ethyl 2-fluoro-3-oxobutanoate

• ChemBase ID: 8595
• Molecular Formular: C6H9FO3
• Molecular Mass: 148.1322632
• Monoisotopic Mass: 148.05357237
• SMILES: O=C(C(C(=O)C)F)OCC
• Canonical SMILES: CCOC(=O)C(C(=O)C)F
• InChI: InChI=1S/C6H9FO3/c1-3-10-6(9)5(7)4(2)8/h5H,3H2,1-2H3
• InChIKey: SHTFQLHOTAJQRJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-fluoro-3-oxobutanoate
• IUPAC Traditional name: ethyl 2-fluoro-3-oxobutanoate
• Synonyms: 2-Fluoro-3-oxobutanoic acid ethyl ester; Ethyl 2-fluoro-3-oxobutanoate; Ethyl 2-fluoro-3-oxobutyrate; NSC 24563; Ethyl 2-fluoroacetoacetate; Ethyl 2-fluoroacetoacetate; 2-氟乙酰乙酸乙酯

Database IDs

• CAS Number: 1522-41-4
• MDL Number: MFCD00215830
• PubChem SID: 160971902; 24873190
• PubChem CID: 230078

CALCULATED PROPERTIES

• Acid pKa: 8.694438
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.9101997
• LogD (pH = 7.4): 0.88899094
• Log P: 0.6771436
• Molar Refractivity: 31.7027 cm^3
• Polarizability: 12.5239 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 183 °C(lit.); 183°C
• Flash Point: 194 °F; 90 °C; 90°C
• Density: 1.181; 1.181 g/mL at 25 °C(lit.)
• Refractive Index: 1.414; n20/D 1.414(lit.)

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: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Linear Formula: CH3COCH(F)CO2C2H5

DETAILS

Sigma Aldrich - 498327

Packaging
25 mL in glass bottle
Application
Reactant for:
• Michael addition-induced cyclization reaction1
• Asymmetric Mannich reaction2
• Enantioselective organocatalytic conjugate addition3