1,3-diethyl propanedioate

• ChemBase ID: 76796
• Molecular Formular: C7H12O4
• Molecular Mass: 160.16778
• Monoisotopic Mass: 160.07355886
• SMILES: O=C(OCC)CC(=O)OCC
• Canonical SMILES: CCOC(=O)CC(=O)OCC
• InChI: InChI=1S/C7H12O4/c1-3-10-6(8)5-7(9)11-4-2/h3-5H2,1-2H3
• InChIKey: IYXGSMUGOJNHAZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-diethyl propanedioate
• IUPAC Traditional name: diethyl malonate
• Synonyms: Diethyl propane-1,3-dioate; Diethyl malonate; Malonic acid diethyl ester; Diethyl malonate; Propanedioic acid diethyl ester; 胡萝卜酸二乙酯; 丙二酸二乙酯

Database IDs

• CAS Number: 105-53-3
• EC Number: 203-305-9
• MDL Number: MFCD00009195
• Beilstein Number: 774687
• Merck Index: 143823
• PubChem SID: 162041698; 24901030; 24894329
• PubChem CID: 7761
• CHEBI ID: 391281
• CHEMBL: 177114
• Chemspider ID: 13863636
• FEMA ID: 2375
• MeSH Name: Diethyl+malonate
• Unique Ingredient Identifier: 53A58PA183
• Wikipedia Title: Diethyl_malonate
• Council of Europe Number: 2106
• Flavis Number: 9.49

CALCULATED PROPERTIES

• Acid pKa: 12.359425
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.67428666
• LogD (pH = 7.4): 0.674282
• Log P: 0.6742868
• Molar Refractivity: 38.0232 cm^3
• Polarizability: 15.247779 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: negligible in water
• Apperance: colourless liquid
• Melting Point: -50 °C (223 K); -50°C; -50°C; -51°C; -51--50 °C(lit.)
• Boiling Point: 198-200°C; 199 °C (472 K); 199 °C(lit.); 199°C
• Flash Point: 194 °F; 200 °C; 90 °C; 90°C; 90°C(194°F)
• Density: 1.05 g/cm^3, liquid; 1.055; 1.055 g/mL at 25 °C(lit.); 1.06 g/ml
• Refractive Index: 1.413; 1.4140; n20/D 1.413; n20/D 1.413(lit.); n20/D 1.414
• Vapor Pressure: 1 mmHg ( 40 °C)
• Vapor Density: 5.52 (vs air)
• Organoleptic: fruity

Safety Information

• Storage Warning: Irritant
• RTECS: OO0700000
• European Hazard Symbols: Highly toxic (T+); Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 36; R:28-36/37/38
• Safety Statements: 26; S:28-29-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• Main Hazard: Harmful (X), Flammable (F)
• GHS Hazard statements: H227; H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Regulation Compliance: FDA 21 CFR (172.515)

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥97.0% (GC); ≥98%; ≥99.0% (GC); ≥99.5% (GC); 99%
• Grade: Halal; NI; puriss.; puriss. p.a.; purum; ReagentPlus®
• Shelf Life: (limited shelf life, expiry date on the label)
• Linear Formula: CH2(COOC2H5)2

DETAILS

MP Biomedicals - 05206008

MP Biomedicals Rare Chemical collection

Sigma Aldrich - W237507

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

Sigma Aldrich - D97754

Packaging
1, 2.5 kg in poly bottle
500 g in poly bottle
25 g in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

REFERENCES

• For phase-transfer monoalkylation of the active methylene group see, e.g. (18-crown-6): Synthesis, 37 (1977); and (BTEAC): Org. Prep. Proced. Int., 26, 469 (1994). Solid-liquid phase transfer alkylation has been promoted by microwave irradiation: Synth. Commun., 25,1761 (1995). Dialkylation can also occur in the presence of BTEAC: Synthesis, 54 (1985); Org. Synth. Coll., 7, 411 (1990), to give cyclopropane derivatives. Stereoselective alkylation has been achieved under particularly mild conditions with secondary alkyl mesylates in the presence of Cesium fluoride, 12885 in DMF; complete inversion occurs at the secondary alkyl carbon: J. Org. Chem., 60, 2627 (1995); see also: Synlett, 499 (1998).
• C-Acylation of malonic esters is normally carried out by reaction of the Mg derivative with an acid chloride. A convenient method using a combination of MgCl₂ and triethylamine was introduced by Rathke: J. Org. Chem., 50, 2622 (1985); see also Triethylamine, A12646 for discussion of this system:
  
• A number of procedures have been devised for the direct conversion of malonic esters to acetic esters (decarboalkoxylation), in a single step of which heating in wet DMSO is perhaps the simplest: J. Org. Chem., 43, 138 (1978). See also 1,4-Diazabicyclo[2.2.2]octane, A14003.
• Compare also Dimethyl malonate, A11007, Di-tert-butyl malonate, A12774, Dibenzyl malonate, A10844, and Isopropylidene malonate, A15603.
• Substituents can also be introduced by Michael addition; see e.g.: Org. Synth. Coll., 8, 467 (1993).
• Arylation occurs with aryl bromides in the presence of CuI: Gazz. Chim. Ital., 122, 511 (1992).