1,3-diethyl 2-(ethoxymethylidene)propanedioate

• ChemBase ID: 122910
• Molecular Formular: C10H16O5
• Molecular Mass: 216.23104
• Monoisotopic Mass: 216.09977361
• SMILES: C(=COCC)(C(=O)OCC)C(=O)OCC
• Canonical SMILES: CCOC=C(C(=O)OCC)C(=O)OCC
• InChI: InChI=1S/C10H16O5/c1-4-13-7-8(9(11)14-5-2)10(12)15-6-3/h7H,4-6H2,1-3H3
• InChIKey: LTMHNWPUDSTBKD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-diethyl 2-(ethoxymethylidene)propanedioate
• IUPAC Traditional name: 1,3-diethyl 2-(ethoxymethylidene)propanedioate
• Synonyms: Diethyl ethoxymethylenemalonate; diethyl 2-(ethoxymethylene)malonate; Diethyl (ethoxymethylene)malonate; 2-(Ethoxymethylene)propanedioic Acid 1,3-Diethyl Ester; (Ethoxymethylene)malonic Acid Diethyl Ester; (Ethoxymethylene)propanedioic Acid Diethyl Ester; Diethyl[(ethyloxy)methylidene]propanedioate; Ethyl 3-Ethoxy-2-(ethoxymethylene)-3-oxopropanoate; NSC 62117; NSC 9068; Diethyl Ethoxymethylidenemalonate; Diethyl EthoxyMethyleneMalonate; Ethoxymethylenemalonic acid diethyl ester; Ethoxymethylenepropanedioic acid diethyl ester; 乙氧基亚甲基丙二酸二乙酯; 乙氧基甲叉丙二酸二乙酯; 乙氧亚甲基丙二酸二乙酯

Database IDs

• CAS Number: 87-13-8
• EC Number: 201-725-7
• MDL Number: MFCD00009148
• Beilstein Number: 880058
• PubChem SID: 162217263; 24894294; 24845377
• PubChem CID: 6871

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.471484
• LogD (pH = 7.4): 1.471484
• Log P: 1.471484
• Molar Refractivity: 53.8786 cm^3
• Polarizability: 21.211697 Å^3
• Polar Surface Area: 61.83 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Colourless Liquid
• Melting Point: -33°C
• Boiling Point: 136-139°C/10mm; 279-281 °C(lit.); 279-283 °C(lit.)
• Flash Point: 144 °C; 144°C(291°F); 291.2 °F
• Density: 1.07 g/mL at 25 °C(lit.); 1.080; 1.080 g/mL at 20 °C(lit.)
• Refractive Index: 1.4620; n20/D 1.462(lit.); n20/D 1.463

Safety Information

• Storage Condition: Refrigerator
• RTECS: OO1100000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 22-36/37/38; 22-36/38-42/43
• Safety Statements: 23-24-26-36/37-45; 26-36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335; H334-H315-H319-H317-H303
• GHS Precautionary statements: P261-P305 + P351 + P338; P285-P261-P305+P351+P338-P302+P352-P321-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥99.0% (GC); 95+%; 97%; 98+%; 99%
• Grade: purum
• Linear Formula: C2H5OCH=C(COOC2H5)2

DETAILS

Sigma Aldrich - D94208

Packaging
5, 100, 500 g in glass bottle

Toronto Research Chemicals - D444300

Intermediate in the production of Flumequine

REFERENCES

• Sato, M., et al.: J. Med. Chem., 52, 4869 (2009)
• Can be converted to the unstable diethyl methylenemalonate by catalytic reduction and elimination of ethanol on distillation, see: Org. Synth. Coll., 4, 298 (1963).
• Stable equivalent of the ɑ-formylmalonate, valuable synthetic building block, particularly in heterocyclic syntheses. Review: Adv. Het. Chem., 54, (1992).
• Has been used for the protection of the amino group of ɑ-amino acids, allowing clean esterification by O-alkylation. The protecting group can be removed using bromine in chloroform: Synthesis, 544 (1989):
  
• For N-protection of aminoglycosides prior to O-acetylation, see: J. Carbohydr. Chem., 14, 1133 (1995). Chlorine in chloroform at 0^oC was used for deprotection.