2,5-dihydro-1H-pyrrole-2,5-dione

• ChemBase ID: 89859
• Molecular Formular: C4H3NO2
• Molecular Mass: 97.07212
• Monoisotopic Mass: 97.01637834
• SMILES: N1C(=O)C=CC1=O
• Canonical SMILES: O=C1C=CC(=O)N1
• InChI: InChI=1S/C4H3NO2/c6-3-1-2-4(7)5-3/h1-2H,(H,5,6,7)
• InChIKey: PEEHTFAAVSWFBL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dihydro-1H-pyrrole-2,5-dione
• IUPAC Traditional name: maleimide
• Synonyms: 2,5-dihydro-1H-pyrrole-2,5-dione; 2,5-Dioxo-2,5-dihydropyrrole; 3-Pyrroline-2,5-dione; Maleic Imide; NSC 13684; Maleimide; 1H-Pyrrole-2,5-dione; 2,5-Dihydro-2,5-dioxo-1H-pyrrole; Maleimide; 2,5-Pyrroledione; 2,5-Dioxo-3-pyrroline; 2,5-吡咯二酮; 马来酰亚胺

Database IDs

• CAS Number: 541-59-3
• EC Number: 208-787-4
• MDL Number: MFCD00005494
• Beilstein Number: 106910
• PubChem SID: 24847914; 162076714; 24882436
• PubChem CID: 10935
• CHEBI ID: 16072
• CHEMBL: 387762
• Chemspider ID: 10471
• Wikipedia Title: Maleimide

CALCULATED PROPERTIES

• Acid pKa: 10.040194
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.6359153
• LogD (pH = 7.4): -0.6368849
• Log P: -0.63590294
• Molar Refractivity: 23.3514 cm^3
• Polarizability: 8.497091 Å^3
• Polar Surface Area: 46.17 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; organic solvents; Soluble in water
• Apperance: White Solid
• Melting Point: 80-84°C; 90-94°C; 91 - 93°C; 91-93 °C; 91-93 °C(lit.); 91-93°C
• Boiling Point: 97-103°C/5mm; 97-103/5mm
• Density: 1.249
• Hydrophobicity(logP): -0.306

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Corrosive/Toxic/Harmful/Lachrymatory
• RTECS: ON4800000
• European Hazard Symbols: Toxic (T)
• UN Number: 2923; UN2923
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; III
• Risk Statements: 25-34-43; R25 R34 R43
• Safety Statements: 20-26-36/37/39-45; 26-36/37/39-45; S26 S36/37/39 S45
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H314-H317; H301-H317-H314-H318
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A; P280-P301 + P310-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2923 8/PG 2

Product Information

• Purity: ≥98.0% (HPLC); 95%; 98+%; 99%
• Grade: purum
• Empirical Formula (Hill Notation): C4H3NO2

DETAILS

Sigma Aldrich - 129585

Application
Rhodium-catalyzed conjugate arylation with arylboronic acids.1
Packaging
10, 25 g in poly bottle
2 g in glass bottle

REFERENCES

• Stereoselective Diels-Alder reaction with an exocyclic diene has been used in the synthesis of a cyclohexannulated [5.3.1]propellane as a precursor of an ABC ring analogue of paclitaxel (Taxol): J. Chem. Soc., Chem. Commun., 1395 (1995).