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.[4]
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| Names | |||
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| Preferred IUPAC name
Pyrrolidine-2,5-dione[1] | |||
| Other names
Succinimide
Succinic acid imide | |||
| Identifiers | |||
3D model (JSmol)
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| ChEMBL | |||
| ChemSpider | |||
| ECHA InfoCard | 100.004.215 | ||
PubChem CID
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CompTox Dashboard (EPA)
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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 | |||
| Pharmacology | |||
| G04BX10 (WHO) | |||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards
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Irritant Slightly Flammable | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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14 g/kg (rat, oral)[2] | ||
| Safety data sheet (SDS) | External MSDS | ||
| Related compounds | |||
Related Imides
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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
editSuccinimides 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.[5]
Succinimides are also used to form covalent bonds between proteins or peptides and plastics, which is useful in a variety of assay techniques.
See also
editReferences
edit- ^ 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.
- ^ a b Merck Index, 12th Edition, 9040
- ^ Record of Succinimide in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 10 December 2021.
- ^ "Succinimide". Organic Syntheses. 16: 75. 1936. doi:10.15227/orgsyn.016.0075.
- ^ Zhao, Zefeng; Yue, Jiangxin; Ji, Xiaotong; Nian, Meng; Kang, Kaiwen; Qiao, Haifa; Zheng, Xiaohui (2021). "Research progress in biological activities of succinimide derivatives". Bioorganic Chemistry. 108: 104557. doi:10.1016/j.bioorg.2020.104557. PMID 33376010. S2CID 229722680.