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1-Methyl-2-pyrrolidinone

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Name

1-Methyl-2-pyrrolidinone

EINECS 212-828-1
CAS No. 872-50-4 Density 1.033
PSA 20.31000 LogP 0.17650
Solubility Water solubility: >=10 g/100 mL at 20 °C Melting Point -24 °C
Formula C5H9NO Boiling Point 201.999 °C at 760 mmHg
Molecular Weight 99.15 Flash Point 86.111 °C
Transport Information Appearance colourless or light yellow liquid with an amine odour
Safety 41 Risk Codes 45-65-36/38
Molecular Structure Molecular Structure of 872-50-4 (1-Methyl-2-pyrrolidinone) Hazard Symbols ToxicT,IrritantXi
Synonyms

2-Pyrrolidinone,1-methyl-;1-Methyl-5-pyrrolidinone;1-Methylazacyclopentan-2-one;1-Methylpyrrolidone;AgsolEx 1;M-Pyrol;Microposit 2001;N 0131;N-Methyl-2-ketopyrrolidine;N-Methyl-2-pyrrolidinone;N-Methyl-a-pyrrolidinone;N-Methylbutyrolactam;N-Methylpyrrolidone;NMP;NSC 4594;Pharmasolve;Pyrol M;SL 1332;N-Methyl-2-Pyrrolidone(NMP);N-methyl-pyrrolidone;

 

1-Methyl-2-pyrrolidinone Synthetic route

96-48-0

4-butanolide

methylamine

methylamine

Conditions
ConditionsYield
With water; ZSM-5 at 280℃;99%
In water at 300℃; under 75007.5 Torr; Concentration;99.9%
at 255℃; under 15001.5 Torr; for 3h;98.2%
33693-57-1

3-bromo-1-methyl-pyrrolidin-2-one

872-50-4

1-methyl-pyrrolidin-2-one

Conditions
ConditionsYield
With indium; water at 20℃; for 6h;99%
120-94-5

1-Methylpyrrolidine

872-50-4

1-methyl-pyrrolidin-2-one

Conditions
ConditionsYield
With 5.4 wt% Au/CeO2; water; oxygen In 1,4-dioxane at 80℃; under 760.051 Torr; for 3.5h; Catalytic behavior; Reagent/catalyst; Temperature; Concentration; Schlenk technique;97%
With iodosylbenzene In water for 36h;55%
With tert.-butylhydroperoxide; [Mn(GBOA)2(H2O)2]*(Cl)2*4H2O In acetonitrile at 50 - 55℃;49.4%
With carbonylchlorohydrido(4,5-bis((diisopropylphosphino)methyl)acridine)ruthenium(II); water; sodium hydroxide at 160℃; for 48h; Inert atmosphere; Schlenk technique;22%
With water; oxygen at 80℃; under 760.051 Torr; for 24h; Green chemistry; regioselective reaction;> 99 %Chromat.
1191-95-3

cyclobutanone

85462-16-4

N-Methyl-O-p-nitrophenylsulphonylhydroxylamine

872-50-4

1-methyl-pyrrolidin-2-one

Conditions
ConditionsYield
In chloroform 1.) -78 deg C, 2.) 25 deg C;96%
In chloroform at 25℃;96%
In chloroform at 25℃; other ketones, also with ketals, other reagent, other solvent;96%
96-48-0

4-butanolide

124-40-3

dimethyl amine

74-89-5

methylamine

75-50-3

trimethylamine

872-50-4

1-methyl-pyrrolidin-2-one

Conditions
ConditionsYield
at 255℃; for 3h;94.8%
616-45-5

2-pyrrolidinon

124-38-9

carbon dioxide

872-50-4

1-methyl-pyrrolidin-2-one

Conditions
ConditionsYield
With copper nanoparticles-decorated triazinetriamine derived porous organic polymer; polymethylhydrosiloxane In acetonitrile at 80℃; under 760.051 Torr; for 8h; Inert atmosphere;94%
76128-61-5

1-(dimethylchlorosilylmethyl)-2-pyrrolidone

A

872-50-4

1-methyl-pyrrolidin-2-one

B

diisopropoxydimethylsilane

diisopropoxydimethylsilane

Conditions
ConditionsYield
With sodium isopropylate In isopropyl alcohol at 60℃; for 3h;A 92%
B 92%
1-Methyl-2,2-dipropoxy-pyrrolidine

1-Methyl-2,2-dipropoxy-pyrrolidine

2-Benzyl-1,2,3,4,6,7,12,12a-octahydropyrazino<2',1':6,1>pyrido<3,4-b>indole
79108-52-4

2-Benzyl-1,2,3,4,6,7,12,12a-octahydropyrazino<2',1':6,1>pyrido<3,4-b>indole

A

872-50-4

1-methyl-pyrrolidin-2-one

B

2-Benzyl-7-propyl-1,2,3,4,6,7,12,12a-octahydro-pyrazino[1',2':1,6]pyrido[3,4-b]indole

2-Benzyl-7-propyl-1,2,3,4,6,7,12,12a-octahydro-pyrazino[1',2':1,6]pyrido[3,4-b]indole

Conditions
ConditionsYield
In tetrahydrofuran at 35℃; for 6h;A n/a
B 90%
79108-53-5

1-Methyl-2,2-dipropoxy-pyrrolidine

42021-34-1

Biriperone

A

872-50-4

1-methyl-pyrrolidin-2-one

B

79108-61-5

1-(4-Fluoro-phenyl)-4-(7-propyl-3,4,6,7,12,12a-hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl)-butan-1-one

Conditions
ConditionsYield
In tetrahydrofuran at 35℃; for 6h;A n/a
B 90%
42021-34-1

Biriperone

39650-82-3

2,2-dimethoxy-1-methylpyrrolidine

A

872-50-4

1-methyl-pyrrolidin-2-one

B

79108-56-8

1-(4-Fluoro-phenyl)-4-(7-methyl-3,4,6,7,12,12a-hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl)-butan-1-one

Conditions
ConditionsYield
In tetrahydrofuran at 35℃; for 6h;A n/a
B 90%
1119-48-8

4-(methylamino)butyric acid

872-50-4

1-methyl-pyrrolidin-2-one

Conditions
ConditionsYield
With titanium tetrakis(trimethylsilanolate) at 120℃; for 1h; Reagent/catalyst; Temperature; Solvent; Ionic liquid; Inert atmosphere;88%
With titanium(IV) isopropylate In 1,2-dichloro-ethane for 5h; Heating;85%
79108-52-4

2-Benzyl-1,2,3,4,6,7,12,12a-octahydropyrazino<2',1':6,1>pyrido<3,4-b>indole

39650-82-3

2,2-dimethoxy-1-methylpyrrolidine

A

872-50-4

1-methyl-pyrrolidin-2-one

B

79108-54-6

2-Benzyl-7-methyl-1,2,3,4,6,7,12,12a-octahydropyrazino<2',1':6,1>pyrido<3,4-b>indole

Conditions
ConditionsYield
In tetrahydrofuran at 35℃; for 6h;A n/a
B 88%
96-48-0

4-butanolide

124-40-3

dimethyl amine

A

872-50-4

1-methyl-pyrrolidin-2-one

B

67-56-1

methanol

Conditions
ConditionsYield
With water; ZSM-5 at 280℃;A 88%
B 10%
Y-type zeoliteA 51%
B 6.6%
616-45-5

2-pyrrolidinon

80-43-3

bis(1-methyl-1-phenylethyl)peroxide

872-50-4

1-methyl-pyrrolidin-2-one

Conditions
ConditionsYield
With copper(l) chloride In chlorobenzene at 130℃; for 12h; Schlenk technique; Inert atmosphere;87%
35197-40-1

N-methyl-2-pyrrolidone oxime

872-50-4

1-methyl-pyrrolidin-2-one

Conditions
ConditionsYield
With selenium(IV) oxide In toluene Heating;86%
826-41-5

N-Methyl-2,2-diethoxypyrrolidine

42021-34-1

Biriperone

A

872-50-4

1-methyl-pyrrolidin-2-one

B

79108-59-1

4-(7-Ethyl-3,4,6,7,12,12a-hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl)-1-(4-fluoro-phenyl)-butan-1-one

Conditions
ConditionsYield
In tetrahydrofuran at 35℃; for 6h;A n/a
B 85%
110-16-7

maleic acid

74-89-5

methylamine

872-50-4

1-methyl-pyrrolidin-2-one

Conditions
ConditionsYield
With hydrogen; ruthenium (III) acetylacetonate; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In water at 250℃; under 31029.7 - 51716.2 Torr; Product distribution / selectivity;83.5%
72593-14-7

4-Chloro-N-[2-(3,4,6,7,12,12a-hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl)-ethyl]-benzamide

39650-82-3

2,2-dimethoxy-1-methylpyrrolidine

A

872-50-4

1-methyl-pyrrolidin-2-one

B

79108-57-9

4-Chloro-N-[2-(7-methyl-3,4,6,7,12,12a-hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl)-ethyl]-benzamide

Conditions
ConditionsYield
In tetrahydrofuran at 35℃; for 6h;A n/a
B 83%
31282-95-8

1-(chloromethyl)pyrrolidin-2-one

1066-35-9

dimethylmonochlorosilane

872-50-4

1-methyl-pyrrolidin-2-one

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate for 10h; Heating;82%
With trimethylsilyl trifluoromethanesulfonate for 10h; Heating; other substrates, other reagents;82%
21744-74-1

4-methyl-4H-benzo[1,4]oxazin-3-thione

872-50-4

1-methyl-pyrrolidin-2-one

Conditions
ConditionsYield
With manganese(IV) oxide In chloroform for 12h; Ambient temperature;82%
10441-57-3

1-methyl-pyrrolidine-2-thione

872-50-4

1-methyl-pyrrolidin-2-one

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 2h;82%
With tetrabutylammonium periodite In dichloromethane at 20℃; for 2h;81%
With hydrogenchloride; N-methyl-N-nitrosoaniline; potassium iodide In dichloromethane; water at 22℃; for 2.5h;72%
826-41-5

N-Methyl-2,2-diethoxypyrrolidine

72593-14-7

4-Chloro-N-[2-(3,4,6,7,12,12a-hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl)-ethyl]-benzamide

A

872-50-4

1-methyl-pyrrolidin-2-one

B

79108-60-4

4-Chloro-N-[2-(7-ethyl-3,4,6,7,12,12a-hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl)-ethyl]-benzamide

Conditions
ConditionsYield
In tetrahydrofuran at 35℃; for 6h;A n/a
B 80%
826-41-5

N-Methyl-2,2-diethoxypyrrolidine

79108-52-4

2-Benzyl-1,2,3,4,6,7,12,12a-octahydropyrazino<2',1':6,1>pyrido<3,4-b>indole

A

872-50-4

1-methyl-pyrrolidin-2-one

B

79108-58-0

2-Benzyl-7-ethyl-1,2,3,4,6,7,12,12a-octahydro-pyrazino[1',2':1,6]pyrido[3,4-b]indole

Conditions
ConditionsYield
In tetrahydrofuran at 35℃; for 6h;A n/a
B 79%
96-48-0

4-butanolide

75-50-3

trimethylamine

A

1-methyl-pyrrolidin-2-one

1-methyl-pyrrolidin-2-one

B

Conditions
ConditionsYield
ZSM-5A 79%
B 8%

872-50-4

1-methyl-pyrrolidin-2-one

Conditions
ConditionsYield
With tetraethylammonium bromide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile at 20 - 60℃;78%
76596-19-5

1-<(trimethylsilyl)methyl>-2-pyrrolidinone

872-50-4

1-methyl-pyrrolidin-2-one

Conditions
ConditionsYield
With acrylic acid methyl ester In acetonitrile for 17h; Irradiation; Inert atmosphere;77%

C5H10NO2(1-)*K(1+)

872-50-4

1-methyl-pyrrolidin-2-one

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; bis(trichloromethyl) carbonate; potassium hydroxide In water; acetonitrile at 60℃; for 0.00277778h; Inert atmosphere;76%
2374-69-8

butane-1-sulfonic acid methyl ester

14468-90-7

N-trimethylsilyl-pyrrolidin-2-one

A

872-50-4

1-methyl-pyrrolidin-2-one

B

72500-12-0

Trimethylsilyl-1-butansulfonat

Conditions
ConditionsYield
Heating;A 72%
B 75%
79108-53-5

1-Methyl-2,2-dipropoxy-pyrrolidine

55344-34-8

2-(2-Pyridin-4-yl-ethyl)-1,2,3,4,6,7,12,12a-octahydro-pyrazino[1',2':1,6]pyrido[3,4-b]indole

A

872-50-4

1-methyl-pyrrolidin-2-one

B

79123-19-6

7-Propyl-2-(2-pyridin-4-yl-ethyl)-1,2,3,4,6,7,12,12a-octahydro-pyrazino[1',2':1,6]pyrido[3,4-b]indole

Conditions
ConditionsYield
In tetrahydrofuran at 35℃; for 6h;A n/a
B 74%
872-50-4

1-methyl-pyrrolidin-2-one

Conditions
ConditionsYield
With 2,6-dichloropyridine N-oxide; dichloro(5,10,15,20-tetramesitylporphyrinato)ruthenium(IV) In benzene at 40℃;91%
With pyridine; N-hydroxyphthalimide; sodium perchlorate In acetonitrile controlled potential electrolysis, electrodes: glassy-carbon vs. SCE;81%
With silver tetrafluoroborate; water; Selectfluor In acetone at 40℃; for 1h; Schlenk technique; Inert atmosphere;81%

1-Methyl-2-pyrrolidinone Consensus Reports

Reported in EPA TSCA Inventory.

1-Methyl-2-pyrrolidinone Standards and Recommendations

DFG MAK: 19 ppm (80 mg/m3)

1-Methyl-2-pyrrolidinone Specification

1-Methyl-2-pyrrolidinone, its cas register number is 872-50-4. It also can be called N-Methyl-2-pyrrolidinone ; N-Methyl-2-Pyrrolidone ; NMP ; and N-Methylpyrrolidone . It is hazardous, so the first aid measures and others should be known. In addition, N-methyl-pyrrolidone (CAS NO.872-50-4) could be stable at room temperature in closed containers under normal storage and handling conditions. It is not compatible with strong oxidizing agents, strong acids, strong bases, and you must not take it with incompatible materials, light, temperatures above 100 °C, exposure to moist air or water. And also prevent it to broken down into hazardous decomposition products: nitrogen oxides, carbon monoxide, carbon dioxide.

Physical properties about 1-Methyl-2-pyrrolidinone are: (1)ACD/LogP: -0.637; (2)ACD/LogD (pH 5.5): -0.64; (3)ACD/LogD (pH 7.4): -0.64; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 10.73; (7)ACD/KOC (pH 7.4): 10.73; (8)#H bond acceptors: 2; (9)Index of Refraction: 1.47; (10)Molar Refractivity: 26.852 cm3; (11)Molar Volume: 96.268 cm3; (12)Polarizability: 10.645 10-24cm3; (13)Surface Tension: 33.7919998168945 dyne/cm; (14)Density: 1.03 g/cm3; (15)Flash Point: 86.111 °C; (16)Enthalpy of Vaporization: 43.821 kJ/mol; (17)Boiling Point: 201.999 °C at 760 mmHg; (18)Vapour Pressure: 0.29899999499321 mmHg at 25°C

Preparation of 1-Methyl-2-pyrrolidinone: 1-Methyl-2-pyrrolidinone (CAS NO.872-50-4) can be derived by the reaction of Γ-butyrolactone with amine .

Uses of 1-Methyl-2-pyrrolidinone: 1-Methyl-2-pyrrolidinone is used as intermediate for the synthesis of pharmaceuticals, agrochemicals, plasticizers, textile auxiliaries, stabilizers. It is also widely used in oil refining, pigments and cleaning, high polymer synthesis, chemicals, insulation materials, etc.

When you are using this chemical, please be cautious about it as the following:
1. In case of fire and/or explosion do not breathe fumes
2. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
3. Avoid exposure - obtain special instruction before use

You can still convert the following datas into molecular structure:
(1)InChI=1S/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3;
(2)InChIKey=SECXISVLQFMRJM-UHFFFAOYSA-N;
(3)SmilesC1(=O)N(CCC1)C;

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 63300ug/kg (63.3mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987.
mouse LD50 intraperitoneal 3050mg/kg (3050mg/kg)   United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-1087-0695,
mouse LD50 intravenous 54500ug/kg (54.5mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987.
mouse LD50 oral 5130mg/kg (5130mg/kg)   United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-1087-0695,
rabbit LD50 skin 8gm/kg (8000mg/kg)   Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 84, 1974.
rat LCLo inhalation 1gm/m3 (1000mg/m3)   National Technical Information Service. Vol. OTS0534725,
rat LD50 intraperitoneal 2472mg/kg (2472mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 1581, 1976.
 
rat LD50 intravenous 80500ug/kg (80.5mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987.
rat LD50 oral 3914mg/kg (3914mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 1581, 1976.
 
rat LD50 subcutaneous > 2gm/kg (2000mg/kg)   United States Patent Document. Vol. #4882359,
rat LD50 unreported 7gm/kg (7000mg/kg)   "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 408, 1969.

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