(4S)-4-hydroxypyrrolidin-2-one

• ChemBase ID: 68902
• Molecular Formular: C4H7NO2
• Molecular Mass: 101.10388
• Monoisotopic Mass: 101.04767847
• SMILES: N1C(=O)C[C@@H](C1)O
• Canonical SMILES: O[C@H]1CC(=O)NC1
• InChI: InChI=1S/C4H7NO2/c6-3-1-4(7)5-2-3/h3,6H,1-2H2,(H,5,7)/t3-/m0/s1
• InChIKey: IOGISYQVOGVIEU-VKHMYHEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-hydroxypyrrolidin-2-one
• IUPAC Traditional name: (4S)-4-hydroxypyrrolidin-2-one
• Synonyms: (S)-β-Hydroxy-γ-butyrolactam; (S)-(-)-4-Hydroxy-2-pyrrolidinone; (4S)-(-)-4-Hydroxy-2-oxopyrrolidine; (4S)-(-)-beta-Hydroxy-gamma-butyrolactam; (4S)-(-)-4-Hydroxypyrrolidin-2-one; (S)-4-Hydroxy-2-pyrrolidinone; (4S)-4-Hydroxy-2-pyrrolidinone; (S)-(-)-4-Hydroxy-2-pyrrolidinone; (S)-4-Hydroxy-2-pyrrolidone; (S)-(-)-4-Hydroxy-2-pyrrolidinone; (S)-4-Hydroxypyrrolidine-2-one; (S)-(-)-β-Hydroxy-γ-butyrolactam; (S)-4-Hydroxy-2-pyrrolidone; (S)-β-羟基-γ-丁内酰胺; (S)-(-)-4-羟基-2-吡咯烷酮; (S)-(-)-β-羟基-γ-丁内酰胺; (S)-4-羟基-2-吡咯酮

Database IDs

• CAS Number: 68108-18-9
• MDL Number: MFCD00273370
• Beilstein Number: 1524192
• PubChem SID: 162034632; 24887015; 24871604
• PubChem CID: 155084

CALCULATED PROPERTIES

• Acid pKa: 14.054872
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -1.4986055
• LogD (pH = 7.4): -1.4986055
• Log P: -1.4986055
• Molar Refractivity: 23.4654 cm^3
• Polarizability: 9.2818985 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 156-159 °C(lit.); 156-159°C; 156-160 °C
• Optical Rotation: [α]20/D -41±3°, c = 1% in ethanol; [α]23/D -43°, c = 1 in ethanol

Safety Information

• Storage Warning: Harmful/Irritant/Keep Cold; IRRITANT
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-41
• Safety Statements: 26-36
• TSCA Listed: false
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97.0% (sum of enantiomers, GC); 95+%; 97%
• Grade: purum
• Empirical Formula (Hill Notation): C4H7NO2

DETAILS

Sigma Aldrich - 479179

Packaging
1, 5 g in glass bottle

Toronto Research Chemicals - H953075

The (S)-enantiomer intermediate in the preparation of Oxiracetam

REFERENCES

• Kondepudi, D., et al.: Science, 250 975 (1990), Di Silvestro, G., et al.: J. Pharm. Sci., 82, 758 (1993),