dimethyl carbonate

• ChemBase ID: 109018
• Molecular Formular: C3H6O3
• Molecular Mass: 90.07794
• Monoisotopic Mass: 90.03169405
• SMILES: COC(=O)OC
• Canonical SMILES: COC(=O)OC
• InChI: InChI=1S/C3H6O3/c1-5-3(4)6-2/h1-2H3
• InChIKey: IEJIGPNLZYLLBP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dimethyl carbonate
• IUPAC Traditional name: dimethyl carbonate
• Synonyms: DIMETHYL CARBONATE; DMC; Methyl carbonate; Carbonic acid, dimethyl ester; Dimethyl carbonate; Carbonic acid dimethyl ester; 碳酸二甲酯

Database IDs

• CAS Number: 616-38-6
• EC Number: 210-478-4
• MDL Number: MFCD00008420
• Beilstein Number: 635821
• Merck Index: 143241
• PubChem SID: 24893471; 24873943; 162096129
• PubChem CID: 12021
• CHEBI ID: 36596
• Chemspider ID: 11526
• Wikipedia Title: Dimethyl_carbonate

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.5418395
• LogD (pH = 7.4): 0.5418395
• Log P: 0.5418395
• Molar Refractivity: 19.0364 cm^3
• Polarizability: 7.834368 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 13.9 g/100 mL in water; Insoluble in water. Miscible with alcohol, ether
• Apperance: APHA: <50; Clear liquid
• Melting Point: 2 - 4°C; 2-4 °C(lit.); ca 4°C
• Boiling Point: 90 °C(lit.); 90°C; 90°C
• Flash Point: 16 °C; 16°C(61°F); 60.8 °F
• Density: 1.069 g/mL at 25 °C(lit.); 1.069-1.073 g/mL; 1.070
• Refractive Index: 1.3680; n20/D 1.368(lit.); n20/D 1.369
• Vapor Pressure: 18 mmHg ( 21.1 °C)
• Vapor Density: 3.1 (vs air)

Safety Information

• Storage Warning: Moisture Sensitive
• RTECS: FG0450000
• European Hazard Symbols: Flammable (F)
• UN Number: 1161; UN1161
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11; R:11
• Safety Statements: 9-16; S:9-16
• TSCA Listed: 是
• GHS Pictograms: GHS02
• GHS Signal Word: Danger
• Main Hazard: Flammable
• GHS Hazard statements: H225
• GHS Precautionary statements: P210; P210-P241-P280-P303+P361+P353-P403+P235-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1161 3/PG 2

Product Information

• Purity: ≥99%; ≥99.0% (GC); 95+%; 99%
• Grade: anhydrous; purum; ReagentPlus®
• Impurities: <0.002% water; <0.005% water(100mL pkg)
• Linear Formula: (CH3O)2CO

DETAILS

MP Biomedicals - 05209547

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 517127

Packaging
1, 2 L in Sure/Seal™
100 mL in Sure/Seal™

Sigma Aldrich - D152927

Packaging
100, 500 g in glass bottle
19 kg in VerSA-Flow™
2.5 kg in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

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 180-220^o (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.