2-Pyrrolidone

2-Pyrrolidone is an organic compound consisting of a 5-membered lactam, making it the simplest γ-lactam. It is a colorless liquid that is miscible with water and most common organic solvents.[3]

2-Pyrrolidone
Names
Preferred IUPAC name
Pyrrolidin-2-one
Other names
2-Pyrrolidone
2-Pyrrolidinone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.531
EC Number
  • 210-483-1
UNII
Properties
C4H7NO
Molar mass 85.106 g·mol−1
Density 1.116 g/cm3[1]
Melting point 25 °C (77 °F; 298 K)[2]
Boiling point 245 °C (473 °F; 518 K)[1]
Hazards
Safety data sheet ScienceLab.com
NFPA 704 (fire diamond)
1
2
0
Flash point 129 °C (264 °F) (open cup)[1]
138 °C (280 °F) (closed cup)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

It is produced industrially by treating butyrolactone with ammonia. Alternative routes include the partial hydrogenation of succinimide and the carbonylation of allylamine with methyl amine. 2-Pyrrolidone is an intermediate in the production of vinylpyrrolidone and the drug piracetam.[3]

Uses

A variety of pharmaceutical drugs are 2-pyrrolidone derivatives including cotinine, doxapram, piracetam, povidone, and ethosuximide.

2-Pyrrolidone is used in inkjet cartridges.[4]

Safety

2-Pyrrolidone is an eye irritant.[4]

See also

References

  1. Merck Index, 11th Edition, 8027
  2. Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. Harreus, Albrecht Ludwig; Backes, R.; Eichler, J.-O.; Feuerhake, R.; Jäkel, C.; Mahn, U.; Pinkos, R.; Vogelsang"2-Pyrrolidone, R. (2011). Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_457.pub2.
  4. "Safety Data Sheet" (PDF). HP website. HP. 7 October 2014. Retrieved 11 October 2014.
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