Ethoxyacetylene

• Catalog No.: A14245
• CAS Number: 927-80-0
• M. F.: C4H6O
• M. W.: 70.08984
• Purity: ca 50% w/w in hexanes

SYNONYMS

• Title: 乙氧基乙炔
• IUPAC name: ethoxyethyne
• IUPAC Traditional name: ethoxy-ethyne
• Synonyms: Ethyl ethynyl ether

DATABASE IDS

• Beilstein Number: 741882
• EC Number: 213-164-5
• MDL Number: MFCD00009247
• CAS Number: 927-80-0

PROPERTIES

• Purity: ca 50% w/w in hexanes
• Boiling Point: 55-56°C
• Density: 0.718
• Flash Point: -28°C(-18°F)
• Refractive Index: 1.3800
• GHS Hazard statements: H225-H304-H361-H373-H315-H303-H401-H411
• European Hazard Symbols: X
• European Hazard Symbols: Flammable (F)
• European Hazard Symbols: Nature polluting (N)
• GHS Precautionary statements: P210-P280H-P281-P301+P330+P331-P315-P403+P235
• Risk Statements: 11-38-48/20-62-51/53-65
• RTECS: KN9900000
• Safety Statements: 9-16-29-33-36/37-61-62
• TSCA Listed: 否
• Hazard Class: 3
• UN Number: UN1993
• Packing Group: II

REFERENCES

• Supplied in solution to reduce polymerization. Quantities offered relate to gross weight of solution.
• Undergoes [2+2] cycloaddition reactions with ketenes to give cyclobutenone derivatives: J. Org. Chem., 38, 1451 (1973).
• Adds to carbonyl compounds in the presence of ZnBr₂: Can. J. Chem., 54, 2310 (1976).
• The Grignard reagent, prepared by exchange with ethyl magnesium bromide, adds to carbonyl compounds to give carbinols which rearrange in acid to ɑ?-unsaturated acids. Alternatively, partial reduction of the adduct followed by hydrolysis provides a route to ɑ?-unsaturated aldehydes: J. Chem. Soc., 1823 (1949); Rec. Trav. Chim., 82, 305 (1963):
  
• Rearrangement by BF₃ etherate leads directly to the ethyl ester: Rec. Trav. Chim., 78, 664 (1959); Chem. Lett., 1129 (1981); 241, 1271 (1982). See also Chloroacetaldehyde diethyl acetal, L07661.
• Has been used as a mild dehydrating agent in peptide synthesis: Rec. Trav. Chim., 77, 1153 (1958), and for conversion of sensitive dicarboxylic acids to their anhydrides: J. Org. Chem., 33, 3808 (1968).