ethyl 3-(3-chlorophenyl)-3-oxopropanoate

• ChemBase ID: 152997
• Molecular Formular: C11H11ClO3
• Molecular Mass: 226.65624
• Monoisotopic Mass: 226.03967189
• SMILES: CCOC(=O)CC(=O)c1cccc(c1)Cl
• Canonical SMILES: CCOC(=O)CC(=O)c1cccc(c1)Cl
• InChI: InChI=1S/C11H11ClO3/c1-2-15-11(14)7-10(13)8-4-3-5-9(12)6-8/h3-6H,2,7H2,1H3
• InChIKey: WWFYJJHEBDWEJF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 3-(3-chlorophenyl)-3-oxopropanoate
• IUPAC Traditional name: ethyl 3-(3-chlorophenyl)-3-oxopropanoate
• Synonyms: ethyl 3-(3-chlorophenyl)-3-oxopropanoate; 3-Chloro-β-oxobenzenepropanoic acid ethyl ester; Ethyl 3-(3-chlorophenyl)-3-oxopropanoate; Ethyl (3-chlorobenzoyl)acetate; (3-氯苯甲酰)乙酸乙酯

Database IDs

• CAS Number: 33167-21-4
• MDL Number: MFCD03424810
• PubChem SID: 24879812; 162247138
• PubChem CID: 2757831

CALCULATED PROPERTIES

• Acid pKa: 10.5168
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.5298643
• LogD (pH = 7.4): 2.529537
• Log P: 2.5298684
• Molar Refractivity: 57.1274 cm^3
• Polarizability: 22.26122 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 257-258 °C(lit.)
• Density: 1.213 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.5460(lit.)
• Hydrophobicity(logP): 2.67

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves

Product Information

• Purity: ≥97%; 95%
• Linear Formula: ClC6H4COCH2CO2C2H5

DETAILS

Sigma Aldrich - 559288

Packaging
1, 5 g in glass bottle
Application
Reagent / reactant involved in:
• Oxidative cross-coupling via dioxygen activation with indoles1
• Chlorination and hydrosilylation for synthesis of α-hydroxy β-amino acid derivatives2
• Precursor for substrates for chiral Lewis base-catalyzed stereoselective reduction with trichlorosilane and water3
• Intramolecular cyclization for synthesis of dihydrofurans4
• Rate acceleration of Michael reactions5
• Cerium ammonium nitrate-mediated oxidative coupling6