methyl 3-(4-chlorophenyl)-3-oxopropanoate

• ChemBase ID: 10200
• Molecular Formular: C10H9ClO3
• Molecular Mass: 212.62966
• Monoisotopic Mass: 212.02402183
• SMILES: c1c(ccc(c1)C(=O)CC(=O)OC)Cl
• Canonical SMILES: COC(=O)CC(=O)c1ccc(cc1)Cl
• InChI: InChI=1S/C10H9ClO3/c1-14-10(13)6-9(12)7-2-4-8(11)5-3-7/h2-5H,6H2,1H3
• InChIKey: OIPOJEDRCKVDJK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 3-(4-chlorophenyl)-3-oxopropanoate
• IUPAC Traditional name: methyl 3-(4-chlorophenyl)-3-oxopropanoate
• Synonyms: Methyl (4-chlorobenzoyl)acetate; Methyl 4-chlorobenzoylacetate; (p-Chlorobenzoyl)acetic acid methyl ester; Methyl 3-(4-chlorophenyl)-3-oxopropionate; Methyl (4-chlorobenzoyl)acetate; methyl 3-(4-chlorophenyl)-3-oxopropanoate; 4-氯苯甲酰乙酸甲酯

Database IDs

• CAS Number: 22027-53-8; 53101-00-1
• MDL Number: MFCD00216520
• PubChem SID: 160973507; 24881280
• PubChem CID: 735885

CALCULATED PROPERTIES

• Acid pKa: 10.841752
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.1730585
• LogD (pH = 7.4): 2.1729035
• Log P: 2.1730604
• Molar Refractivity: 52.3788 cm^3
• Polarizability: 20.434952 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~25°C; 42-46 °C(lit.); ca 25°C
• Boiling Point: 127-136°C/1.12mm; 92-98°C/0.3mm
• Flash Point: >110°C
• Hydrophobicity(logP): 2.141

Safety Information

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

Product Information

• Purity: 95%
• Empirical Formula (Hill Notation): C10H9ClO3

DETAILS

Sigma Aldrich - 590444

Packaging
5 g in glass bottle
Application
Reactant involved in:
• Oxidative coupling with aminopyridines1,2
• Enantioselective hydrogenation of unprotected β-enamine esters3
• Intramolecular cyclization4
• Oxidative alkylation of benzylic C-H bonds5
• Tandem oxidative coupling and annulation of phenols6