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616-38-6 - Dimethyl carbonate, 99% - Carbonic acid dimethyl ester - Methyl carbonate - A13104 - Alfa Aesar

A13104 Dimethyl carbonate, 99%

CAS Number
616-38-6
Synonyms
Carbonic acid dimethyl ester
Methyl carbonate

Size Price ($) Quantity Availability
100g 13.95
500g 35.33
2500g 113.30
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Dimethyl carbonate, 99%

MDL
MFCD00008420
EINECS
210-478-4

Chemical Properties

Formula
C3H6O3
Formula Weight
90.08
Melting point
ca 4°
Boiling Point
90°
Flash Point
16°(61°F)
Density
1.070
Refractive Index
1.3680
Sensitivity
Moisture Sensitive
Solubility
Miscible with alcohol and ether. Immiscible with water.

Applications

Dimethyl carbonate is used as a solvent in organic synthesis and considered as a replacement for solvent like methyl ethyl ketone, tert-butyl acetate and parachlorobenzotrifluoride. It is involved as an intermediate in the preparation of diphenylcarbonate, which in turn is used as a key raw material for the synthesis of Bisphenol-A-polycarbonate. It is also used as a 'green' methylating agent involved in the methylation of aniline, phenols and carboxylic acids. It can be used as a fuel additive due to its high oxygen content. It also finds applications related to supercapacitors and lithium batteries.

Notes

Air and moisture sensitive. Keep container tightly closed in a dry and well-ventilated place. Incompatible with oxidizing agents, strong acids and strong bases.

Literature References

Conversion of a ketone to its methoxycarbonyl derivative has been used to change the preferred site of chlorination to the less-substituted carbon atom: Synthesis, 188 (1987):

Grignard reagents react in THF to give methyl esters, providing a high-yield, one-pot synthesis of carboxylic esters from alkyl or aryl halides: Synth. Commun., 20, 3273 (1990).

Useful alkylating agent. Although less reactive, dimethyl carbonate has the advantage of much lower toxicity than the more usual sulfate or iodide. In the presence of K2CO3 and 18-crown-6, alcohols, phenols, thiols, imidazoles, etc. can be methylated: Synthesis, 382 (1986). For K2CO3 promoted alkylation of active methylene compounds at 180-220o (pressure), see: Rec. Trav. Chim., 115, 256 (1996); Org. Synth., 76, 169 (1998). Other dialkyl carbonates behave similarly.

For other reactions of dialkyl carbonates, see Diethyl­ carbonate, A12477.

Nale, D. B.; Bhanage, B. M. Copper-catalyzed efficient synthesis of a 2-benzimidazolone scaffold from 2-nitroaniline and dimethyl carbonate via a hydrosilylation reaction. Green Chem. 2015, 17 (4), 2480-2486.

Earle, M. J.; Noe, M.; Perosa, A.; Seddon, K. R. Improved synthesis of tadalafil using dimethyl carbonate and ionic liquids. RSC Adv. 2014, 4 (3), 1204-1211.

GHS Hazard and Precautionary Statements

Hazard Statements: H225

Highly flammable liquid and vapour.

Precautionary Statements: P210-P280-P240-P241-P233-P242-P243-P303+P361+P353-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Keep container tightly closed. Use only non-sparking tools. Take precautionary measures against static discharge. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,3241
Beilstein
635821
Hazard Class
3
Packing Group
II
Harmonized Tariff Code
2920.90
TSCA
Yes
RTECS
FG0450000

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