Succinimide

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 450640433

| Name = Succinimide

| ImageFileL1 = Succinimide.svg

| ImageSizeL1 = 80px

| ImageAltL1 = Skeletal formula of succinimide

| ImageFileR1 = Succinimide 3D ball.png

| ImageSizeR1 = 140

| ImageAltR1 = Ball-and-stick model of the succinimide molecule

| ImageName = Succinimide

| PIN = Pyrrolidine-2,5-dione{{cite book |author=International Union of Pure and Applied Chemistry |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=The Royal Society of Chemistry |pages=869 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}

| OtherNames = Succinimide
Succinic acid imide

|Section1={{Chembox Identifiers

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 10X90O3503

| PubChem = 11439

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 10955

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 9307

| SMILES = O=C1NC(=O)CC1

| InChI = 1/C4H5NO2/c6-3-1-2-4(7)5-3/h1-2H2,(H,5,6,7)

| InChIKey = KZNICNPSHKQLFF-UHFFFAOYAV

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C4H5NO2/c6-3-1-2-4(7)5-3/h1-2H2,(H,5,6,7)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = KZNICNPSHKQLFF-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 123-56-8

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 275661

| RTECS = WN2200000

}}

|Section2={{Chembox Properties

| Properties_ref = Merck Index, 12th Edition, 9040

| C=4 | H=5 | N=1 | O=2

| Density = 1.41 g/cm³

| Appearance = White crystalline powder

| Solubility = 0.33 g/mL

| MeltingPtC = 125 to 127

| BoilingPtC = 287 to 289

| pKa = 9.5

| pKb =

| MagSus = −47.3·10⁻⁶ cm³/mol

}}

|Section6={{Chembox Pharmacology

| ATCCode_prefix = G04

| ATCCode_suffix = BX10

}}

|Section7={{Chembox Hazards

| ExternalSDS = [http://www.fishersci.com/ecomm/servlet/msdsproxy?productName=AC348650050&productDescription=succinimide--acros-organics&catNo=AC34865-0050&vendorId=VN00032119&storeId=10652 External MSDS]

| MainHazards = Irritant
Slightly Flammable

| AutoignitionPt =

| GHSPictograms =

| GHSSignalWord =

| HPhrases = {{HPhrases|}}

| PPhrases = {{PPhrases|}}

| GHS_ref = {{GESTIS|ZVG=40260 |Name=Succinimide |Date=10 December 2021}}

| LD50 = 14 g/kg (rat, oral)

}}

|Section8={{Chembox Related

| OtherFunction_label = Imides

| OtherFunction = Maleimide, N-Chlorosuccinimide, N-Bromosuccinimide

}}

}}

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.{{cite journal | doi = 10.15227/orgsyn.016.0075 | title = Succinimide | journal = Organic Syntheses | date = 1936 | volume = 16 | page = 75 }}