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D152927

Sigma-Aldrich

Dimethyl carbonate

greener alternative

ReagentPlus®, 99%

Synonym(s):

Carbonic acid dimethyl ester

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About This Item

Linear Formula:
(CH3O)2CO
CAS Number:
616-38-6
Molecular Weight:
90.08
Beilstein:
635821
EC Number:
210-478-4
MDL number:
MFCD00008420
UNSPSC Code:
12352100
PubChem Substance ID:
57654072
NACRES:
NA.21

vapor density

3.1 (vs air)

Quality Level

200

vapor pressure

18 mmHg ( 21.1 °C)

product line

ReagentPlus®

Assay

99%

form

liquid

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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refractive index

n20/D 1.368 (lit.)

bp

90 °C (lit.)

mp

2-4 °C (lit.)

density

1.069 g/mL at 25 °C (lit.)

greener alternative category

, Aligned

SMILES string

O=C(OC)OC

InChI

1S/C3H6O3/c1-5-3(4)6-2/h1-2H3

InChI key

IEJIGPNLZYLLBP-UHFFFAOYSA-N

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General description

Dimethyl carbonate (DMC) is a versatile, non-toxic, biodegradable reagent with tunable chemical reactivity. It serves as a green alternative to dimethyl sulfate or methyl halides and phosgene for methylation and carboxylation reactions. The base-catalyzed reaction between carbon dioxide and methanol to form DMC has been studied. Various thermodynamic parameters of DMC have been reported.

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Application

Dimethyl carbonate may be used to synthesize:
  • Methyl phenyl carbonate by transesterification with phenol.
  • Diphenyl carbonate by transesterification with methyl phenyl carbonate.
  • Methyl carbamates, a raw material for isocyanate synthesis.
  • Tetramethoxysilane by reacting with silica at 550-600K.

Features and Benefits

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Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Flame
GHS02

Signal Word

Danger

Hazard Statements

H225

Hazard Classifications

Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

60.8 °F - closed cup

Flash Point(C)

16 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB0749
MKCW5981
MKCV7668
MKCW1721
MKCV8786

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Direct synthesis of dimethyl carbonate from carbon dioxide and methanol catalyzed by base.
Fang S and Fujimoto K.
Applied Catalysis A: General, 142(1), L1-L3 (1996)
Thermodynamic Properties of Dimethyl Carbonatea).
Zhou Y, et al.
Journal of Physical and Chemical Reference Data, 40(4), 043106-043106 (2011)
Zul Ilham et al.
Bioresource technology, 101(8), 2735-2740 (2009-11-26)
This study reports on a novel two-step process for biodiesel production consisting of hydrolysis of oils in sub-critical water and subsequent supercritical dimethyl carbonate esterification. This process found to occur optimally at the sub-critical water treatment (270 degrees Celsius/27 MPa)
Catalysis in the production and reactions of dimethyl carbonate, an environmentally benign building block.
Ono Y.
Applied Catalysis A: General, 155(2), 133-166 (1997)
Jana Engeldinger et al.
Physical chemistry chemical physics : PCCP, 14(7), 2183-2191 (2011-11-18)
The simultaneous combination of steady state isotopic transient kinetic analysis (SSITKA) with diffuse reflectance Fourier transform spectroscopy (DRIFTS) and mass spectrometric (MS) analysis was applied to study the oxidative carbonylation of methanol (MeOH) to dimethyl carbonate (DMC) on a CuY
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