ethoxyethene

• ChemBase ID: 138621
• Molecular Formular: C4H8O
• Molecular Mass: 72.10572
• Monoisotopic Mass: 72.05751488
• SMILES: CCOC=C
• Canonical SMILES: CCOC=C
• InChI: InChI=1S/C4H8O/c1-3-5-4-2/h3H,1,4H2,2H3
• InChIKey: FJKIXWOMBXYWOQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 109-92-2
• EC Number: 203-718-4
• MDL Number: MFCD00009248
• Beilstein Number: 605351
• PubChem SID: 24866417; 162232873
• PubChem CID: 8023

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.9860318
• LogD (pH = 7.4): 0.9860318
• Log P: 0.9860318
• Molar Refractivity: 21.4533 cm^3
• Polarizability: 8.548852 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -115°C; -116 °C(lit.)
• Boiling Point: 33 °C(lit.); 33-34°C
• Flash Point: -45°C(-49°F); -46 °C; -50.8 °F
• Density: 0.753 g/mL at 25 °C(lit.); 0.754
• Refractive Index: 1.3765; n20/D 1.376; n20/D 1.376(lit.)

Safety Information

• RTECS: KO0710000
• European Hazard Symbols: Highly flammable (F+); Irritant (Xi)
• UN Number: 1302; UN1302
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 1; I
• Risk Statements: 12-19-36/37/38; 12-36/37-66-67
• Safety Statements: 3/7-16-23-26-33-36; 3/7-9-16-26-29-33
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H224-H319-H335-H336; H225-H315-H319-H335
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1302 3/PG 1
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (GC); ≥99%; 99%; 99%, stab.
• Grade: purum
• Contains: ~0.1% diethylaniline as stabilizer; 0.1% KOH as stabilizer; 0.1% potassium hydroxide as stabilizer; 0.1% triethanolamine as stabilizer
• Linear Formula: C2H5OCH=CH2

DETAILS

Sigma Aldrich - 422177

Packaging
1 L in glass bottle
250 mL in glass bottle

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).