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Succinimide

Athanor · official

C4H5NO2 · 99.09 g/mol

IUPAC name: pyrrolidine-2,5-dione

Also called butanimide, NHS core, pyrrolidine-2,5-dione

RingsReagents
Open in Athanor
The structure of Succinimide
Drawn from its SMILES with RDKit
Harmful or irritantWarningCauses skin irritation · Causes serious eye irritation · May cause respiratory irritation

Names and identifiers

IUPAC name
pyrrolidine-2,5-dione
Synonyms
butanimide, NHS core, pyrrolidine-2,5-dione
+ 37 more

2,5-Pyrrolidinedione, Butanimide, 2,5-Dioxopyrrolidine, Succinic acid imide, 2,5-Diketopyrrolidine, Succinic imide, 3,4-Dihydropyrrole-2,5-dione, Dihydro-3-pyrroline-2,5-dione, DTXSID8051629, NSC-11204, CHEBI:9307, 10X90O3503, DTXCID3030181, RefChem:6266, 204-635-6, 679-911-6, Succinimide-sauba, 3,4-Dihydropyrrolidine, MFCD00005495, NSC 11204, SUCCIMIDE, Letrozole Impurity 22, azolidine-2,5-dione, Mercury, disuccinimido-, WLN: T5VMVTJ, 2, mercury(2+) salt, Succinimide, mercury(2+) salt, EINECS 204-635-6, BRN 0108440, succinimid, cis-succinimide, AI3-08539, UNII-10X90O3503, 2,5dioxopyrrolidine, Lubrizol 6406, pyrroldine-2,5-dione, SUCCINIMIDE [MI]

Molecular formula
C4H5NO2
Empirical formula
C4H5NO2
Molecular weight
99.09 g/mol
Exact mass
99.03203
CAS number
123-56-8
PubChem CID
11439
Canonical SMILES
C1CC(=O)NC1=O
Isomeric SMILES
C1CC(=O)NC1=O
InChI
InChI=1S/C4H5NO2/c6-3-1-2-4(7)5-3/h1-2H2,(H,5,6,7)
InChIKey
KZNICNPSHKQLFF-UHFFFAOYSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms
7
Rings
1
Aromatic rings
0
Fraction sp³ carbons (Fsp3)
0.5
H-bond donors
1
H-bond acceptors
2
Rotatable bonds
0
TPSA (Ų)
46.2
Formal charge
0
XLogP3
-1 PubChem
Complexity
105 PubChem
Stereocenters
None
Double-bond geometry
None specified
Point group
C2v of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

  • C48.49%
  • H5.09%
  • N14.14%
  • O32.29%

Isotope pattern

100%99.0324.8%100.035101.037

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P
-0.58 Crippen (Wildman and Crippen 1999)
log S (water solubility)
-0.09 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
2.2 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 99.09
  • log P ≤ 5 (Crippen): -0.58
  • H-bond donors ≤ 5: 1
  • H-bond acceptors ≤ 10: 2

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

Warning

Most widely reported: 361 company reports to ECHA. Source [1].

  • Harmful or irritant
  • H315Causes skin irritation (66.5% of reports)
  • H319Causes serious eye irritation (66.5% of reports)
  • H335May cause respiratory irritation (66.5% of reports)

Precautionary statements: P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501

View all classifications (2)
  • [1] European Chemicals Agency (ECHA)This chemical does not meet GHS hazard criteria for 33.2% (120 of 361) of reports.
  • [1] European Chemicals Agency (ECHA) · 361 reports · WarningH315, H319, H335

Safety data sheets on the supplier’s page: MP Biomedicals, CymitQuimica, Thermo Fisher Scientific.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

  1. [1]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
  2. [2]NMRShiftDB · Linked only · via PubChem · retrieved 2026-10-14
  3. [3]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
  4. [4]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
  5. [5]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
  6. [6]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
  7. [7]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
  8. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  9. ·Literature on PubChem

Data last updated 2026-10-14.