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(Top) 1 Succinimides 2 See also 3 References

Succinimide

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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 (pK_a)

9.5

Magnetic susceptibility (χ)

-47.3·10⁻⁶cm³/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

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 decompositionofammonium succinate.^[4]

Succinimides

[edit]

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 proteinsorpeptides and plastics, which is useful in a variety of assay techniques.

References

[edit]

^ 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.