ethoxyethyne

• ChemBase ID: 89254
• Molecular Formular: C4H6O
• Molecular Mass: 70.08984
• Monoisotopic Mass: 70.04186481
• SMILES: O(CC)C#C
• Canonical SMILES: CCOC#C
• InChI: InChI=1S/C4H6O/c1-3-5-4-2/h1H,4H2,2H3
• InChIKey: WMYNMYVRWWCRPS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethoxyethyne
• IUPAC Traditional name: ethoxy-ethyne
• Synonyms: Ethyl ethynyl ether; Ethoxyacetylene, 50% hexane solution; ETHOXYETHYNE; Ethoxyacetylene solution; ETHOXYACETYLENE; Ethoxyacetylene; 乙氧基乙炔 溶液; 乙氧基乙炔

Database IDs

• CAS Number: 927-80-0
• EC Number: 213-164-5
• MDL Number: MFCD00009247
• Beilstein Number: 741882
• PubChem SID: 162076136; 24856434; 24845309
• PubChem CID: 61239

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.6464
• LogD (pH = 7.4): 0.6464
• Log P: 0.6464
• Molar Refractivity: 19.0474 cm^3
• Polarizability: 7.6914005 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 55-56°C
• Flash Point: -20.2 °F; -28°C(-18°F); -29 °C; -7°C
• Density: 0.718; 0.720 g/mL at 20 °C; 0.732 g/mL at 25 °C
• Refractive Index: 1.3800; n20/D 1.378; n20/D 1.379

Safety Information

• Storage Warning: Highly Flammable/Keep Cold
• RTECS: KN9900000
• European Hazard Symbols: Flammable (F); Nature polluting (N); X; Harmful (Xn)
• UN Number: 1993; UN1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-38-48/20-51/53-62-65-67; 11-38-48/20-62-51/53-65; 38-48/20-51/53-62-65-67
• Safety Statements: 16-36/37-61-62; 36/37-61-62; 9-16-29-33-36/37-61-62
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS07; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H304-H315-H336-H361-H373-H411; H225-H304-H361-H373-H315-H303-H401-H411; H304-H315-H336-H361-H373-H411
• GHS Precautionary statements: P210-P261-P273-P281-P301 + P310-P331; P210-P280H-P281-P301+P330+P331-P315-P403+P235; P261-P273-P281-P301 + P310-P331
• RID/ADR: UN 1993 3/PG 2
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ca 50% w/w in hexanes
• Concentration: ~40 wt. % in hexanes; ~40% in hexane
• Grade: technical
• Linear Formula: C2H5OC≡CH

DETAILS

MP Biomedicals - 05212038

MP Biomedicals Rare Chemical collection

MP Biomedicals - 05214288

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 271365

Application
Used with N-vinylamides and triflic anhydride in a direct, three-component synthesis of pyridines.1 Also used to prepare α,β-unsaturated esters from ketones via a Meyer-Schuster rearrangement.2
Packaging
1, 5 g in glass bottle

Sigma Aldrich - 02520

Other Notes
Lithiation and alkylation gives ethoxyalkynes, electron-rich alkynes, useful for [2+2] cycloadditions1,2,3,4

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).