Succinimide
Skeletal formula of succinimide
Ball-and-stick model of the succinimide molecule
Names
Preferred IUPAC name
Pyrrolidine-2,5-dione[1]
Other names
Succinimide
Succinic acid imide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.215 Edit this at Wikidata
RTECS number
  • WN2200000
UNII
  • InChI=1S/C4H5NO2/c6-3-1-2-4(7)5-3/h1-2H2,(H,5,6,7) checkY
    Key: KZNICNPSHKQLFF-UHFFFAOYSA-N checkY
  • InChI=1/C4H5NO2/c6-3-1-2-4(7)5-3/h1-2H2,(H,5,6,7)
    Key: KZNICNPSHKQLFF-UHFFFAOYAV
  • O=C1NC(=O)CC1
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
 Irritant
Slightly Flammable
Lethal dose or concentration (LD, LC):
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).
☒N verify (what is checkY☒N ?)

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]

Succinimides

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.[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

References

  1. ^ 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.
  2. ^ a b Merck Index, 12th Edition, 9040
  3. ^ Record of Succinimide in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 10 December 2021.
  4. ^ H. T. Clarke and Letha Davies Behr "Succinimide" Organic Syntheses 1936, volume 16, 75. doi:10.15227/orgsyn.016.0075.
  5. ^ 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.
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