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517135

Sigma-Aldrich

Diethyl carbonate

greener alternative

anhydrous, ≥99%

Synonym(s):

Diatol, Eufin, H-DEC

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About This Item

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
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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

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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.)

functional group

carbonate

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.[1] The synthesis of diethyl carbonate (DEC) from urea and ethanol has been investigated.[2]
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Application

Diethyl carbonate may be used in the following studies:
  • Synthesis of β-enamino esters.[3]
  • 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.[4]
  • As solvent in ruthenium catalyzed direct functionalisation of arene C-H bonds by aryl halides.[5]
  • To compose the commercial liquid electrolyte for lithium ion batteries.[6]
  • Homogeneous alkoxycarbonylation of cellulose.[1]

Features and Benefits

Greener chemical

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

77.0 °F - closed cup

Flash Point(C)

25 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBS2643
SHBR4850
SHBQ1699
SHBN7328
SHBM9866

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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)
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]).
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)
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
Diethyl carbonate as a solvent for ruthenium catalysed C-H bond functionalisation.
Arockiam P, et al.
Green Chemistry, 11(11), 1871-1875 (2009)
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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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