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616-38-6

Basic Information
CAS No.: 616-38-6
Name: Dimethyl carbonate
Article Data: 337
Molecular Structure:
Molecular Structure of 616-38-6 (Dimethyl carbonate)
Formula: C3H6O3
Molecular Weight: 90.0788
Synonyms: Methyl carbonate ((MeO)2CO);Carbonic acid, dimethyl ester;Dimethyl carbonate [UN1161] [Flammable liquid];Carbonic acid,esters,dimethyl ester;Methyl Carbonate;
EINECS: 210-478-4
Density: 1.024 g/cm3
Melting Point: 2-4 °C(lit.)
Boiling Point: 90.5 °C at 760 mmHg
Flash Point: 18.333 °C
Solubility: 139 g/L in water
Appearance: colourless liquid
Hazard Symbols: FlammableF
Risk Codes: 11
Safety: 9-16
Transport Information: UN 1161 3/PG 2
PSA: 35.53000
LogP: 0.39920
Synthetic route
67-56-1

methanol

201230-82-2

carbon monoxide

616-38-6

carbonic acid dimethyl ester

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; triethylamine at 90 - 100℃; under 40 - 80 Torr;100%
With <2>*H2O at 120℃; under 15200 Torr; for 7h;45.2%
With sodium selenite; oxygen at 100℃; under 37503.8 Torr; for 2h; Reagent/catalyst; Temperature;32.9%
96-49-1

[1,3]-dioxolan-2-one

67-56-1

methanol

A

107-21-1

ethylene glycol

B

616-38-6

carbonic acid dimethyl ester

Conditions
ConditionsYield
anion exchanging resin at 80.4 - 98℃; for 6h; Product distribution / selectivity;A 99%
B 99.7%
potassium hydroxide In water at 98℃; under 838.584 Torr; for 500 - 6000h; Product distribution / selectivity; Heating / reflux;A n/a
B 99.88%
potassium hydroxide at 98 - 130℃; under 784.578 - 838.584 Torr; for 500 - 6000h; Product distribution / selectivity; Heating / reflux;A n/a
B 99.99%
96-49-1

[1,3]-dioxolan-2-one

67-56-1

methanol

A

107-21-1

ethylene glycol

B

616-38-6

carbonic acid dimethyl ester

C

111-46-6

diethylene glycol

Conditions
ConditionsYield
potassium hydroxide at 63.8 - 98℃; for 6.7h; Product distribution / selectivity;A 99.1%
B 99.8%
C n/a
sodium hydroxide at 49.8 - 56.2℃; under 342.034 Torr; Product distribution / selectivity; Industry scale;A 91.3%
B 91.3%
C n/a
potassium hydroxide at 47 - 56℃; under 228.023 - 342.034 Torr; Product distribution / selectivity; Industry scale;A 90.5%
B 90.5%
C n/a
at 55.9 - 56℃; under 342.034 Torr; Product distribution / selectivity; Industry scale;A 38.9%
B 38.9%
C n/a
67-56-1

methanol

79-22-1

methyl chloroformate

616-38-6

carbonic acid dimethyl ester

Conditions
ConditionsYield
With 1-methyl-1H-imidazole In Diethyl carbonate at 0 - 20℃; for 1h;98.2%
at 30℃; Rate constant; Mechanism; var. conc, presence of var. salts (LiCl, (CH3)4NCl, (C2H5)4NBr);
at 30℃; Thermodynamic data; Rate constant; ΔH(excit.), -ΔS(excit.);
67-56-1

methanol

116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

616-38-6

carbonic acid dimethyl ester

Conditions
ConditionsYield
Stage #1: methanol With Tetraethylene glycol dimethyl ether; potassium carbonate at 10 - 30℃;
Stage #2: 1,1,1,3,3,3-hexachloro-propan-2-one at 30 - 75℃; Reagent/catalyst;
97%
67-56-1

methanol

124-38-9

carbon dioxide

616-38-6

carbonic acid dimethyl ester

Conditions
ConditionsYield
With 2-Cyanopyridine; cerium(IV) oxide at 119.84℃; under 37503.8 Torr; for 16h; Reagent/catalyst; Pressure; Temperature; Autoclave;96%
With 2-pyrazine carbonitrile at 20 - 50℃; under 15001.5 - 45004.5 Torr; for 50h; Reagent/catalyst; Temperature; Pressure; Autoclave;95%
With 2-Cyanopyridine; cerium(IV) oxide at 119.84℃; under 37503.8 Torr; for 12h; Autoclave;94%
96-49-1

[1,3]-dioxolan-2-one

67-56-1

methanol

616-38-6

carbonic acid dimethyl ester

Conditions
ConditionsYield
With graphitic carbon nitride at 119.84℃; for 4h; Catalytic behavior; Concentration; Reagent/catalyst; Time;93%
With 2-hydroxymethyl-1-methyl-3-n-buthylimidazole bromide; potassium carbonate at 60℃; for 1h; Green chemistry;90%
With mesoporous carbon nitride detemplated by 0.5 M NaOH solution at 160℃; under 4500.45 Torr; for 6h; Catalytic behavior; Knoevenagel Condensation; Autoclave;90.7%
108-32-7

1,2-propylene cyclic carbonate

67-56-1

methanol

616-38-6

carbonic acid dimethyl ester

Conditions
ConditionsYield
at 90℃; for 3h; Temperature; Time;93%
With calcined hollow titanium silicon molecular sieve modified with sodium carbonate and ammonium dihydrogen phosphate In water at 100℃; for 8h; Time; Reagent/catalyst; Temperature; Autoclave;74%
at 140℃; for 6h;35%
67-56-1

methanol

106729-72-0

(2-hydroxyethyl) methyl carbonate

A

107-21-1

ethylene glycol

B

616-38-6

carbonic acid dimethyl ester

Conditions
ConditionsYield
With film supported Penicillium expansum at 60℃; for 48h; Reagent/catalyst; Concentration; Temperature; Time; Enzymatic reaction;A 93%
B 93%
67-56-1

methanol

584-07-6

methyl N-hydroxycarbamate

616-38-6

carbonic acid dimethyl ester

Conditions
ConditionsYield
With lead dioxide In dichloromethane at 40℃; for 0.166667h;92.1%
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    Product identifiers Product name : Dimethyl carbonate CAS-No. : 616-38-6 EC : 210-478-4 Relevant identified uses of the substance or mixture and uses advised against Identified use

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Chemistry

Molecule structure of Dimethyl carbonate (CAS NO.616-38-6):

IUPAC Name: Dimethyl carbonate 
Molecular Weight: 90.07794 g/mol
Molecular Formula: C3H6O3 
Density: 1.024 g/cm3 
Melting Point: 2-4 °C(lit.)
Boiling Point: 90.5 °C at 760 mmHg 
Flash Point: 18.3 °C
Index of Refraction: 1.361
Molar Refractivity: 19.46 cm3
Molar Volume: 87.9 cm3
Surface Tension: 24.6 dyne/cm
Enthalpy of Vaporization: 33.05 kJ/mol
Vapour Pressure: 56 mmHg at 25 °C 
Storage Temp.: flammables area
Water Solubility: 139 g/L
XLogP3-AA: 0.5
H-Bond Acceptor: 3
Rotatable Bond Count: 2
Exact Mass: 90.031694
MonoIsotopic Mass: 90.031694
Topological Polar Surface Area: 35.5
Heavy Atom Count: 6
Canonical SMILES: COC(=O)OC
InChI: InChI=1S/C3H6O3/c1-5-3(4)6-2/h1-2H3
InChIKey: IEJIGPNLZYLLBP-UHFFFAOYSA-N
EINECS: 210-478-4
Product Categories: Pharmaceutical Intermediates; Organics; Alternative Energy; Electrolytes; Materials Science; Anhydrous Grade SolventsSolvents; Solvent Bottles; Solvents; Sure/Seal Bottles; Carbonates; Carbonyl Compounds; Organic Building Blocks 

Uses

 Dimethyl carbonate (CAS NO.616-38-6) is a carbonate ester which has recently found use as a methylating reagent. It is also used as intermediate of herbicide.

Production

 Dimethyl carbonate (CAS NO.616-38-6) is now prepared from catalytic oxidative carbonylation of methanol with carbon monoxide and oxygen, instead of from phosgene.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 800mg/kg (800mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 361, 1979.
mouse LD50 oral 6gm/kg (6000mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 361, 1979.
rabbit LD50 skin > 5gm/kg (5000mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 361, 1979.
rat LD50 intraperitoneal 1600mg/kg (1600mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 361, 1979.
rat LD50 oral 13gm/kg (13000mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 361, 1979.

Safety Profile

Hazard Codes: FlammableF
Risk Statements: 11 
R11:Highly flammable.
Safety Statements: 9-16 
S9:Keep container in a well-ventilated place. 
S16:Keep away from sources of ignition.
RIDADR: UN 1161 3/PG 2
WGK Germany: 1
RTECS: FG0450000
HazardClass: 3
PackingGroup: II

Specification

 Dimethyl carbonate (CAS NO.616-38-6) is also named as AI3-14705 ; HSDB 6928 ; Methyl carbonate ; Methyl carbonate ((MeO)2CO) ; NSC 9371 ; Carbonic acid, dimethyl ester . Dimethyl carbonate is colourless liquid with a pleasant odor. It is slightly soluble in water and highly flammable. Dimethyl carbonate reacts with acids to liberate heat along with methanol and carbon dioxide. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction with caustic solutions. Flammable hydrogen is generated by mixing with alkali metals and hydrides. It may cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. It will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated.