1,3-diethyl 2-ethylidenepropanedioate

• ChemBase ID: 90326
• Molecular Formular: C9H14O4
• Molecular Mass: 186.20506
• Monoisotopic Mass: 186.08920893
• SMILES: O(C(=O)C(=CC)C(=O)OCC)CC
• Canonical SMILES: CCOC(=O)C(=CC)C(=O)OCC
• InChI: InChI=1S/C9H14O4/c1-4-7(8(10)12-5-2)9(11)13-6-3/h4H,5-6H2,1-3H3
• InChIKey: LBBAWVLUOZVYCC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-diethyl 2-ethylidenepropanedioate
• IUPAC Traditional name: 1,3-diethyl 2-ethylidenepropanedioate
• Synonyms: Diethyl ethylidenemalonate; Ethylidenemalonic acid diethyl ester; Diethyl 2-ethylidenepropane-1,3-dioate; Diethyl 2-ethylidenemalonate; 亚乙基丙二酸二乙酯

Database IDs

• CAS Number: 1462-12-0
• EC Number: 215-965-5
• MDL Number: MFCD00009145
• Beilstein Number: 1773932
• PubChem SID: 162077146; 24894296
• PubChem CID: 73831

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.978896
• LogD (pH = 7.4): 1.978896
• Log P: 1.978896
• Molar Refractivity: 48.0746 cm^3
• Polarizability: 18.645124 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 115-116°C/17mm; 115-118 °C/17 mmHg(lit.); 115-118°C°C/17mm
• Flash Point: >110°C(230°F); >113 °C; >235.4 °F
• Density: 1.019; 1.019 g/mL at 25 °C(lit.)
• Refractive Index: 1.4420; n20/D 1.442(lit.)

Safety Information

• Storage Warning: Irritant
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves

Product Information

• Purity: 99%
• Linear Formula: CH3CH=C(CO2C2H5)2

DETAILS

Sigma Aldrich - D94801

Packaging
5 g in glass bottle

REFERENCES

• Addition of dibromocarbene (bromoform/NaOH) gives the dibromocyclopropane in good yield: Tetrahedron Lett., 26, 6353 (1985). Reaction with propargyl bromides in the presence of zinc leads to cyclopentenes: Synthesis, 150 (1978).
• Reaction with crotyltriisopropoxytitanium produces the anti-adduct as the major product: J. Chem. Soc., Chem. Commun., 386 (1985):