Ethyl vinyl ether

• Catalog No.: A15691
• CAS Number: 109-92-2
• M. F.: C4H8O
• M. W.: 72.10572
• Purity: 99%, stab.

SYNONYMS

• Title: 乙烯基乙醚
• IUPAC name: ethoxyethene
• IUPAC Traditional name: ethyl vinyl ether
• Synonyms: Vinyl ethyl ether; Ethoxyethylene

DATABASE IDS

• CAS Number: 109-92-2
• Beilstein Number: 605351
• MDL Number: MFCD00009248
• EC Number: 203-718-4

PROPERTIES

• Purity: 99%, stab.
• Boiling Point: 33-34°C
• Density: 0.754
• Flash Point: -45°C(-49°F)
• Melting Point: -115°C
• Refractive Index: 1.3765
• GHS Hazard statements: H224-H319-H335-H336
• European Hazard Symbols: Irritant (Xi)
• European Hazard Symbols: Highly flammable (F+)
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 12-36/37-66-67
• RTECS: KO0710000
• Safety Statements: 3/7-9-16-26-29-33
• TSCA Listed: 是
• Hazard Class: 3
• UN Number: UN1302
• Packing Group: I

REFERENCES

• Also used in the protection of phenols as EE ethers which can be cleaved by acid-catalyzed methanolysis: J. Am. Chem. Soc., 119, 8071 (1997).
• Acid-catalyzed reaction with alcohols gives 1-ethoxyethyl (EE) ethers, useful as protected derivatives, e.g. in reactions with organometallics. Possible catalysts include: tosic acid: J. Am. Chem. Soc., 101, 7104 (1979); Org. Synth., 76, 199 (1998), PPTS: Tetrahedron Lett., 28, 4303 (1987), or dichloroacetic acid: J. Org. Chem., 37, 1947 (1972). Cleavage of this mixed acetal occurs in dilute acid, more readily than THP ether (see 3,4-Dihydro-2H-pyran, L02731). Protection of cyanohydrins allows use as acyl anion equivalents: Org. Synth. Coll., 7, 381 (1990):
  
• In the presence of Montmorillonite K10, an addition reaction with diethyl acetals gives the ?-ethoxy acetal of the bis-homologated aldehyde, providing, on acid cleavage, an effective route to the corresponding ɑ?-unsaturated aldehyde: Synthesis, 137 (1981).