benzyl 4-oxopiperidine-1-carboxylate

• ChemBase ID: 66673
• Molecular Formular: C13H15NO3
• Molecular Mass: 233.2631
• Monoisotopic Mass: 233.10519335
• SMILES: N1(CCC(=O)CC1)C(=O)OCc1ccccc1
• Canonical SMILES: O=C(N1CCC(=O)CC1)OCc1ccccc1
• InChI: InChI=1S/C13H15NO3/c15-12-6-8-14(9-7-12)13(16)17-10-11-4-2-1-3-5-11/h1-5H,6-10H2
• InChIKey: VZOVOHRDLOYBJX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl 4-oxopiperidine-1-carboxylate
• IUPAC Traditional name: benzyl 4-oxopiperidine-1-carboxylate
• Synonyms: N-(Benzyloxycarbonyl)piperidin-4-one; Piperidin-4-one, N-CBZ protected; Benzyl 4-Oxo-1-Piperidinecarboxylate; 4-Oxopiperidine-1-carboxylic Acid Benzyl Ester; 1-Benzyloxycarbonyl-4-oxopiperidine; 1-Carbobenzoxy-4-piperidone; N-(Benzyloxycarbonyl)-4-piperidone; 1-Cbz-piperidin-4-one; 1-(Benzyloxycarbonyl)-4-piperidinone; 1-Cbz-4-Piperidone; Benzyl 4-oxo-1-piperidinecarboxylate; 1-Z-4-Piperidone; N-Cbz-4-piperidone; 1-Benzyloxycarbonyl-4-piperidone; benzyl 4-oxopiperidine-1-carboxylate; N-BENZYLOXYCARBONYL-4-PIPERIDONE; 1-苄氧羰基-4-哌啶酮; N-CBZ-4-哌啶酮; N-苄氧羰基-4-哌啶酮; 1-Cbz-4-哌啶酮; N-苄氧羰基--4-哌啶酮

Database IDs

• CAS Number: 19099-93-5
• MDL Number: MFCD00673144
• Beilstein Number: 1533716
• PubChem SID: 162032410; 24870202
• PubChem CID: 643496

CALCULATED PROPERTIES

• Acid pKa: 18.640947
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.7437913
• LogD (pH = 7.4): 1.7437913
• Log P: 1.7437913
• Molar Refractivity: 62.9709 cm^3
• Polarizability: 24.470201 Å^3
• Polar Surface Area: 46.61 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Colourless Oil
• Melting Point: 38-41°C; 38-47°C
• Boiling Point: 114-140 °C/0.25 mmHg(lit.); 114-140°C/0.24mm
• Flash Point: >110°C(230°F); 113 °C; 113°C; 235.4 °F
• Density: 1.172; 1.172 g/mL at 25 °C(lit.)
• Refractive Index: 1.542; n20/D 1.542; n20/D 1.542(lit.)
• Hydrophobicity(logP): 2.442

Safety Information

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

Product Information

• Purity: ≥95.0% (HPLC); 95%; 95+%; 98%; 98+%; 99%
• Grade: purum
• Empirical Formula (Hill Notation): C13H15NO3

DETAILS

Sigma Aldrich - 464643

Application
Protected piperidinone that can undergo interesting synthetic transformations including the Knoevenagel reaction,1 hetero-Diels-Alder reactions,2 and reactions to form N-(4-piperidinyl)oxindoles.3
Starting material in a synthesis of a GABA analogue by direct Barbier-like addition of an alkyl phosphinate.
Packaging
5, 25, 100 mL in glass bottle