1,3-diethyl 2-oxopropanedioate

• ChemBase ID: 8029
• Molecular Formular: C7H10O5
• Molecular Mass: 174.1513
• Monoisotopic Mass: 174.05282342
• SMILES: CCOC(=O)C(=O)C(=O)OCC
• Canonical SMILES: CCOC(=O)C(=O)C(=O)OCC
• InChI: InChI=1S/C7H10O5/c1-3-11-6(9)5(8)7(10)12-4-2/h3-4H2,1-2H3
• InChIKey: DBKKFIIYQGGHJO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-diethyl 2-oxopropanedioate
• IUPAC Traditional name: 1,3-diethyl 2-oxopropanedioate
• Synonyms: Diethyl 2-oxopropane-1,3-dioate; Diethyl ketomalonate; Diethyl 2-oxomalonate 97%; Diethyl ketomalonate; Diethyl mesoxalate; Ketomalonic acid diethyl ester; Diethyl ketomalonate; Diethyl mesoxalate; Diethyl oxomalonate; Diethyl mesoxalate; 2-氧代丙二酸二乙酯; 二乙基双乙烯酯; 酮基丙二酸二乙酯; 酮基丙二酸二乙酯; 丙酮二酸二乙酯

Database IDs

• CAS Number: 609-09-6
• EC Number: 210-176-2
• MDL Number: MFCD00009121
• Beilstein Number: 971873
• Merck Index: 145913
• PubChem SID: 24894323; 160971336; 24883047
• PubChem CID: 69105

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.4975388
• LogD (pH = 7.4): 1.4975388
• Log P: 1.4975388
• Molar Refractivity: 38.82 cm^3
• Polarizability: 15.412765 Å^3
• Polar Surface Area: 69.67 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ca -70°C
• Boiling Point: 208-210 °C(lit.); 208-210°C; 208-210°C; 95-98 °C/12 mmHg(lit.); 96-98°C
• Flash Point: >110°C(230°F); 113 °C; 235.4 °F
• Density: 0.927; 1.128 g/mL at 20 °C(lit.); 1.142; 1.142 g/mL at 25 °C(lit.)
• Refractive Index: 1.4150; 1.4175; n20/D 1.415; n20/D 1.415(lit.)

Safety Information

• Storage Warning: IRRITANT, MOISTURE SENSITIVE; Irritant/Moisture Sensitive; Moisture Sensitive
• German water hazard class: 3
• TSCA Listed: true; 是
• Personal Protective Equipment: Eyeshields, Gloves; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

Product Information

• Purity: ≥96.0% (GC); 95%; 95+%
• Grade: purum
• Appearance: green-yellow liquid
• Linear Formula: CO(CO2C2H5)2; CO(COOC2H5)2

DETAILS

MP Biomedicals - 05215003

MP Biomedicals Rare Chemical collection

Sigma Aldrich - D97401

Packaging
5, 25 g in glass bottle
Application
Reagent employed in Wittig and Aza-Wittig reactions for synthesis of triazoles1 and 2-azadienes,2 respectively.

Sigma Aldrich - 63970

Other Notes
Reactions with olefins to allylcarboxylic acids1; DA cycloaddition to heterocycles2,3

REFERENCES

• The carbonyl group behaves as a heterodienophile towards simple dienes. Curtius degradation of the gem-diester to carbonyl completes a synthesis of ?-unsaturated δ-lactones: Rocz. Chem., 38, 707 (1964); J. Am. Chem. Soc., 97, 6892 (1975); J. Org. Chem., 42, 4095 (1977):
  
• Ene-addition to alkenes occurs at the less-substituted carbon. Oxidative degradation leads to ?-unsaturated carboxylic acids: J. Am. Chem. Soc., 102, 2473 (1980); 106, 3797 (1984):
  
• For asymmetric Diels-Alder reaction, see: J. Chem. Soc., Chem. Commun., 676 (1987). For addition to aza-dienes, see: Tetrahedron Lett, 30, 2685 (1989).
• Thus, the reagent could be regarded as a CO₂ equivalent in both the above sequences.
• Undergoes the Baylis-Hillman reaction in which a carbanionic species, generated by the reversible addition of 1,4-Diazabicyclo[2.2.2]octane, A14003, to a Michael acceptor, adds to the carbonyl group: Synth. Commun., 19, 2461 (1989).
• Reacts with activated arenes under Friedel-Crafts conditions, or with aryllithium or Grignard derivatives, to give aryl hydroxymalonates, hydrolysis and decarboxylation of which gives substituted mandelic acids: Org. Synth. Coll., 3, 326 (1955). Alternatively, they may be transformed reductively to arylmalonates and hence to ester enolates: J. Org. Chem., 47, 4692 (1982).