N-Methylsuccinimide
From Wikipedia, the free encyclopedia
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| Names | |
|---|---|
| IUPAC name
1-Methylpyrrolidine-2,5-dione | |
| Systematic IUPAC name
1-Methyl-2,5-pyrrolidinedione | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| Abbreviations | MSI |
| 110486 | |
| ChEMBL | |
| ChemSpider | |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C5H7NO2 | |
| Molar mass | 113.116 g·mol−1 |
| Appearance | White to off-white crystalline powder |
| Density | 1.127 g/mL |
| Melting point | 66 to 69 °C (151 to 156 °F; 339 to 342 K) (also reported as 68–71 °C and 66–67 °C) |
| Boiling point | 235 °C (455 °F; 508 K) (also reported as 234–235 °C) |
| Soluble in water | |
| Vapor pressure | 0.0±0.5 mmHg at 25 °C (Predicted) |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
Irritant |
| GHS labelling: | |
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| Warning | |
| H315, H319, H335 | |
| P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
| Flash point | 142.1(Predicted) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N-Methylsuccinimide (also known as 1-methyl-2,5-pyrrolidinedione, abbreviated MSI) is an organic compound chemically related to succinimide. It is primarily characterized as a major metabolic product of the industrial solvent N-methyl-2-pyrrolidone (NMP) in mammals, including humans and rats.
One patent describes the reaction of aqueous ammonia and succinate with a methylating agent at temperatures ranging from 100 °C to 400 °C. The resulting N-methylsuccinimide can subsequently be purified and hydrogenated to form NMP.[1] It can also be produced by the reaction of diammonium succinate with methanol or by the reaction of succinic anhydride with methylamine.[2]
In the microelectronics industry, the oxidative degradation of NMP during fabrication processes results in the formation of N-methylsuccinimide.[3] Consequently, it is found in waste NMP mixed liquors. Patents describe methods for purifying waste NMP by removing impurities such as N-methylsuccinimide and gamma-butyrolactone (GBL) using alkali treatment to recover high-purity NMP.[4]