1-Methyl-2-pyrrolidinone
[CAS# 872-50-4]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: 1-Methyl-2-pyrrolidinone
• Synonyms: N-Methyl-2-pyrrolidinone; N-Methyl-2-Pyrrolidone; N-Methylpyrrolidone; NMP
• Molecular Formula: C₅H₉NO
• Molecular Weight: 99.13
• CAS Registry Number: 872-50-4
• EC Number: 212-828-1
• SMILES: CN1CCCC1=O

Properties

• Density: 1.033
• Melting point: -24 ºC
• Boiling point: 202 ºC
• Flash point: 91 ºC
• Water solubility: >=10 g/100 mL at 20 ºC

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Hazard Statements: H315-H319-H335-H360
• Precautionary Statements: P203-P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P318-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Reproductive toxicity	Repr.	1B	H360
Reproductive toxicity	Repr.	1B	H360D
Specific target organ toxicity - single exposure	STOT SE	3	H370
Reproductive toxicity	Repr.	1A	H360
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2A	H319
Reproductive toxicity	Repr.	2	H361
Acute toxicity	Acute Tox.	4	H332
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Specific target organ toxicity - single exposure	STOT SE	3	H336
Aspiration hazard	Asp. Tox.	1	H304
Reproductive toxicity	Repr.	1B	H360D

Discovory and Applicatios

1-Methyl-2-pyrrolidone (NMP), with the chemical formula C₅H₉NO, is a versatile compound known for its unique solvent properties and applications in various industries. It belongs to the class of pyrrolidones, which are characterized by a five-membered ring structure containing nitrogen. 1-Methyl-2-pyrrolidone was first synthesized and characterized in the mid-20th century as part of organic chemistry research aimed at developing efficient solvents with a variety of industrial applications. Its discovery stemmed from the exploration of pyrrolidone derivatives and their potential as high-boiling point solvents capable of dissolving a wide range of organic and inorganic substances.

The synthesis of 1-methyl-2-pyrrolidone generally involves the reaction of gamma-butyrolactone with methylamine under controlled conditions to form 1-methyl-2-pyrrolidone as the major product. The crude product undergoes a purification process to remove impurities and obtain a high purity suitable for industrial applications.

1-Methyl-2-pyrrolidone is widely used as a high-boiling point solvent in various industrial processes, including petrochemicals, pharmaceuticals, electronics, and polymers. Its ability to dissolve a wide range of substances makes it useful in formulations and chemical reactions where other solvents may not be effective.

In the polymer industry, NMP is used as a solvent for polymer dissolution, spinning, and casting processes. It is particularly useful in the production of polyvinylidene fluoride (PVDF) and other specialty polymers, helping to maintain polymer viscosity and processing efficiency.

NMP is used in electronics manufacturing to clean and degrease semiconductor materials and electronic components. Its high solvency and low toxicity make it suitable for removing photoresists and other contaminants without damaging sensitive electronic devices.

In the pharmaceutical industry, 1-methyl-2-pyrrolidone is used as a solvent for drug formulations and active pharmaceutical ingredients (APIs). It helps dissolve poorly soluble drugs and improves the bioavailability of drug formulations.

Although 1-methyl-2-pyrrolidone is relatively safe when handled correctly, precautions should be taken to minimize exposure. It is important to use NMP in well-ventilated areas or under controlled laboratory conditions to prevent inhalation or skin contact. Safety guidelines recommend the use of personal protective equipment (PPE), such as gloves and goggles, when handling this solvent.

References

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DOI: 10.1016/j.ejpb.2010.07.009

2008. Solubility of Small-Molecule Crystals in Polymers: d-Mannitol in PVP, Indomethacin in PVP/VA, and Nifedipine in PVP/VA. Pharmaceutical Research, 25(12).
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