3470-98-2

Basic information

• Product Name: 1-Butylpyrrolidin-2-one
• Synonyms: 1-BUTYL-2-PYRROLIDONE;1-N-BUTYL-2-PYRROLIDONE;N-BUTYL-2-AZACYCLOPENTANONE;1-butyl-2-pyrrolidinon;1-Butyl-2-pyrrolidinone;1-butyl-2-pyrrolidione;N-Butyl-2-pyrrolidinone;N-Butyl-2-pyrrolidone
• CAS NO: 3470-98-2
• Molecular Formula: C₈H₁₅NO
• Molecular Weight: 141.21
• EINECS: 222-437-8
• Product Categories: Pyrrole&Pyrrolidine&Pyrroline
• Mol File: 3470-98-2.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 137 °C / 28mmHg
• Flash Point: 103 °C
• Appearance: corlorless clear liquid
• Density: 0,96 g/cm3
• Vapor Pressure: 0.0315mmHg at 25°C
• Refractive Index: 1.4640 to 1.4660
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly)
• PKA: -0.41±0.20(Predicted)
• Water Solubility: 1000g/L at 20℃
• CAS DataBase Reference: 1-Butylpyrrolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Butylpyrrolidin-2-one(3470-98-2)
• EPA Substance Registry System: 1-Butylpyrrolidin-2-one(3470-98-2)

Safety Data

• Safety Statements: 23-24/25
• RTECS: UY5746000
• Hazardous Substances Data: 3470-98-2(Hazardous Substances Data)

Usage

Chemical Properties

corlorless clear liquid

Flammability and Explosibility

Notclassified

InChI:InChI=1/C8H15NO/c1-2-3-6-9-7-4-5-8(9)10/h2-7H2,1H3

Synthetic route

2-pyrrolidinon (616-45-5) + butyraldehyde (123-72-8) → N-n-butyl-2-pyrrolidinone (3470-98-2)

Conditions	Yield
With hydrogen; sodium sulfate; palladium on activated charcoal In ethyl acetate at 100℃; under 30002.4 Torr; for 4h;	98%
With hydrogen; sodium sulfate; palladium on activated charcoal In ethyl acetate at 100℃; under 30002.4 Torr; for 4h;	98%

2-pyrrolidinon (616-45-5) + n-butyl methanesulfonate (1912-32-9) → N-n-butyl-2-pyrrolidinone (3470-98-2)

Conditions	Yield
With tetraethylammonium tosylate In N,N-dimethyl-formamide electroreduction;	95%

2-pyrrolidinon (616-45-5) + n-Butyl chloride (109-69-3) → N-n-butyl-2-pyrrolidinone (3470-98-2)

Conditions	Yield
With tetraethylammonium tosylate In N,N-dimethyl-formamide electroreduction;	93%

1-(1-butenyl)-pyrrolidone (117593-76-7) → N-n-butyl-2-pyrrolidinone (3470-98-2)

Conditions	Yield
With oxygen; hydrazine hydrate; 7-(trifluoromethyl)-1,10-ethyleneisoalloxazinium chloride In water at 100℃; under 760.051 Torr; for 18h;	93%

2-pyrrolidinon (616-45-5) + 1-bromo-butane (109-65-9) → N-n-butyl-2-pyrrolidinone (3470-98-2)

Conditions	Yield
With N-benzyl-trimethylammonium hydroxide at 20℃; Neat (no solvent); chemoselective reaction;	85%
With tetraethylammonium tosylate In N,N-dimethyl-formamide electroreduction;	55%
With potassium hydroxide 1) DMSO, 100 deg C, 1 h, 2) DMSO, 1 d, RT; Yield given. Multistep reaction;

N-allyl-N-butylamine (4538-09-4) + carbon monoxide (201230-82-2) → N-n-butyl-2-pyrrolidinone (3470-98-2)

Conditions	Yield
With sodium tetrahydroborate; carbonylhydridetris(triphenylphosphine)rhodium(I) In dichloromethane; isopropyl alcohol at 100℃; under 26220 Torr; for 24h;	60%

2-pyrrolidinon (616-45-5) + 1-iodo-butane (542-69-8) → N-n-butyl-2-pyrrolidinone (3470-98-2)

Conditions	Yield
With tetraethylammonium tosylate In N,N-dimethyl-formamide electroreduction;	40%
With sodium hydride Heating;	33%

4-butanolide (96-48-0) + N-butylamine (109-73-9) → N-n-butyl-2-pyrrolidinone (3470-98-2)

Conditions	Yield
at 280℃;
at 300℃;

N-trimethylsilyl-pyrrolidin-2-one (14468-90-7) + 1-iodo-butane (542-69-8) → N-n-butyl-2-pyrrolidinone (3470-98-2)

Conditions	Yield
With tetraethylammonium fluoride 1.) DMF, RT, 20 Torr, 2.) RT; Yield given. Multistep reaction;

cyclobutanone (1191-95-3) + N-butylamine (109-73-9) → N-n-butyl-2-pyrrolidinone (3470-98-2)

Conditions	Yield
With p-nitrobenzenesulfonyl peroxide 1.) -78 deg C, dichloromethane, 2.) 25 deg C; Yield given. Multistep reaction;

2-pyrrolidinon (616-45-5) + n-C4H9X → N-n-butyl-2-pyrrolidinone (3470-98-2)

Conditions	Yield
With sodium hydride at 60 - 70℃;

tetrahydrofuran (109-99-9) + N-(n-butyl)azetidine (3334-92-7) + carbon monoxide (201230-82-2) → poly{[carbonyl(n-butylimino)-1,3-propylene]-co-[(n-butylimino)-1,3-propylene]-co-[carbonyloxy-1,4-butylene]}, Mn 3780 Da, PDI 1.55 by GPC, ester fraction 4.7 percent; monomer(s): tetrahydrofuran; carbon monoxide; N-n-butylazetidine + N-n-butyl-2-pyrrolidinone (3470-98-2)

Conditions	Yield
[cobalt(CH3CO)(CO)3P(o-tolyl)3] at 70℃; under 51714.8 Torr; for 48h;

tetrahydrofuran (109-99-9) + N-(n-butyl)azetidine (3334-92-7) + carbon monoxide (201230-82-2) → poly{[carbonyl(n-butylimino)-1,3-propylene]-co-[(n-butylimino)-1,3-propylene]-co-[carbonyloxy-1,4-butylene]}; monomer(s): tetrahydrofuran; carbon monoxide; N-n-butylazetidine + N-n-butyl-2-pyrrolidinone (3470-98-2)

Conditions	Yield
[cobalt(CH3CO)(CO)3P(o-tolyl)3] at 70℃; under 51714.8 Torr; for 48h;

tetrahydrofuran (109-99-9) + N-(n-butyl)azetidine (3334-92-7) + carbon monoxide (201230-82-2) → poly{[carbonyl(n-butylimino)-1,3-propylene]-co-[(n-butylimino)-1,3-propylene]-co-[carbonyloxy-1,4-butylene]}, Mn 2160 Da, PDI 1.47 by GPC, ester fraction 8.3 percent; monomer(s): tetrahydrofuran; carbon monoxide; N-n-butylazetidine + N-n-butyl-2-pyrrolidinone (3470-98-2)

Conditions	Yield
[cobalt(CH3CO)(CO)3P(o-tolyl)3] at 70℃; under 51714.8 Torr; for 48h;

2-pyrrolidinon (616-45-5) + butan-1-ol (71-36-3) → N-n-butyl-2-pyrrolidinone (3470-98-2)

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

N-butyl-L-glutamic acid (4754-15-8) + N,N-dibutylglutamic acid → 2-pyrrolidinon (616-45-5) + N-n-butyl-2-pyrrolidinone (3470-98-2) + propionic acid (802294-64-0)

Conditions	Yield
With 4.8 wt% Pd/Al2O3 (acidic) In water at 250℃; under 4500.45 Torr; for 6h; Inert atmosphere;	A 18 %Spectr. B 65 %Spectr. C 10 %Spectr.

L-glutamic acid (56-86-0) + butyraldehyde (123-72-8) → 2-pyrrolidinon (616-45-5) + N-n-butyl-2-pyrrolidinone (3470-98-2) + propionic acid (802294-64-0)

Conditions	Yield
Stage #1: L-glutamic acid; butyraldehyde With 4.8 wt% Pd/Al2O3 (acidic); hydrogen at 20℃; under 5625.56 Torr; for 6h; Stage #2: With 4.8 wt% Pd/Al2O3 (acidic) at 250℃; under 4500.45 Torr; for 16h; Inert atmosphere;	A 15 %Spectr. B 65 %Spectr. C 10 %Spectr.

N-butylpyroglutamic acid → 2-pyrrolidinon (616-45-5) + N-n-butyl-2-pyrrolidinone (3470-98-2)

Conditions	Yield
With 4.8 wt% Pd/Al2O3 (acidic) In water at 220℃; under 4500.45 Torr; for 16h; Inert atmosphere;	A 13 %Spectr. B 17 %Spectr.

N-butylpyroglutamic acid → 2-pyrrolidinon (616-45-5) + N-n-butyl-2-pyrrolidinone (3470-98-2) + propionic acid (802294-64-0)

Conditions	Yield
With 4.8 wt% Pd/Al2O3 (acidic) In water at 250℃; under 4500.45 Torr; for 6h; Catalytic behavior; Reagent/catalyst; Inert atmosphere;	A 15 %Spectr. B 63 %Spectr. C 13 %Spectr.

N-butylpyroglutamic acid → N-n-butyl-2-pyrrolidinone (3470-98-2)

Conditions	Yield
With 5.1 wt% Pd/SiO2 In water at 250℃; under 4500.45 Torr; for 6h; Catalytic behavior; Reagent/catalyst; Inert atmosphere;	19 %Spectr.

N-butylpyroglutamic acid → 1-butylpyrrolidine (767-10-2) + N-n-butyl-2-pyrrolidinone (3470-98-2)

Conditions	Yield
With 4.8 wt% Pd/Al2O3 (acidic); hydrogen In water at 250℃; under 11251.1 Torr; for 6h;	A 29 %Spectr. B 17 %Spectr.

monosodium N-butylglutamate → 2-pyrrolidinon (616-45-5) + N-n-butyl-2-pyrrolidinone (3470-98-2) + propionic acid (802294-64-0)

Conditions	Yield
With 4.8 wt% Pd/Al2O3 (acidic) In water at 250℃; under 30003 - 37503.8 Torr; for 6h; Pressure; Inert atmosphere;	A 12 %Spectr. B 35 %Spectr. C 15 %Spectr.

monosodium N-butylglutamate → N-n-butyl-2-pyrrolidinone (3470-98-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: water / 4 h / 210 °C / Inert atmosphere 1.2: Amberlyst® 15 resin (hydrogen form) 2.1: 4.8 wt% Pd/Al2O3 (acidic) / water / 16 h / 220 °C / 4500.45 Torr / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: water / 4 h / 210 °C / Inert atmosphere 1.2: Amberlyst® 15 resin (hydrogen form) 2.1: 4.8 wt% Pd/Al2O3 (acidic) / water / 6 h / 250 °C / 4500.45 Torr / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: water / 4 h / 210 °C / Inert atmosphere 1.2: Amberlyst® 15 resin (hydrogen form) 2.1: 5.1 wt% Pd/SiO2 / water / 6 h / 250 °C / 4500.45 Torr / Inert atmosphere View Scheme

monosodium N-butylglutamate → 1-butylpyrrolidine (767-10-2) + N-n-butyl-2-pyrrolidinone (3470-98-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: water / 4 h / 210 °C / Inert atmosphere 1.2: Amberlyst® 15 resin (hydrogen form) 2.1: hydrogen; 4.8 wt% Pd/Al2O3 (acidic) / water / 6 h / 250 °C / 11251.1 Torr View Scheme

N-n-butyl-2-pyrrolidinone (3470-98-2) + 2-Adamantanone (700-58-3) → 2-(1-butyl-2-oxopyrrolidin-3-yl)tricyclo[3.3.1.13,7]decan-2-ol (913335-88-3)

Conditions	Yield
Stage #1: N-n-butyl-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.;	85%
Stage #1: N-n-butyl-2-pyrrolidinone With lithium diisopropyl amide at -70℃; Stage #2: 2-Adamantanone In tetrahydrofuran at -80℃;

N-n-butyl-2-pyrrolidinone (3470-98-2) + trifluoroacetic anhydride (407-25-0) → (Z)-1-butyl-3-(1-chloro-2,2,2-trifluoroethylidene)pyrrolidin-2-one

Conditions	Yield
With aluminum (III) chloride In N,N-dimethyl-formamide at 60℃; for 24h;	85%

N-n-butyl-2-pyrrolidinone (3470-98-2) + 5-bromo-2-fluorobenzaldehyde (93777-26-5) → 4-(4-bromo-2-formyl-N-butylanilino)-butyric acid (329347-25-3)

Conditions	Yield
Stage #1: N-n-butyl-2-pyrrolidinone With sodium hydroxide for 8h; Heating; Stage #2: With hydrogenchloride Stage #3: 5-bromo-2-fluorobenzaldehyde With sodium carbonate In water; dimethyl sulfoxide Heating; Further stages.;	84%
With sodium carbonate In hydrogenchloride; water; dimethyl sulfoxide	84%

N-n-butyl-2-pyrrolidinone (3470-98-2) + benzoyl chloride (98-88-4) → N-benzoyl-4-(n-butylamino)butyric acid (71455-60-2)

Conditions	Yield
(i) aq. NaOH, (ii) /BRN= 471389/; Multistep reaction;
(i) NaOH, (ii) /BRN= 471389/; Multistep reaction;

N-n-butyl-2-pyrrolidinone (3470-98-2) → 4-(n-Butyl)-aminobuttersaeure (79858-44-9)

Conditions	Yield
With barium dihydroxide

N-n-butyl-2-pyrrolidinone (3470-98-2) → 3-adamantan-2-yl-1-butyl-pyrrolidine

Conditions	Yield
Multi-step reaction with 4 steps 1.1: lithium diisopropylamide / diethyl ether; hexane; tetrahydrofuran / 0.33 h / -80 °C 1.2: 85 percent / diethyl ether; hexane; tetrahydrofuran / -80 - 20 °C 2.1: 80 percent / p-toluenesulfonic acid monohydrate / benzene / Heating 3.1: 99 percent / hydrogen / PtO2 / ethanol / 20 °C / 2068.65 Torr 4.1: 72 percent / LiAlH4 / tetrahydrofuran / 25 h / Heating View Scheme
Multi-step reaction with 4 steps 1.1: LDA / -70 °C 1.2: tetrahydrofuran / -80 °C 2.1: TsOH / benzene / Heating 3.1: 100 percent / H2 / PtO2 / ethanol / 20 °C / 2068.59 Torr 4.1: LiAlH4 / Heating View Scheme

N-n-butyl-2-pyrrolidinone (3470-98-2) → 1-butyl-3-(tricyclo[3.3.1.13,7]dec-2-yl)-2-pyrrolidinone (372945-58-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: lithium diisopropylamide / diethyl ether; hexane; tetrahydrofuran / 0.33 h / -80 °C 1.2: 85 percent / diethyl ether; hexane; tetrahydrofuran / -80 - 20 °C 2.1: 80 percent / p-toluenesulfonic acid monohydrate / benzene / Heating 3.1: 99 percent / hydrogen / PtO2 / ethanol / 20 °C / 2068.65 Torr View Scheme
Multi-step reaction with 3 steps 1.1: LDA / -70 °C 1.2: tetrahydrofuran / -80 °C 2.1: TsOH / benzene / Heating 3.1: 100 percent / H2 / PtO2 / ethanol / 20 °C / 2068.59 Torr View Scheme

N-n-butyl-2-pyrrolidinone (3470-98-2) → 1-butyl-3-(tricyclo[3.3.1.13,7]dec-2-ylidene)-2-pyrrolidinone (372945-51-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: lithium diisopropylamide / diethyl ether; hexane; tetrahydrofuran / 0.33 h / -80 °C 1.2: 85 percent / diethyl ether; hexane; tetrahydrofuran / -80 - 20 °C 2.1: 80 percent / p-toluenesulfonic acid monohydrate / benzene / Heating View Scheme
Multi-step reaction with 2 steps 1.1: LDA / -70 °C 1.2: tetrahydrofuran / -80 °C 2.1: TsOH / benzene / Heating View Scheme

N-n-butyl-2-pyrrolidinone (3470-98-2) → methyl 7-bromo-1-butyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate (313728-95-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: aq. NaOH / 8 h / Heating 1.2: cc. HCl 1.3: 84 percent / Na2CO3 / dimethylsulfoxide; H2O / Heating 2.1: K2CO3 / dimethylformamide / 2 h / 20 °C 2.2: 81 percent / NaOMe / methanol; various solvent(s) / 0.5 h / 50 °C View Scheme

N-n-butyl-2-pyrrolidinone (3470-98-2) → N-butyl-4-hydroxybutan-1-amine (4543-95-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. Ba(OH)2 2: LiAlH4 / diethyl ether View Scheme

N-n-butyl-2-pyrrolidinone (3470-98-2) → 4-Butylamino-1-butanol-1-D2 (117943-01-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. Ba(OH)2 2: LiAlD4 / tetrahydrofuran View Scheme

N-n-butyl-2-pyrrolidinone (3470-98-2) → N-Butyl-N-(4-p-toluolsulfonoxybutyl)-p-toluolsulfonamid

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. Ba(OH)2 2: LiAlH4 / diethyl ether 3: Py View Scheme

N-n-butyl-2-pyrrolidinone (3470-98-2) → N-Butyl-N-(4-p-toluolsulfonoxybutyl)-p-toluolsulfonamid-4-d(2) (115294-36-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. Ba(OH)2 2: LiAlD4 / tetrahydrofuran 3: Py View Scheme

N-n-butyl-2-pyrrolidinone (3470-98-2) + 4-chloro-3-(difluoromethyl)aniline (66351-92-6) → 1-butyl-2-(4-chloro-3-difluoromethylphenyl)-iminopyrrolidine

Conditions	Yield
With sodium hydroxide; trichlorophosphate In chloroform; water; toluene

Upstream product

• 96-48-0 4-butanolide 
• 109-73-9 N-butylamine 
• 616-45-5 2-pyrrolidinon 
• 109-65-9 1-bromo-butane 
• 542-69-8 1-iodo-butane 
• 109-69-3 n-Butyl chloride 
• 1912-32-9 n-butyl methanesulfonate 
• 56-86-0 L-glutamic acid 
• 123-72-8 butyraldehyde 
• 4754-15-8 N-butyl-L-glutamic acid 
• 117593-76-7 N-butenylpyrrolidone 
• 71-36-3 butan-1-ol 
• 109-99-9 tetrahydrofuran 
• 3334-92-7 N-(n-butyl)azetidine 

Downstream Products

• 616-45-5 2-pyrrolidinon 
• 802294-64-0 propionic acid 
• 115294-36-5 N-Butyl-N-(4-p-toluolsulfonoxybutyl)-p-toluolsulfonamid-4-d⁽²⁾ 
• 329347-25-3 4-(4-bromo-2-formyl-N-butylanilino)-butyric acid 
• 71455-60-2 N-benzoyl-4-(n-butylamino)butyric acid 

Relevant articles and documents

Cobalt-catalyzed carbonylative copolymerization of N-alkylazetidines and tetrahydrofuran

(Chemical Equation Presented) A living polymerization: Poly(amide-coester)s with either gradient or segmental ester distribution are formed by the cobalt-catalyzed polymerization of azetidine in THF in the absence or presence of Lil, respectively. Periodic addition of azetidine results in copolymers with multiple amide blocks separated by ester segments (see picture). The polymers undergo a two-stage chemical degradation.

Organocatalytic diimide reduction of enamides in water

Bridged flavinium organocatalysts have displayed efficacy in the diimide mediated reduction of enamides in aqueous conditions. This represents the first diimide reduction of an electron rich alkene and offers a clean alternative to the use of alkylating agents for N-alkylation.

Triton B-mediated mild, convenient, and efficient method for the selective alkylation of cyclic secondary amines and thiols

Alkylation of cyclic secondary amines, thiols, and pyridazinones has been demonstrated with alkyl halides using Triton B as base and reaction medium.