Succinimide

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.[2]

Succinimide
Skeletal formula of succinimide
Ball-and-stick model of the succinimide molecule
Names
IUPAC name
Pyrrolidine-2,5-dione
Other names
Succinimide
Succinic acid imide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.215
RTECS number
  • WN2200000
UNII
Properties[1]
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
Main hazards Irritant
Slightly Flammable
Safety data sheet External MSDS
R/S statement (outdated) S24/25 S28 S37 S45
Lethal dose or concentration (LD, LC):
14 g/kg (rat, oral)[1]
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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Infobox references

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.

Succinimides are also used to form covalent bonds between proteins or peptides and plastics, which is useful in a variety of assay techniques.

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See also

References
  1. Merck Index, 12th Edition, 9040
  2. H. T. Clarke and Letha Davies Behr "Succinimide" Organic Syntheses 1936, volume 16, 75. doi:10.15227/orgsyn.016.0075
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