ethyl 3-oxobutanoate

• ChemBase ID: 102058
• Molecular Formular: C6H10O3
• Molecular Mass: 130.1418
• Monoisotopic Mass: 130.06299418
• SMILES: CCOC(=O)CC(=O)C
• Canonical SMILES: CCOC(=O)CC(=O)C
• InChI: InChI=1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3
• InChIKey: XYIBRDXRRQCHLP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 3-oxobutanoate
• IUPAC Traditional name: ethyl acetoacetate
• Synonyms: EAA; ethyl 3-oxobutanoate; Ethyl acetoacetate; Ethyl Acetoacetate; Acetoacetic ester; ACETOACETIC ACID ETHYL ESTER; Acetoacetic acid ethyl ester; Ethyl acetylacetate; 3-Oxobutanoic acid ethyl ester; Ethyl acetoacetate; ACE; 乙酰醋酸乙酯; 乙酰乙酸乙酯

Database IDs

• CAS Number: 141-97-9
• EC Number: 205-516-1
• MDL Number: MFCD00009199
• Beilstein Number: 385838
• Merck Index: 143758
• PubChem SID: 24878213; 24846884; 24901056; 162088364; 24845029; 24901055; 24845025
• PubChem CID: 8868
• CHEMBL: 169176
• Chemspider ID: 13865426
• FEMA ID: 2415
• KEGG ID: C03500
• Unique Ingredient Identifier: IZP61H3TB1
• Wikipedia Title: Ethyl_acetoacetate
• Council of Europe Number: 240; 240c
• Flavis Number: 9.402

CALCULATED PROPERTIES

• Acid pKa: 9.93099
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.7345275
• LogD (pH = 7.4): 0.73326755
• Log P: 0.5012103
• Molar Refractivity: 32.0566 cm^3
• Polarizability: 12.67607 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 2.86 g/100 ml (20 °C) in water
• Apperance: APHA: ≤15; Colourless liquid; with fruit or rum odour
• Melting Point: -39 - -44 °C; -43 °C(lit.); -43°C; -45 °C (228 K)
• Boiling Point: 178 - 187 °C at 1013 hPa; 180 °C; 180.8 °C (454.0 K); 180-181°C; 181 °C(lit.)
• Flash Point: 185 °F; 70 °C; 84.4°C; 84°C(183°F); 85 °C
• Auto Ignition Point: 280 °C; 580 °F
• Density: 1.021 g/cm^3, liquid; 1.025; 1.027 - 1.03 g/cm^3 at 20 °C; 1.029 g/mL at 20 °C(lit.)
• Refractive Index: 1.4190; n20/D 1.419
• Vapor Pressure: 1 hPa at 20 °C; 1 mmHg ( 28.5 °C)
• Vapor Density: 4.48 (vs air); 4.49 (air = 1)
• pKa: 10.68 (in H₂O); 14.2 (in DMSO)
• Organoleptic: ethereal; sweet; fruity; ethereal

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: AK5250000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 36; R:36/37/38
• Safety Statements: 26; 26-60; S:20-25-26-37/39
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• NFPA704:
  

  2

  2
• Explode Limits: 9.5 %
• GHS Hazard statements: H319; H319-H227-H303
• GHS Precautionary statements: P210-P280-P305+P351+P338-P312-P403+P235-P501A; P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Regulation Compliance: EU Regulation 1334/2008 & 178/2002; FCC; FDA 21 CFR (172.515); FDA 21 CFR (175.300)

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥98.0% (GC); ≥99%; ≥99.0% (GC); 99%; 99+%
• Grade: FG; Halal; Kosher; Lonza quality; natural; NI; produced by Wacker; puriss. p.a.; ReagentPlus®
• Impurities: ≤0.05% water; ≤0.10% acid (as acetic acid); ≤0.5% water
• Cation Traces: Al: ≤0.5 mg/kg; Ba: ≤0.1 mg/kg; Bi: ≤0.1 mg/kg; Ca: ≤0.5 mg/kg; Cd: ≤0.05 mg/kg; Co: ≤0.02 mg/kg; Cr: ≤0.02 mg/kg; Cu: ≤0.02 mg/kg; Fe: ≤0.1 mg/kg; K: ≤0.5 mg/kg; Li: ≤0.1 mg/kg; Mg: ≤0.1 mg/kg; Mn: ≤0.02 mg/kg; Mo: ≤0.1 mg/kg; Na: ≤0.5 mg/kg; Ni: ≤0.02 mg/kg; Pb: ≤0.1 mg/kg; Sr: ≤0.1 mg/kg; Zn: ≤0.5 mg/kg
• Linear Formula: CH3COCH2COOC2H5

DETAILS

MP Biomedicals - 02100019

1 ml = approx. 1.02 g

Sigma Aldrich - 537349

Packaging
1, 3 kg in poly bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 10912

Other Notes
prices for bulk quantities on request

Sigma Aldrich - 688983

Packaging
1 kg in poly bottle

Sigma Aldrich - W241512

Packaging
1 kg in glass bottle
1 sample in glass bottle
100 g in glass bottle
5 kg in poly drum

Sigma Aldrich - W241504

Packaging
1 kg in poly bottle
1 sample in glass bottle
5, 10, 25 kg in poly drum

REFERENCES

• Under the conditions of the classical acetoacetic ester route to methyl ketones [see, e.g.: Org. Synth. Coll., 1, 248, 351 (1941)], varying amounts of O-alkylation occur. Regioselective C-alkylation can be obtained by phase-transfer procedures: J. Org. Chem., 39, 3271 (1974). For improved alkylation using TBAB, see: Org. Prep. Proced. Int., 26, 469 (1994).
• Many techniques have been devised for the decarboalkoxylation of substituted ?-ketoesters (compare Diethyl malonate, A15468); for reviews, see: Synthesis, 805, 893 (1982). Enolisable ?-keto esters can be decarboalkoxylated by heating in toluene in the presence of a catalytic amount of DMAP. Other bases are ineffective: J. Org. Chem., 54, 3474 (1989).
• For use in diazo transfer reactions, see 4-Acetamidobenzenesulfonyl azide, L15916.