Succinimide

Succinimide

Names
Preferred IUPAC name Pyrrolidine-2,5-dione [1]
Other names Succinimide Succinic acid imide
Identifiers
CAS Number	123-56-8  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:9307  N
ChEMBL	ChEMBL275661  Y
ChemSpider	10955  Y
ECHA InfoCard	100.004.215
PubChem CID	11439
RTECS number	WN2200000
UNII	10X90O3503  Y
CompTox Dashboard (EPA)	DTXSID8051629
InChI InChI=1S/C4H5NO2/c6-3-1-2-4(7)5-3/h1-2H2,(H,5,6,7) Y Key: KZNICNPSHKQLFF-UHFFFAOYSA-N Y InChI=1/C4H5NO2/c6-3-1-2-4(7)5-3/h1-2H2,(H,5,6,7) Key: KZNICNPSHKQLFF-UHFFFAOYAV
SMILES O=C1NC(=O)CC1
Properties [2]
Chemical formula	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)
Solubility in water	0.33 g/mL
Acidity (pKa)	9.5
Magnetic susceptibility (χ)	-47.3·10−6 cm3/mol
Pharmacology
ATC code	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). N  verify  (what is  YN ?) Infobox references

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]

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. ^[4]

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

• Succinic anhydride
• N-Hydroxysuccinimide
• N-Bromosuccinimide

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. Merck Index , 12th Edition, 9040
3. "Succinimide". Organic Syntheses. 16: 75. 1936. doi:10.15227/orgsyn.016.0075.
4. 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.