Succinimide

Succinimide
Names
	Preferred IUPAC name Pyrrolidine-2,5-dione
	Other names Succinimide; Succinic acid imide
Identifiers
CAS Number	123-56-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:9307 ;
ChEMBL	ChEMBL275661 ;
ChemSpider	10955 ;
ECHA InfoCard	100.004.215
PubChem CID	11439;
RTECS number	WN2200000;
UNII	10X90O3503 ;
CompTox Dashboard (EPA)	DTXSID8051629 ;
	InChI InChI=1S/C4H5NO2/c6-3-1-2-4(7)5-3/h1-2H2,(H,5,6,7) Key: KZNICNPSHKQLFF-UHFFFAOYSA-N ; 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
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)
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). verify (what is ?) 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.^[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.

References

^ 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.
^ H. T. Clarke and Letha Davies Behr "Succinimide" Organic Syntheses 1936, volume 16, 75. 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.

[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.

[Merck-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.

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Succinimides

See also

References