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Maleimide

Athanor · official

C4H3NO2 · 97.07 g/mol

IUPAC name: pyrrole-2,5-dione

Also called 1H-pyrrole-2,5-dione, thiol conjugation, bioconjugation

RingsReagents
Open in Athanor
The structure of Maleimide
Drawn from its SMILES with RDKit
CorrosiveAcute toxicityHarmful or irritantDangerToxic if swallowed · Causes severe skin burns and eye damage · May cause an allergic skin reaction

Names and identifiers

IUPAC name
pyrrole-2,5-dione
Synonyms
1H-pyrrole-2,5-dione, thiol conjugation, bioconjugation
+ 38 more

1H-Pyrrole-2,5-dione, Pyrrole-2,5-dione, 2,5-Pyrroledione, Maleic imide, DTXSID3049417, 2519R1UGP8, NSC-13684, DTXCID2029377, CHEBI:16072, RefChem:800776, 208-787-4, Maleinimide, 3-Pyrroline-2,5-dione, 2,5-dihydro-1H-pyrrole-2,5-dione, MFCD00005494, maleic acid imide, SMR000857346, CCRIS 3408, EINECS 208-787-4, NSC 13684, BRN 0106910, 5-hydroxy-2H-pyrrol-2-one, UNII-2519R1UGP8, AI3-61139, 2,5-Dioxo-2,5-dihydropyrrole; 3-Pyrroline-2,5-dione; Maleic Imide; NSC 13684;, SZB, azoline-2,5-dione, Maleimide, 99%, 5-hydroxypyrrol-2-one, WLN: T5VMVJ, SCHEMBL10990, SCHEMBL13407, 5-21-10-00003 (Beilstein Handbook Reference), cid_10935, MLS001335859, MLS001335860, SCHEMBL441985, BDBM7802

Molecular formula
C4H3NO2
Empirical formula
C4H3NO2
Molecular weight
97.07 g/mol
Exact mass
97.01638
CAS number
541-59-3
PubChem CID
10935
Canonical SMILES
C1=CC(=O)NC1=O
Isomeric SMILES
C1=CC(=O)NC1=O
InChI
InChI=1S/C4H3NO2/c6-3-1-2-4(7)5-3/h1-2H,(H,5,6,7)
InChIKey
PEEHTFAAVSWFBL-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
H-bond donors
1
H-bond acceptors
2
Rotatable bonds
0
TPSA (Ų)
46.2
Formal charge
0
XLogP3
-0.3 PubChem
Complexity
132 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

  • C49.49%
  • H3.12%
  • N14.43%
  • O32.96%

Isotope pattern

100%97.0164.8%98.01999.021

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
-0.8 Crippen (Wildman and Crippen 1999)
log S (water solubility)
0.06 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
3.11 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 97.07
  • log P ≤ 5 (Crippen): -0.8
  • 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

Danger

Most widely reported: 50 company reports to ECHA. Source [1].

  • Corrosive
  • Acute toxicity
  • Harmful or irritant
  • H301Toxic if swallowed (98% of reports)
  • H314Causes severe skin burns and eye damage
  • H317May cause an allergic skin reaction

Precautionary statements: P260, P261, P264, P270, P272, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P333+P317, P362+P364, P363, P405, P501

Safety data sheets on the supplier’s page: CymitQuimica, LGC Standards, Mcule.

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]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
  5. [5]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
  6. [6]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
  7. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  8. ·Literature on PubChem

Data last updated 2026-10-14.