindolin-1-ylidene)acetate (1352122-79-2) → (E)-methyl 2-(1-ethyl-5-oxopyrrolidin-2-yl)-2-(4-methyl-3-oxoisoindolin-1-ylidene)acetate

Conditions	Yield
With air at 100℃; for 12h; Green chemistry; regioselective reaction;	79%

1-ethyl-2-pyrrolidinone (2687-91-4) + (4-bromophenyl)magnesium bromide (18620-02-5) → 5-(4-bromophenyl)-1-ethyl-2,3-dihydropyrrole (1109230-92-3)

Conditions	Yield
Stage #1: 1-ethyl-2-pyrrolidinone; (4-bromophenyl)magnesium bromide In diethyl ether at 20℃; Cooling with ice; Inert atmosphere; Stage #2: With hydrogenchloride; water In diethyl ether pH=3 - 4; Cooling with ice; Stage #3: With sodium hydroxide In water	78%

1-ethyl-2-pyrrolidinone (2687-91-4) + phenylmagnesium bromide (100-58-3) → 1-ethyl-5-phenyl-2,3-dihydropyrrole (1109230-81-0)

Conditions	Yield
Stage #1: 1-ethyl-2-pyrrolidinone; phenylmagnesium bromide In diethyl ether at 20℃; Cooling with ice; Inert atmosphere; Stage #2: With hydrogenchloride; water In diethyl ether pH=3 - 4; Cooling with ice; Stage #3: With sodium hydroxide In water	78%

1-ethyl-2-pyrrolidinone (2687-91-4) → 4-(ethylamino)butan-1-ol (39216-86-9)

Conditions	Yield
With ethanol; sodium In hexane at 0℃; for 0.333333h; Inert atmosphere; chemoselective reaction;	78%
With ethanol; sodium In hexane; paraffin oil at 0℃; for 0.0833333h; Inert atmosphere;	22%

1-ethyl-2-pyrrolidinone (2687-91-4) + (4-chlorphenyl)magnesium bromide (873-77-8) → 5-(4-chlorophenyl)-1-ethyl-2,3-dihydropyrrole (1109230-91-2)

Conditions	Yield
Stage #1: 1-ethyl-2-pyrrolidinone; (4-chlorphenyl)magnesium bromide In diethyl ether at 20℃; Cooling with ice; Inert atmosphere; Stage #2: With hydrogenchloride; water In diethyl ether pH=3 - 4; Cooling with ice; Stage #3: With sodium hydroxide In water	75%

1-ethyl-2-pyrrolidinone (2687-91-4) + benzonitrile (100-47-0) → C20H19N3

Conditions	Yield
With potassium tert-butylate at 110℃; for 16h;	74%

1-ethyl-2-pyrrolidinone (2687-91-4) → N-ethylsuccinimide (2314-78-5) + N-acetylpyrrolidinone (932-17-2)

Conditions	Yield
With pyridine; N-hydroxyphthalimide; sodium perchlorate In acetonitrile Product distribution; Mechanism; controlled potential electrolysis, electrodes: glassy-carbon vs. SCE;	A 73% B 11%
With pyridine; N-hydroxyphthalimide; sodium perchlorate In acetonitrile controlled potential electrolysis, electrodes: glassy-carbon vs. SCE;	A 73% B 11%

1-ethyl-2-pyrrolidinone (2687-91-4) + toluene-4-sulfonamide (70-55-3) → (E)-N-(1-ethylpyrrolidin-2-ylidene)-4-methylbenzenesulfonamide (131657-47-1)

Conditions	Yield
With diazoacetic acid ethyl ester; zinc trifluoromethanesulfonate In cyclohexane for 12h; Reflux; stereoselective reaction;	73%

1-ethyl-2-pyrrolidinone (2687-91-4) + (E)-methyl 2-(2,5-dimethoxy-3-oxoisoindolin-1-ylidene)acetate (1352122-82-7) → (E)-methyl 2-(1-ethyl-5-oxopyrrolidin-2-yl)-2-(5-methoxy-3-oxoisoindolin-1-ylidene)acetate

Conditions	Yield
With air at 100℃; for 12h; Green chemistry; regioselective reaction;	72%

1-ethyl-2-pyrrolidinone (2687-91-4) + 4-methoxyphenyl magnesium bromide (13139-86-1) → 1-ethyl-5-(4-methoxyphenyl)-2,3-dihydropyrrole (1109230-89-8)

Conditions	Yield
Stage #1: 1-ethyl-2-pyrrolidinone; 4-methoxyphenyl magnesium bromide In diethyl ether at 20℃; Cooling with ice; Inert atmosphere; Stage #2: With hydrogenchloride; water In diethyl ether pH=3 - 4; Cooling with ice; Stage #3: With sodium hydroxide In water	71%

1-ethyl-2-pyrrolidinone (2687-91-4) + 4-flourophenylmagnesium bromide (352-13-6) → 1-ethyl-5-(4-fluorophenyl)-2,3-dihydropyrrole (1109230-90-1)

Conditions	Yield
Stage #1: 1-ethyl-2-pyrrolidinone; 4-flourophenylmagnesium bromide In diethyl ether at 20℃; Cooling with ice; Inert atmosphere; Stage #2: With hydrogenchloride; water pH=3 - 4; Cooling with ice; Stage #3: With sodium hydroxide In water	70%

1-ethyl-2-pyrrolidinone (2687-91-4) + phenanthridine (229-87-8) → 1-ethyl-5-(phenanthridin-6′-yl)pyrrolidin-2-one

Conditions	Yield
With trifluoroacetic acid; dibenzoyl peroxide In water at 35 - 40℃; for 24h; Inert atmosphere; Irradiation; regioselective reaction;	70%

Upstream product

• 96-48-0 4-butanolide 
• 75-04-7 ethylamine 
• 854852-25-8 3-hydroxy-4-nitro-butyric acid ethyl ester 
• 76572-84-4 4-(ethylamino)butyric acid 
• 14468-90-7 N-trimethylsilyl-pyrrolidin-2-one 
• 515-46-8 Ethyl benzenesulfonate 
• 6112-00-1 N,N-diethyl-2-diazoacetamide 
• 88-12-0 1-ethenyl-2-pyrrolidinone 
• 1333-74-0 hydrogen 
• 616-45-5 2-pyrrolidinon 
• 74-96-4 ethyl bromide 
• 74-85-1 ethene 
• 1455-13-6 deuteromethanol 
• 64-17-5 ethanol 

Downstream Products

• 100632-81-3 ibutilide 
• 130350-55-9 N-[{4-(N-ethyl-N-heptylamino)butanoyl}phenyl]methanesulfonamide 
• 1374247-24-1 2-cyclohexyl-1-ethylpyrrolidine 
• 7335-06-0 1-ethylpyrrolidine 
• 1467101-15-0 (Z)-1-ethyl-5-styrylpyrrolidin-2-one 
• 1467101-25-2 (E)-1-ethyl-5-styrylpyrrolidin-2-one 
• 1109230-90-1 1-ethyl-5-(4-fluorophenyl)-2,3-dihydropyrrole 
• 1109230-89-8 1-ethyl-5-(4-methoxyphenyl)-2,3-dihydropyrrole 
• 1109230-81-0 1-ethyl-5-phenyl-2,3-dihydropyrrole 
• 1109230-92-3 5-(4-bromophenyl)-1-ethyl-2,3-dihydropyrrole 
• 1109230-91-2 5-(4-chlorophenyl)-1-ethyl-2,3-dihydropyrrole 
• 51420-33-8 4-phenylpiperazine-1-carboxaldehyde 
• 2314-78-5 N-ethylsuccinimide 

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