(4S)-3-[(benzyloxy)carbonyl]-2-oxoimidazolidine-4-carboxylic acid

• ChemBase ID: 59393
• Molecular Formular: C12H12N2O5
• Molecular Mass: 264.23408
• Monoisotopic Mass: 264.07462149
• SMILES: N1([C@@H](CNC1=O)C(=O)O)C(=O)OCc1ccccc1
• Canonical SMILES: O=C(N1C(=O)NC[C@H]1C(=O)O)OCc1ccccc1
• InChI: InChI=1S/C12H12N2O5/c15-10(16)9-6-13-11(17)14(9)12(18)19-7-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,13,17)(H,15,16)/t9-/m0/s1
• InChIKey: AYSUEIZKNBGWGN-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-3-[(benzyloxy)carbonyl]-2-oxoimidazolidine-4-carboxylic acid
• IUPAC Traditional name: (4S)-3-[(benzyloxy)carbonyl]-2-oxoimidazolidine-4-carboxylic acid
• Synonyms: (S)-(-)-2-Oxo-1,5-imidazolidinedicarboxylic acid 1-benzyl ester; (S)-(-)-1-Z-2-Oxo-5-imidazolidinecarboxylic acid; (4S)-3-[(Benzyloxy)carbonyl]-2-oxoimidazolidine-4-carboxylic acid; (S)-(-)-2-氧代-1,5-咪唑烷二羧酸 1-苄酯; (S)-(-)-1-Z-2-氧-5-咪唑烷羧酸

Database IDs

• CAS Number: 59760-01-9
• MDL Number: MFCD00192373
• PubChem SID: 162064156; 24864442
• PubChem CID: 688196

CALCULATED PROPERTIES

• Acid pKa: 3.468491
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.08764
• LogD (pH = 7.4): -2.4502532
• Log P: 0.9343055
• Molar Refractivity: 62.599 cm^3
• Polarizability: 24.420984 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 189 °C (dec.)(lit.)
• Optical Rotation: [α]24/D -63.0°, c = 2.5 in methanol

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false
• 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%
• Empirical Formula (Hill Notation): C12H12N2O5

DETAILS

Sigma Aldrich - 392308

Packaging
5 g in glass bottle
Application
Z-protected imidazolidinone for sequential N-alkylation.1