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517135

Sigma-Aldrich

Diethyl carbonate

greener alternative

anhydrous, ≥99%

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Synonym(s):
Diatol, Eufin, H-DEC
Linear Formula:
(C2H5O)2CO
CAS Number:
105-58-8
Molecular Weight:
118.13
Beilstein:
956591
EC Number:
203-311-1
MDL number:
MFCD00009107
UNSPSC Code:
12352100
PubChem Substance ID:
24873944
NACRES:
NA.22

grade

anhydrous

Quality Level

100

vapor density

4.1 (vs air)

vapor pressure

10 mmHg ( 23.8 °C)
59 mmHg ( 37.8 °C)

Assay

≥99%

greener alternative product characteristics

Less Hazardous Chemical Syntheses
Safer Solvents and Auxiliaries
Design for Degradation
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

impurities

<0.002% water
<0.005% water (100 mL)

refractive index

n20/D 1.384 (lit.)

bp

126-128 °C (lit.)

mp

−43 °C (lit.)

solubility

water: insoluble

density

0.975 g/mL at 25 °C (lit.)

greener alternative category

Aligned,

SMILES string

O=C(OCC)OCC

InChI

1S/C5H10O3/c1-3-7-5(6)8-4-2/h3-4H2,1-2H3

InChI key

OIFBSDVPJOWBCH-UHFFFAOYSA-N

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General description

Diethyl carbonate is an dialkylcarbonate. The synthesis of diethyl carbonate (DEC) from urea and ethanol has been investigated.
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Application

Diethyl carbonate may be used in the following studies:
  • Synthesis of β-enamino esters.
  • Synthesis of carbamates and unsymmetrical alkyl carbonates, via reaction with aliphatic amines or alcohols by using a hybrid organic-inorganic material prepared by anchoring TBD to MCM-41 silica.
  • As solvent in ruthenium catalyzed direct functionalisation of arene C-H bonds by aryl halides.
  • To compose the commercial liquid electrolyte for lithium ion batteries.
  • Homogeneous alkoxycarbonylation of cellulose.

Features and Benefits

Greener chemical

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

WGK

WGK 1

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A versatile route to β-enamino esters by acylation of lithium enamines with diethyl carbonate or benzyl chloroformate.
Bartoli G, et al.
Tetrahedron, 51(31), 8613-8622 (1995)
Catalytic activity of MCM-41-TBD in the selective preparation of carbamates and unsymmetrical alkyl carbonates from diethyl carbonate.
Carloni S, et al.
J. Catal., 205(1), 199-204 (2002)
Sara R Labafzadeh et al.
ChemSusChem, 8(1), 77-81 (2014-11-08)
Dialkylcarbonates are viewed as low-cost, low-toxicity reagents, finding application in many areas of green chemistry. Homogeneous alkoxycarbonylation of cellulose was accomplished by applying dialkycarbonates (dimethyl and diethyl carbonate) in the ionic liquid-electrolyte trioctylphosphonium acetate ([P8881 ][OAc])/DMSO or 1-ethyl-3-methylimidazolium acetate ([emim][OAc]).
Diethyl carbonate as a solvent for ruthenium catalysed C-H bond functionalisation.
Arockiam P, et al.
Green Chemistry, 11(11), 1871-1875 (2009)
Zhiyuan Zeng et al.
Faraday discussions, 176, 95-107 (2015-01-20)
We study the lithiation of a Au electrode in an electrochemical liquid cell using transmission electron microscopy (TEM). The commercial liquid electrolyte for lithium ion batteries (1 M lithium hexafluorophosphate LiPF6 dissolved in 1 : 1 (v/v) ethylene carbonate (EC) and diethyl
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