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609-09-6 molecular structure
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1,3-diethyl 2-oxopropanedioate

ChemBase ID: 8029
Molecular Formular: C7H10O5
Molecular Mass: 174.1513
Monoisotopic Mass: 174.05282342
SMILES and InChIs

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

Cite this record

CBID:8029 http://www.chembase.cn/molecule-8029.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

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

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 1.4975388  LogD (pH = 7.4) 1.4975388 
Log P 1.4975388  Molar Refractivity 38.82 cm3
Polarizability 15.412765 Å3 Polar Surface Area 69.67 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
ca -70°C expand Show data source
Boiling Point
208-210 °C(lit.) expand Show data source
208-210°C expand Show data source
208-210°C expand Show data source
95-98 °C/12 mmHg(lit.) expand Show data source
96-98°C expand Show data source
Flash Point
>110°C(230°F) expand Show data source
113 °C expand Show data source
235.4 °F expand Show data source
Density
0.927 expand Show data source
1.128 g/mL at 20 °C(lit.) expand Show data source
1.142 expand Show data source
1.142 g/mL at 25 °C(lit.) expand Show data source
Refractive Index
1.4150 expand Show data source
1.4175 expand Show data source
n20/D 1.415 expand Show data source
n20/D 1.415(lit.) expand Show data source
Storage Warning
IRRITANT, MOISTURE SENSITIVE expand Show data source
Irritant/Moisture Sensitive expand Show data source
Moisture Sensitive expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
TSCA Listed
true expand Show data source
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves expand Show data source
Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US) expand Show data source
Purity
≥96.0% (GC) expand Show data source
95% expand Show data source
95+% expand Show data source
Grade
purum expand Show data source
Certificate of Analysis
Download expand Show data source
Appearance
green-yellow liquid expand Show data source
Linear Formula
CO(CO2C2H5)2 expand Show data source
CO(COOC2H5)2 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich
MP Biomedicals - 05215003 external link
MP Biomedicals Rare Chemical collection
Sigma Aldrich - D97401 external link
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 external link
Other Notes
Reactions with olefins to allylcarboxylic acids1; DA cycloaddition to heterocycles2,3

REFERENCES

REFERENCES

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  • • 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).
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PATENTS

PATENTS

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INTERNET

INTERNET

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