ethyl (2S)-5-oxopyrrolidine-2-carboxylate

• ChemBase ID: 145719
• Molecular Formular: C7H11NO3
• Molecular Mass: 157.16714
• Monoisotopic Mass: 157.07389322
• SMILES: CCOC(=O)[C@@H]1CCC(=O)N1
• Canonical SMILES: CCOC(=O)[C@@H]1CCC(=O)N1
• InChI: InChI=1S/C7H11NO3/c1-2-11-7(10)5-3-4-6(9)8-5/h5H,2-4H2,1H3,(H,8,9)/t5-/m0/s1
• InChIKey: QYJOOVQLTTVTJY-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2S)-5-oxopyrrolidine-2-carboxylate
• IUPAC Traditional name: ethyl (2S)-5-oxopyrrolidine-2-carboxylate
• Synonyms: (S)-Ethyl 5-oxopyrrolidine-2-carboxylate; 5-Oxo-L-proline Ethyl Ester; Ethyl (2S)-5-Oxopyrrolidine-2-carboxylate; Ethyl (S)-(+)-2-pyrrolidone-5-carboxylate; NSC 166529; NSC 72279; (S)-(+)-5-Ethylcarboxyl-2-pyrrolidinone; (S)-5-Oxoproline ethyl ester; L-Pyroglutamic acid ethyl ester; Ethyl (S)-(+)-2-pyrrolidone-5-carboxylate; L-Pyroglutamic acid ethyl ester; (S)-5-氧脯氨酸乙酯; L-焦谷氨酸乙酯; (S)-(+)-2-吡咯烷酮-5-羧酸乙酯; L-焦谷氨酸乙酯

Database IDs

• CAS Number: 7149-65-7
• EC Number: 230-480-9
• MDL Number: MFCD00064497
• Beilstein Number: 82621
• PubChem SID: 162239922; 24858624; 24888090
• PubChem CID: 2724446

CALCULATED PROPERTIES

• Acid pKa: 11.105785
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.38696864
• LogD (pH = 7.4): -0.38704345
• Log P: -0.3869677
• Molar Refractivity: 37.6055 cm^3
• Polarizability: 14.95568 Å^3
• Polar Surface Area: 55.4 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 47-51 °C(lit.); 54-56 °C
• Boiling Point: 176 °C/12 mmHg(lit.)
• Flash Point: 113 °C; 235.4 °F
• Optical Rotation: [α]19/D +3.3°, c = 10 in ethanol; [α]20/D +3.5±0.5°, c = 10% in ethanol

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.5% (sum of enantiomers, HPLC); 98%
• Grade: puriss.
• Optical Purity: enantiomeric ratio: ≥99:1 (GC)
• Empirical Formula (Hill Notation): C7H11NO3

DETAILS

Sigma Aldrich - 307777

Packaging
1, 5 g in glass bottle