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1-Methyl-2-pyrrolidinone

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CAS:872-50-4
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1-Methyl-2-pyrrolidinone Basic information
Chemical Properties Uses
Product Name:1-Methyl-2-pyrrolidinone
Synonyms:M-PYROL(R);N-METHYLPYROLIDONE;N-METHYLPYRROLID-2-ONE;N-METHYLPYRROLIDINONE;N-METHYLPYRROLIDNONE;N-METHYLPYRROLIDONE;NMP-T;NMP-EL
CAS:872-50-4
MF:C5H9NO
MW:99.13106
EINECS:212-828-1
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Mol File:872-50-4.mol
1-Methyl-2-pyrrolidinone Structure
1-Methyl-2-pyrrolidinone Chemical Properties
Melting point −24 °C(lit.)
Boiling point 202 °C(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. 2-8°C
solubility ethanol: miscible0.1ML/mL, clear, colorless (10%, v/v)
form Liquid
color ≤20(APHA)
PH8.5-10.0 (100g/l, H2O, 20℃)
explosive limit1.3-9.5%(V)
Water Solubility >=10 g/100 mL at 20 ºC
Sensitive Hygroscopic
λmax283nm(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.
InChIKeySECXISVLQFMRJM-UHFFFAOYSA-N
CAS DataBase Reference872-50-4(CAS DataBase Reference)
NIST Chemistry Reference2-Pyrrolidinone, 1-methyl-(872-50-4)
EPA Substance Registry System2-Pyrrolidinone, 1-methyl-(872-50-4)
Safety Information
Hazard Codes T,Xi
Risk Statements 45-65-36/38-36/37/38-61-10-46
Safety Statements 41-45-53-62-26
RIDADR UN 1268 3/PG 3
WGK Germany 1
RTECS UY5790000
3-8-10
TSCA Y
Hazardous Substances Data872-50-4(Hazardous Substances Data)
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
1-Methyl-2-pyrrolidinone Usage And Synthesis
Chemical Properties1-Methyl-2-pyrrolidinone (NMP) has a molecular formula of C5H9NO, and it is a colorless to light yellow transparent liquid with a slight ammonia odor. Its boiling point is 204℃, flash point is 91℃, chroma HaZen≤25, refractive index N20D 1.468-1.471, density is 1.032-1.035. It is miscible in water at any ratio, it is soluble in ethanol, acetone, esters, halogenated hydrocarbons, aromatic hydrocarbons and other organic solvents, and it can completely mix with practically all solvents. It is strongly hygroscopic, chemically stable, not corrosive towards carbon steel and aluminum, and slightly corrosive to copper. It has low adhesiveness, strong chemical and thermal stability, high polarity, and low volatility. This product is slightly toxic, and its permitted concentration limit in air is 100PPM.
Uses
  1. 1-Methyl-2-pyrrolidinone (NMP) is a polar aprotic solvent that has the advantages of low toxicity, high boiling point, outstanding solvency, strong selectivity and good stability. It is widely used in purification of aromatic hydrocarbon extraction, acetylene, olefins, and diolefins.
  2. It is used in industrial cleaning, and it serves as a solvent for production of pesticides, engineering plastics, coatings, synthetic fibers, and integrated circuits.
  3. It can also be used as an industrial cleanser, dispersant, dye, lubricant and antifreeze.
  4. 1-Methyl-2-pyrrolidinone is an excellent solvent, widely used in aromatics extraction, lubricating oil refining, acetylene enrichment, butadiene separation and synthesis gas desulfurization.
  5. It is used in gas desulfurization, lubricating oil refining, lubricating oil antifreeze, olefin extraction, and as a solvent for insoluble engineering plastics polymerization.
  6. It 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.
  7. It is used in mediums for polymerization reactions such as engineering plastics and aramid fiber.
  8. 1-Methyl-2-pyrrolidinone is used as a polyvinylidene fluoride solvent and electrode auxiliary material for lithium ion batteries.
  9. high purity grade for ICP-MS detection.
  10. For peptide synthesis.
Chemical Propertiescolourless or light yellow liquid with an amine odour
UsesIt is a versatile industrial solvent. NMP is currently approved for use only in veterinary pharmaceuticals. The determination of the disposition and metabolism of NMP in the rat will contribute toward understanding the toxicology of this exogenous chemical which man may likely be exposed to in increasing amounts.
DefinitionChEBI: 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.
General DescriptionA 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.
Air & Water ReactionsSoluble in water.
Reactivity ProfileThis amine is a very mild chemical base. 1-Methyl-2-pyrrolidinone does tend to neutralize acids to form salts plus water. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
Health HazardInhalation of hot vapors can irritate nose and throat. Ingestion causes irritation of mouth and stomach. Contact with eyes causes irritation. Repeated and prolonged skin contact produces a mild, transient irritation.
Fire HazardSpecial Hazards of Combustion Products: Toxic oxides of nitrogen may be formed in fire.
Purification MethodsDry the pyrrolidone by removing water as the *benzene azeotrope. Fractionally distil at 10 torr through a 100-cm column packed with glass helices. [Adelman J Org Chem 29 1837 1964, McElvain & Vozza J Am Chem Soc 71 896 1949.] The hydrochloride has m 86-88o (from EtOH or Me2CO/EtOH) [Reppe et al. Justus Liebigs Ann Chem 596 1 1955]. [Beilstein 21 II 213, 21 III/IV 3145, 21/6 V 321.]
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