Succinimide

Last updated
Succinimide
Succinimide.svg
Succinimide 3D ball.png
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
RTECS number
  • WN2200000
UNII
  • InChI=1S/C4H5NO2/c6-3-1-2-4(7)5-3/h1-2H2,(H,5,6,7) Yes check.svgY
    Key: KZNICNPSHKQLFF-UHFFFAOYSA-N Yes check.svgY
  • 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
AppearanceWhite 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
GHS labelling: [3]
[ ? ]
[ ? ]
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Contents

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

Related Research Articles

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<i>N</i>-Bromosuccinimide Molecule

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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. 1 2 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.