(5S)-5-(hydroxymethyl)pyrrolidin-2-one

• ChemBase ID: 67322
• Molecular Formular: C5H9NO2
• Molecular Mass: 115.13046
• Monoisotopic Mass: 115.06332853
• SMILES: N1C(=O)CC[C@H]1CO
• Canonical SMILES: OC[C@@H]1CCC(=O)N1
• InChI: InChI=1S/C5H9NO2/c7-3-4-1-2-5(8)6-4/h4,7H,1-3H2,(H,6,8)/t4-/m0/s1
• InChIKey: HOBJEFOCIRXQKH-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S)-5-(hydroxymethyl)pyrrolidin-2-one
• IUPAC Traditional name: (5S)-5-(hydroxymethyl)pyrrolidin-2-one
• Synonyms: (S)-(+)-5-Hydroxymethyl-2-pyrrolidinone; (S)-5-(Hydroxymethyl)-2-pyrrolidone; (S)-2-(Hydroxymethyl)pyrrolidin-5-one; (+)-5-(Hydroxymethyl)-2-pyrrolidinone; (S)-Pyroglutaminol; L-Pyroglutaminol; (S)-5-(Hydroxymethyl)-2-pyrrolidinone; (S)-5-(Hydroxymethyl)-2-pyrrolidinone; H-Pyr-ol; (S)-(+)-5-(Hydroxymethyl)-2-pyrrolidinone; (5S)-5-(hydroxymethyl)pyrrolidin-2-one; L-焦谷氨醇; (S)-5-(羟甲基)-2-吡咯烷酮; L-焦谷氨醇; (S)-(+)-5-羟甲基-2-吡咯烷

Database IDs

• CAS Number: 17342-08-4
• MDL Number: MFCD00077792
• Beilstein Number: 80670; 4657914
• PubChem SID: 162033058; 24862646
• PubChem CID: 643511

CALCULATED PROPERTIES

• Acid pKa: 14.226303
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -1.2099442
• LogD (pH = 7.4): -1.2099442
• Log P: -1.2099442
• Molar Refractivity: 28.2204 cm^3
• Polarizability: 11.098675 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: White Solid; 白色结晶粉末
• Melting Point: 72-73°C; 72-74°C; 78-82°C; 79-80 °C(lit.); 79-85 °C; 83 - 85°C
• Boiling Point: 147-149°C/0.06m
• Optical Rotation: [α]/D +30.5±2.0°, c = 5 in ethanol; [α]20/D +30°, c = 2 in ethanol; +30 (c=2 in ethanol); +31°(c = 2% in EtOH)
• Hydrophobicity(logP): -1.475

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99.0% (sum of enantiomers, HPLC); 95%; 95+%; 97%; 98%
• Grade: puriss.
• Empirical Formula (Hill Notation): C5H9NO2

DETAILS

Sigma Aldrich - 366366

Packaging
5 g in glass bottle
Application
Serves as a building block in the synthesis of (R)- and (S)-diaminovaleric acids1 and of 5-azasemicorrin bidentate nitrogen ligands for enantioselective catalysis.2