1,4-diethyl butanedioate

• ChemBase ID: 108857
• Molecular Formular: C8H14O4
• Molecular Mass: 174.19436
• Monoisotopic Mass: 174.08920893
• SMILES: CCOC(=O)CCC(=O)OCC
• Canonical SMILES: CCOC(=O)CCC(=O)OCC
• InChI: InChI=1S/C8H14O4/c1-3-11-7(9)5-6-8(10)12-4-2/h3-6H2,1-2H3
• InChIKey: DKMROQRQHGEIOW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,4-diethyl butanedioate
• IUPAC Traditional name: diethyl succinate
• Synonyms: DIETHYL SUCCINATE; Diethyl succinate; Butanedioic acid diethyl ester; Succinic acid diethyl ester; 丁二酸二乙酯

Database IDs

• CAS Number: 123-25-1
• EC Number: 204-612-0
• MDL Number: MFCD00009208
• Beilstein Number: 907645
• Merck Index: 148869
• PubChem SID: 24847094; 24901032; 24848485; 162095651; 24846069
• PubChem CID: 31249
• FEMA ID: 2377
• Council of Europe Number: 438
• Flavis Number: 9.444

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.6069211
• LogD (pH = 7.4): 0.6069211
• Log P: 0.6069211
• Molar Refractivity: 42.5724 cm^3
• Polarizability: 17.06897 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -20 °C(lit.); -21°C; 32 - 40°C
• Boiling Point: 216-218°C; 218 °C(lit.)
• Flash Point: 195.8 °F; 90°C(194°F); 91 °C
• Density: 1.043; 1.047 g/mL at 25 °C(lit.)
• Refractive Index: 1.4200; n20/D 1.42(lit.); n20/D 1.420
• Vapor Density: 6 (vs air)
• Hydrophobicity(logP): 1.482
• Organoleptic: apple; apricot; chocolate; cranberry; grape; musty; floral; fruity; peach; pear; wine-like; waxy; earthy

Safety Information

• RTECS: WM7400000
• German water hazard class: 2
• TSCA Listed: 是
• GHS Hazard statements: H227
• GHS Precautionary statements: P210-P280-P370+P378A-P403+P235-P501A
• 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: EU Regulation 1334/2008 & 178/2002; FCC; FDA 21 CFR (172.515)

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥99%; ≥99.0% (GC); ≥99.5% (GC); 95%; 97%; 98%; 99%
• Grade: analytical standard; FG; Halal; Kosher; NI; purum; ReagentPlus®
• Shelf Life: (limited shelf life, expiry date on the label)
• Linear Formula: C2H5OCOCH2CH2COOC2H5

DETAILS

MP Biomedicals - 05209005

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 112402

Packaging
1 kg in poly bottle
250 g in poly bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - W237701

Biochem/physiol Actions
Taste at 10-100 ppm
General description
Natural Occurrence: Apple, cocoa, grape, brandy, whiskey and wine.
Packaging
1 kg in poly bottle
5kg, 10kg packaged in closed-head poly drums; sample, 1kg packaged in glass bottles
1 sample in glass bottle
5, 10, 25 kg in poly drum

REFERENCES

• Undergoes the Stobbe condensation with carbonyl compounds to give alkylidene derivatives; review: Org. React., 6, 1 (1951). For the Stobbe condensation with benzophenone to give the monoester of the product, see: Org. Synth. Coll., 4, 132 (1963).
• For an example of the acyloin condensation under silylating conditions to give 2-hydroxycyclobutanone, see: Org. Synth. Coll., 6, 167 (1988). An alternative work-up with bromine leads directly to 1,2-cyclobutanedione: Org. Synth. Coll., 7, 112 (1990):