Succinimide
Succinimide
Chemical compound
Succinimide is an organic compound with the formula (CH2)2(CO)2NH. This white solid is used in a variety of organic syntheses, as well as in some industrial silver plating processes. The compound is classified as a cyclic imide. It may be prepared by thermal decomposition of ammonium succinate.[3]
Quick Facts Names, Identifiers ...
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| Names | |||
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| Preferred IUPAC name
Pyrrolidine-2,5-dione[1] | |||
| Other names
Succinimide Succinic acid imide | |||
| Identifiers | |||
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| ECHA InfoCard | 100.004.215  | ||
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| Properties[2] | |||
| C4H5NO2 | |||
| Molar mass | 99.089 g·mol−1 | ||
| Appearance | White crystalline powder | ||
| Density | 1.41 g/cm3 | ||
| Melting point | 125 to 127 °C (257 to 261 °F; 398 to 400 K) | ||
| Boiling point | 287 to 289 °C (549 to 552 °F; 560 to 562 K) | ||
| 0.33 g/mL | |||
| Acidity (pKa) | 9.5 | ||
| -47.3·10−6 cm3/mol | |||
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| G04BX10 (WHO) | |||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards |
Irritant Slightly Flammable | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) |
14 g/kg (rat, oral)[2] | ||
| Safety data sheet (SDS) | External MSDS | ||
| Related compounds | |||
Related Imides |
Maleimide, N-Chlorosuccinimide, N-Bromosuccinimide | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Succinimides refers to compounds that contain the succinimide group. These compounds have some notable uses. Several succinimides are used as anticonvulsant drugs, including ethosuximide, phensuximide, and methsuximide.[4]
Succinimides are also used to form covalent bonds between proteins or peptides and plastics, which is useful in a variety of assay techniques.
- International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 869. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
- Merck Index, 12th Edition, 9040
- H. T. Clarke and Letha Davies Behr "Succinimide" Organic Syntheses 1936, volume 16, 75. doi:10.15227/orgsyn.016.0075.