diethyl carbonate

• ChemBase ID: 127003
• Molecular Formular: C5H10O3
• Molecular Mass: 118.1311
• Monoisotopic Mass: 118.06299418
• SMILES: O=C(OCC)OCC
• Canonical SMILES: CCOC(=O)OCC
• InChI: InChI=1S/C5H10O3/c1-3-7-5(6)8-4-2/h3-4H2,1-2H3
• InChIKey: OIFBSDVPJOWBCH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl carbonate
• IUPAC Traditional name: diethyl carbonate
• Synonyms: carbonic ether; ethyl carbonate; Eufin; Diethyl carbonate; Diethyl carbonate; Carbonic acid diethyl ester; 碳酸二乙酯

Database IDs

• CAS Number: 105-58-8
• EC Number: 203-311-1
• MDL Number: MFCD00009107
• Beilstein Number: 956591
• Merck Index: 143780
• PubChem SID: 24873944; 24859279; 24859278; 162221326; 24894264
• PubChem CID: 7766
• Chemspider ID: 7478
• Wikipedia Title: Diethyl_carbonate

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.2554554
• LogD (pH = 7.4): 1.2554554
• Log P: 1.2554554
• Molar Refractivity: 28.5336 cm^3
• Polarizability: 11.458225 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Insoluble in water
• Apperance: Clear liquid
• Melting Point: -43 °C(lit.); -43 °C; -43°C
• Boiling Point: 126-128 °C(lit.); 126–128 °C; 126-128°C
• Flash Point: 25 °C; 31°C(87°F); 33 °C; 77 °F
• Density: 0.975; 0.975 g/cm^3; 0.975 g/mL at 25 °C(lit.)
• Refractive Index: 1.3845; n20/D 1.384; n20/D 1.384(lit.); n20/D 1.385
• Vapor Pressure: 10 mmHg ( 23.8 °C); 59 mmHg ( 37.8 °C)
• Vapor Density: 4.1 (vs air)

Safety Information

• Storage Warning: Moisture Sensitive
• RTECS: FF9800000
• European Hazard Symbols: Irritant (Xi)
• UN Number: 2366; UN2366
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10-36/37/38; R11
• Safety Statements: 16-23-26-36; 23-26-37-60; S9 S16 S29 S33
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H315-H319-H335
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2366 3/PG 3

Product Information

• Purity: ≥98.0% (GC); ≥99%; ≥99.5% (GC); 99%; 99+%
• Grade: anhydrous; puriss.; purum
• Impurities: <0.002% water; <0.005% water(100 mL)
• Linear Formula: (C2H5O)2CO

DETAILS

Sigma Aldrich - D91551

Packaging
1, 4 L in glass bottle
18 L in VerSA-Flow™
250 mL in glass bottle

Sigma Aldrich - 517135

Packaging
1 L in Sure/Seal™
100 mL in Sure/Seal™

REFERENCES

• Carboethoxylates carbanions derived from ketones, nitriles, esters, etc. For examples, see: Org. Synth. Coll., 4, 461 (1963); 5, 198 (1973); 6, 611 (1988). Arylacetic esters are converted to arylmalonic diesters: Org. Prep. Proced. Int., 6, 5 (1974). The dianions of carboxylic acids can be carboethoxylated with diethyl carbonate (or Ethyl chloroformate, L06311), to give monoesters of malonic acids: Tetrahedron Lett., 2721 (1974).
• For use as an alkylating agent for alcohols, phenols, thiols, etc., see Dimethyl carbonate, A13104.
• 1,3-Diols undergo dehydration to give oxetanes; see, e.g.: Tetrahedron Lett., 24, 5571 (1983):