ethyl 4-chloro-3-oxobutanoate

• ChemBase ID: 85727
• Molecular Formular: C6H9ClO3
• Molecular Mass: 164.58686
• Monoisotopic Mass: 164.02402183
• SMILES: O=C(CC(=O)CCl)OCC
• Canonical SMILES: CCOC(=O)CC(=O)CCl
• InChI: InChI=1S/C6H9ClO3/c1-2-10-6(9)3-5(8)4-7/h2-4H2,1H3
• InChIKey: OHLRLMWUFVDREV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 4-chloro-3-oxobutanoate
• IUPAC Traditional name: ethyl 4-chloro-3-oxobutanoate
• Synonyms: 4-Chloro-3-oxobutanoic Acid Ethyl Ester; Ethyl 3-Oxo-4-chlorobutanoate; Ethyl γ-Chloroacetoacetate; Ethyl ω-Chloroacetoacetate; γ-Chloroacetoacetic Acid Ethyl Ester; ethyl 4-chloro-3-oxobutanoate; Ethyl 4-chloroacetoacetate; Ethyl 4-chloro-3-oxobutanoate; Ethyl 4-chloroacetoacetate; 4-Chloroacetoacetic acid ethyl ester; 4-氯乙酰乙酸乙酯

Database IDs

• CAS Number: 638-07-3
• EC Number: 211-317-0
• MDL Number: MFCD00000939
• Beilstein Number: 1761275
• PubChem SID: 24850895; 162072843; 24853676
• PubChem CID: 69484

CALCULATED PROPERTIES

• Acid pKa: 9.120907
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.2717835
• LogD (pH = 7.4): 1.2637123
• Log P: 1.0385541
• Molar Refractivity: 36.8098 cm^3
• Polarizability: 14.591225 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Clear Colorless Liquid
• Melting Point: -8°C
• Boiling Point: 115 °C/14 mmHg(lit.); 115°C/14mm; 220°C
• Flash Point: 105 °C; 105°C; 221 °F; 92°C(198°F)
• Density: 1.212; 1.218; 1.218 g/mL at 25 °C(lit.)
• Refractive Index: 1.452; 1.4520; n20/D 1.452; n20/D 1.452(lit.)

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Toxic/Corrosive/Lachrymatory/Store under Argon
• RTECS: AK5110000
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 2922; UN2922
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 25-34; 25-34-51/53
• Safety Statements: 26-36/37/39-45-57; 26-36-45
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H314; H301-H314-H318-H227-H401-H411
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A; P280-P301 + P310-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2922 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (GC); ≥97.0% (GC); 95%; 97%
• Grade: Lonza quality; purum
• Impurities: ≤0.04% metyl-4-chloroacetoacetate
• Linear Formula: ClCH2COCH2CO2C2H5

DETAILS

Sigma Aldrich - 180769

Packaging
50, 250 g in glass bottle

Sigma Aldrich - 690295

Packaging
1 kg in poly bottle
25 kg in comp drum

REFERENCES

• Isothiocyanates similarly give 2-aminothiophenones: J. Chem. Soc., Perkin 1, 1078 (1981).
• Reacts at the 2-position with isocyanates in the presence of base to give 2-aminofuranone derivatives via a ketene N-acetal intermediate: Chem. Ber., 109, 212 (1976):
  
• Acid-catalyzed reaction with phenols gives 3-(chloromethyl)coumarins, readily convertible to benzofuran-3-acetic acids: Heterocycles, 41, 647 (1995):