1-METHYL-2-PYRROLIDONE

1-Methyl-2-pyrrolidone is a member of the class of pyrrolidine-2-ones that is pyrrolidin-2-one in which the hydrogen attached to the nitrogen is replaced by a methyl group. 
1-Methyl-2-pyrrolidone has a role as a polar aprotic solvent. 
1-Methyl-2-pyrrolidone is a N-alkylpyrrolidine, a lactam and a member of pyrrolidin-2-ones.

CAS:    872-50-4
MF:    C5H9NO
MW:    99.13
EINECS:    212-828-1

1-Methyl-2-pyrrolidone appears as a clear colorless liquid with a "fishlike" odor. 
Denser than water. 
Flash point 199 °F. 
Contact may irritate skin, eyes and mucous membranes. 
May be toxic by ingestion.
1-Methyl-2-pyrrolidone is a member of the class of pyrrolidine-2-ones that is pyrrolidin-2-one in which the hydrogen attached to the nitrogen is replaced by a methyl group. 
1-Methyl-2-pyrrolidone has a role as a polar aprotic solvent. 
1-Methyl-2-pyrrolidone is a N-alkylpyrrolidine, a lactam and a member of pyrrolidin-2-ones.
Stable to air and moisture; incompatible with strong acids, bases, or oxidants (forms hydrogen upon decomposition); generally considered non-toxic, however thorough toxicity studies have not been performed; skin/eye contact and inhalation should be avoided.

1-Methyl-2-pyrrolidone is hygroscopic (picks up moisture) but stable under normal conditions. 
1-Methyl-2-pyrrolidone will violently react with strong oxidizers such as hydrogen peroxide, nitric acid, sulfuric acid, etc.
The primary decomposition products produce carbon monoxide and nitrogen oxide fumes. 
Excessive exposure or spillage should be avoided as a matter of good practice. 
Lyondell Chemical Company recommends wearing butyl gloves when using 1-Methyl-2-pyrrolidone. 
1-Methyl-2-pyrrolidone should be stored in clean, phenolic-lined mild steel or alloy drums. 

1-Methyl-2-pyrrolidone is a powerful, aprotic solvent with high solvency, and low volatility. 
This colorless, high boiling, high flash point and low vapor pressure liquid carries a mild amine-like odor. 
1-Methyl-2-pyrrolidone has high chemical and thermal stability and is completely miscible with water at all temperatures. 
1-Methyl-2-pyrrolidone can serve as a co-solvent with water, alcohols, glycol ethers, ketones, and aromatic/chlorinated hydrocarbons. 
1-Methyl-2-pyrrolidone is both recyclable by distillation and readily biodegradable. 
1-Methyl-2-pyrrolidone is not found on the Hazardous Air Pollutants (HAPs) list of the 1990 Clean Air Act Amendments.

1-Methyl-2-pyrrolidone is an organic compound consisting of a 5-membered lactam. 
1-Methyl-2-pyrrolidone is a colorless liquid, although impure samples can appear yellow. 
1-Methyl-2-pyrrolidone is miscible with water and with most common organic solvents. 
1-Methyl-2-pyrrolidone also belongs to the class of dipolar aprotic solvents such as dimethylformamide and dimethyl sulfoxide. 
1-Methyl-2-pyrrolidone is used in the petrochemical, polymer and battery industries as a solvent, exploiting its nonvolatility and ability to dissolve diverse materials (including polyvinylidene difluoride, PVDF).

1-Methyl-2-pyrrolidone Chemical Properties
Melting point: -24 °C (lit.)
Boiling point: 202 °C (lit.) 81-82 °C/10 mmHg (lit.)
Density: 1.028 g/mL at 25 °C (lit.)
Vapor density: 3.4 (vs air)
Vapor pressure: 0.29 mm Hg ( 20 °C)
Refractive index: n20/D 1.479
Fp: 187 °F
Storage temp.: Store at +5°C to +30°C.
Solubility: ethanol: miscible0.1ML/mL, clear, colorless (10%, v/v)
Form: Liquid
pka: -0.41±0.20(Predicted)
Color: ≤20(APHA)
PH: 8.5-10.0 (100g/l, H2O, 20℃)
Odor: Slight amine odor
PH Range: 7.7 - 8.0
Explosive limit: 1.3-9.5%(V)
Water Solubility: >=10 g/100 mL at 20 ºC
Sensitive: Hygroscopic
λmax: 283nm(MeOH)(lit.)
Merck: 14,6117
BRN: 106420
Stability: Stable, but decomposes upon exposure to light. 
Combustible. 
Incompatible with strong oxidizing agents, strong acids, reducing agents, bases.
InChIKey: SECXISVLQFMRJM-UHFFFAOYSA-N
LogP: -0.46 at 25℃
CAS DataBase Reference: 872-50-4(CAS DataBase Reference)
NIST Chemistry Reference: 2-Pyrrolidinone, 1-methyl-(872-50-4)
EPA Substance Registry System: N-Methyl-2-pyrrolidone (872-50-4)

1-Methyl-2-pyrrolidone is a colourless or light yellow liquid with an amine odour. 
1-Methyl-2-pyrrolidone can undergo a number of chemical reactions even though it is accepted as a stable solvent. 
1-Methyl-2-pyrrolidone is resistant to hydrolysis under neutral conditions, but strong acid or base treatment results in ring opening to 4-methyl aminobutyric acid. 
1-Methyl-2-pyrrolidone can be reduced to 1-methyl pyrrolidine with borohydride. 
Treatment with chlorinating agents results in amide formation,an intermediate which can undergo further substitution, while treatment with amyl nitrate yields the nitrate. 
Olefins can be added to the 3 position by treatment first with oxalic esters, then with appropriate aldehyes.

Uses    
1-Methyl-2-pyrrolidone is a polar aprotic solvent that has the advantages of low toxicity, high boiling point, outstanding solvency, strong selectivity and good stability.
1-Methyl-2-pyrrolidone is widely used in purification of aromatic hydrocarbon extraction, acetylene, olefins, and diolefins.
1-Methyl-2-pyrrolidone is used in industrial cleaning, and it serves as a solvent for production of pesticides, engineering plastics, coatings, synthetic fibers, and integrated circuits.
1-Methyl-2-pyrrolidone can also be used as an industrial cleanser, dispersant, dye, lubricant and antifreeze.
1-Methyl-2-pyrrolidone is an excellent solvent, widely used in aromatics extraction, lubricating oil refining, acetylene enrichment, butadiene separation and synthesis gas desulfurization.

1-Methyl-2-pyrrolidone is used in gas desulfurization, lubricating oil refining, lubricating oil antifreeze, olefin extraction, and as a solvent for insoluble engineering plastics polymerization.
1-Methyl-2-pyrrolidone can be used in herbicide, to clean insulation materials, semiconductor industry precision instruments and circuit boards, to recycle PVC exhaust, as a detergent, dye supplement and dispersing agent.
1-Methyl-2-pyrrolidone is used in mediums for polymerization reactions such as engineering plastics and aramid fiber.
1-Methyl-2-pyrrolidone is used as a polyvinylidene fluoride solvent and electrode auxiliary material for lithium ion batteries.
high purity grade for ICP-MS detection.

1) 1-Methyl-2-pyrrolidone is used as a general dipolar aprotic solvent, stable and unreactive;
2) for extraction of aromatic hydrocarbons from lubricating oils;
3) for carbon dioxide removal in ammonia generators;
4) as a solvent for polymerization reactions and polymers;
5) as a paint stripper;
6) for pesticide formulations.
Other non-industrial uses of 1-Methyl-2-pyrrolidone are based on its properties as a dissociating solvent suitable for electrochemical and physical chemical studies. 
Pharmaceutical applications make use of the properties of 1-Methyl-2-pyrrolidone as a penetration enhancer for a more rapid transfer of substances through the skin. 
1-Methyl-2-pyrrolidone has been approved as a solvent for slimicide application to food packaging materials.

1-Methyl-2-pyrrolidone is used to recover certain hydrocarbons generated in the processing of petrochemicals, such as the recovery of 1,3-butadiene and acetylene. 
1-Methyl-2-pyrrolidone is used to absorb hydrogen sulfide from sour gas and hydrodesulfurization facilities. 
1-Methyl-2-pyrrolidone's good solvency properties have led to NMP's use to dissolve a wide range of polymers. 
Specifically, 1-Methyl-2-pyrrolidone is used as a solvent for surface treatment of textiles, resins, and metal coated plastics or as a paint stripper. 
1-Methyl-2-pyrrolidone is also used as a solvent in the commercial preparation of polyphenylene sulfide. 
In the pharmaceutical industry, 1-Methyl-2-pyrrolidone is used in the formulation for drugs by both oral and transdermal delivery routes.
1-Methyl-2-pyrrolidone is also used heavily in lithium ion battery fabrication, as a solvent for electrode preparation, because 1-Methyl-2-pyrrolidone has a unique ability to dissolve polyvinylidene fluoride binder. 
Due to 1-Methyl-2-pyrrolidone's toxicity and high boiling point, there is much effort to replace it in battery manufacturing with other solvent(s), like water.

Metabolism    
Male Sprague-Dawley rats were given a single intraperitoneal injection (45 mg/kg) of radiolabeled 1-Methyl-2-pyrrolidone. 
Plasma levels of radioactivity and compound were monitored for six hours and the results suggested a rapid distribution phase which was followed by a slow elimination phase. 
The major amount of label was excreted in the urine within 12 hours and accounted for approximately 75% of the labelled dose. 
Twenty-four hours after dosage, cumulative excretion (urine) was approximately 80% of the dose. 
Both ring- and methyl-labeled species were used, as well as both [14C]- and [3H]-labeled 1-Methyl-2-pyrrolidone. 

The initial labeled ratios were maintained during the first 6 hours after dosage. 
After 6 hours, the liver and intestines were found to contain the highest accumulations of radioactivity, approximately 2-4% of the dose. 
Little radioactivity was noted in the bile or respired air. 
High performance liquid chromatography of urine showed the presence of one major and two minor metabolites. 
The major metabolite (70-75% of the administered radioactive dose) was analyzed by liquid chromatography-mass spectrometry and gas chromatography-mass spectrometry and was proposed to be a 3- or 5-hydroxy-l-methyl-2-pyrrolidone (Wells 1987).

Health hazards
1-Methyl-2-pyrrolidone is an agent that causes the production of physical defects in the developing embryo.
1-Methyl-2-pyrrolidone also is a reproductive toxin, a chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. 
Reproductive toxicity includes developmental effects.
1-Methyl-2-pyrrolidone can be absorbed into the body by inhalation, through the skin and by ingestion. 
When people are exposed to 1-Methyl-2-pyrrolidone, rapid, irregular respiration, shortness of breath, decreased pain reflex, and slight bloody nasal secretion are possible.
Inhalation can result in headaches and exposure on skin can result in redness and pain.
When ingested 1-Methyl-2-pyrrolidone will cause a burning sensation in the throat and chest. 
1-Methyl-2-pyrrolidone also can cause an acute solvent syndrome.

Biological aspects
In rats, 1-Methyl-2-pyrrolidone is absorbed rapidly after inhalation, oral, and dermal administration, distributed throughout the organism, and eliminated mainly by hydroxylation to polar compounds, which are excreted via urine. 
About 80% of the administered dose is excreted as 1-Methyl-2-pyrrolidone and NMP metabolites within 24 hours. 
A probably dose dependent yellow coloration of the urine in rodents is observed. 
The major metabolite is 5-hydroxy-N-methyl-2-pyrrolidone.

Studies in humans show comparable results. 
Dermal penetration through human skin has been shown to be very rapid. 
1-Methyl-2-pyrrolidone is rapidly biotransformed by hydroxylation to 5-hydroxy-N-methyl-2-pyrrolidone, which is further oxidized to N-methylsuccinimide; this intermediate is further hydroxylated to 2-hydroxy-N-methylsuccinimide. 
These metabolites are all colourless. 
The excreted amounts of 1-Methyl-2-pyrrolidone metabolites in the urine after inhalation or oral intake represented about 100% and 65% of the administered doses, respectively. 
1-Methyl-2-pyrrolidone has a low potential for skin irritation and a moderate potential for eye irritation in rabbits. 
Repeated daily doses of 450 mg/kg body weight administered to the skin caused painful and severe haemorrhage and eschar formation in rabbits. 
These adverse effects have not been seen in workers occupationally exposed to pure 1-Methyl-2-pyrrolidone, but they have been observed after dermal exposure to 1-Methyl-2-pyrrolidone used in cleaning processes. 
No sensitization potential has been observed.

Synonyms
1-METHYL-2-PYRROLIDINONE
872-50-4
N-Methylpyrrolidone
N-Methyl-2-pyrrolidone
1-methylpyrrolidin-2-one
1-Methyl-2-pyrrolidone
Methylpyrrolidone
N-Methyl-2-pyrrolidinone
M-Pyrol
N-Methylpyrrolidinone
1-Methylpyrrolidinone
1-Methylpyrrolidone
Methyl pyrrolidone
2-Pyrrolidinone, 1-methyl-
n-methyl-pyrrolidone
1-Methyl-5-pyrrolidinone
1-Methylazacyclopentan-2-one
N-methylpyrrolidin-2-one
NMP
N-Methyl-gamma-butyrolactam
N-methyl pyrrolidone
1-methylpyrrolidine-2-one
N-methyl pyrrolidinone
Methyl-2-pyrrolidinone
1-methyl-2-pyrrolidon
Methylpyrrolidinone
2-Pyrrolidinone, methyl-
Methylpyrrolidone [NF]
N-Methylpyrrolid-2-one
N-Methyl-alpha-pyrrolidone
NSC 4594
Agsolex 1
2687-44-7
N-Methyl-alpha-pyrrolidinone
51013-18-4
NSC-4594
MFCD00003193
JR9CE63FPM
1-methyl-pyrrolidin-2-one
N-Methyl-.alpha.-pyrrolidone
CHEMBL12543
N-Methyl-.gamma.-butyrolactam
CHEBI:7307
N-Methyl-.alpha.-pyrrolidinone
DTXSID6020856
1-Methyl-2-pyrrolidinone, anhydrous
1-Methyl-2-pyrrolidinone, HPLC Grade
N 0131
26876-92-6
N-methyl-pyrrolidinone
pharmasolve
N-Methylpyrrolidon
CAS-872-50-4
CCRIS 1633
Methylpyrrolidone, N-
HSDB 5022
Pyrrolidinone, methyl-
N-Methyl-2-pyrrolidon
1-methyl-2-pyrolidone
EINECS 212-828-1
UNII-JR9CE63FPM
N-methyl-pyrrolidin-2-one
1-Methyl-2-pyrrolidinone, puriss. p.a., >=99.0% (GC)
Micropure ultra
AI3-23116
N-methylpyrolidone
N-methypyrrolidone
Max-1 peptide
Pyrol M
N-methylpirrolidone
1methylpyrrolidinone
n-methyl pyrrolidon
n-methylbutyrolactam
N-methy pyrrolidone
N-methyl-pyrolidone
N-methyl-pyrrolidon
N-methylpyrolidinone
1-methylpyrolidinone
Microposit 2001
n-methylpyrollidinone
N-Methylpyrrolidione
N-methlypyrrolidinone
N-methyl pirrolidone
N-methyl pyrollidone
N-methyl-pyrollidone
N-methylpyrrolidone-
NMP,SP Grade
1-methyl pyrrolidone
1-methyl-pyrrolidone
methyl-2-pyrrolidone
N-methy pyrrolidinone
N-methyl pyrolidinone
N-methyl-pyrolidinone
N-methyl- pyrrolidone
N-methylpyrro-lidinone
N-methylpyrroli-dinone
N-methylpyrrolidin-one
1-methyl-2pyrrolidone
1-methyl2-pyrrolidone
1methyl-2-pyrrolidone
1-methyl pyrrolidinone
1-methyl-pyrrolidinone
methylpyrrolidin-2-one
N-methy-2-pyrrolidone
N-methyl 2-pyrolidone
N-methyl-2-pyrolidone
3p1d
N-methyl 2-pyrrolidone
N-methyl-2-pyrollidone
1-methyl-2-pirrolidone
1-methyl-2-pyroldinone
1-methylpyrrolid-2-one
1methyl-2-pyrrolidinone
n-methylpyrrolidine-2one
N-methyl-2-pyrolidinone
N-methyl-2-pyrrolidinon
N-methylpyrolidin-2-one
1-methy-2-pyrrolidinone
1-methyl-2-pyrolidinone
N-methyl 2-pyrrolidinone
N-methyl-2-pyrollidinone
N-methyl-pyrrolid-2-one
N-methylpyrollidin-2-one
1 -methyl-2-pyrrolidone
1-methyl 2-pyrrolidinone
1-methyl-2-pyrollidinone
1-methyl-pyrrolin-2-one
N-Methylpyrrolidone-(2)
NMP, N-Methylpyrrolidone
1-Methyl-pyrrolidin-2one
N-methylpyrrolidine-2-one
WLN: T5NVTJ A
N-methyl -2-pyrrolidinone
1 -methyl-2-pyrrolidinone
1-methyl -2-pyrrolidinone
1-methyl-2- pyrrolidinone
EC 212-828-1
2-Pyrrolidone, 1-methyl-
1-methyl-pyrrolidine-2-one
1-N-methyl-2-pyrrolidinone
N-methyl-pyrrolidin -2-one
30207-69-3
1-Methylazacyclopentane-2-one
GTPL9520
METHYL PYRROLIDONE [II]
1-Methyl-2- pyrrolidin-2-one
1-METHYLPYRROLIDONE [MI]
METHYL PYRROLIDONE [INCI]
NSC4594
METHYLPYRROLIDONE [USP-RS]
HY-Y1275
N-METHYLPYRROLIDONE [MART.]
ZINC3860621
Tox21_202350
Tox21_300097
1-Methyl-2-pyrrolidinone, 99.5%
BDBM50353587
N-Methyl pyrrolidon (Peptide Grade)
N-METHYLPYRROLIDONE [USP-RS]
s6282
STL183295
N-Methyl-2-pyrrolidinone ACS reagent
AKOS000120930
1-Methyl-2-pyrrolidinone, BioSolv(R)
DB12521
SL 1332
1-Methyl-2-pyrrolidone, Reagent, ACS
1-METHYL-2-PYRROLIDINONE [HSDB]
NCGC00247902-01
NCGC00247902-02
NCGC00253935-01
NCGC00259899-01
BP-31156
N-METHYLPYRROLIDONE [EP MONOGRAPH]
1-Methyl-2-pyrrolidone (Low water content)
AM20110252
CS-0017258
FT-0608052
FT-0672137
FT-0698122
FT-0700571
M0418
M3055
1-Methyl-2-pyrrolidinone, analytical standard
1-Methyl-2-pyrrolidinone, anhydrous, 99.5
1-Methyl-2-pyrrolidinone, for HPLC, >=99%
1-Methyl-2-pyrrolidinone, for synthesis, 99%
D78116
M 0418
Q33103
Residual Solvent Class 2 - N-Methylpyrrolidone
1-Methyl-2-pyrrolidinone, ReagentPlus(R), 99%
1-Methyl-2-pyrrolidinone, Spectrophotometric Grade
2-PYRROLIDONE,1-METHYL MFC5 H9 N1 O1
A842053
1-Methyl-2-pyrrolidinone, ACS reagent, >=99.0%
2,5-Dichloro-4,6-dimethyl pyridine-3-carbonitrile
J-504921
J-803017
1-Methyl-2-pyrrolidinone, biotech. grade, >=99.7%
1-Methyl-2-pyrrolidinone, Electronic/Cleanroom Grade
1-Methyl-2-pyrrolidinone, p.a., ACS reagent, 99%
1-Methyl-2-pyrrolidone, anhydrous, water 40ppm max
1-Methyl-2-pyrrolidinone, SAJ first grade, >=98.0%
Z104478382
1-Methyl-2-pyrrolidinone, spectrophotometric grade, >=99%
1-Methyl-2-pyrrolidinone, Vetec(TM) reagent grade, 98%
1-Methyl-2-pyrrolidinone, for metal speciation analysis, >=99.0% (GC)
Methylpyrrolidone, United States Pharmacopeia (USP) Reference Standard
N-Methylpyrrolidone, Pharmaceutical Secondary Standard; Certified Reference Material