Triethyl phosphonoacetate

• Catalog No.: A14120
• CAS Number: 867-13-0
• M. F.: C8H17O5P
• M. W.: 224.191341
• Purity: 98+%

SYNONYMS

• Title: 膦酰乙酸三乙酯
• IUPAC name: ethyl 2-(diethoxyphosphoryl)acetate
• IUPAC Traditional name: triethyl phosphonoacetate
• Synonyms: Diethyl ethoxycarbonylmethylphosphonate; Phosphonoacetic acid triethyl ester

DATABASE IDS

• Beilstein Number: 1343714
• EC Number: 212-757-6
• MDL Number: MFCD00009177
• CAS Number: 867-13-0

PROPERTIES

• Purity: 98+%
• Boiling Point: 260-262°C
• Density: 1.125
• Flash Point: 165°C(329°F)
• Melting Point: -24°C
• Refractive Index: 1.4310
• GHS Hazard statements: H315-H319
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P280-P305+P351+P338-P302+P352-P321-P362-P332+P313
• Risk Statements: 36/38
• RTECS: AG9800000
• Safety Statements: 23-26-37
• TSCA Listed: 是

REFERENCES

• Base-catalyzed aldol, Cannizzaro and saponification reactions can be minimized, by the use of, e.g.: K₂CO₃: Synthesis, 300 (1983); Tetrahedron Lett., 26, 53 (1985); F^-: Tetrahedron Lett., 21, 2161 (1980); N-ethyldiisopropylamine + LiCl: Tetrahedron Lett., 25, 2183 (1984); Et₃N + Li halides: J. Org. Chem., 50, 2624 (1985).
• Reaction with aqueous formaldehyde does not lead to the "expected" Wadsworth-Emmons product, but to ethyl ɑ-(hydroxymethyl)acrylate, a precursor of the synthetically useful ethyl ɑ-bromomethylacrylate, by condensation with the initially-formed "aldol" product: Org. Synth. Coll., 8, 265 (1993).
• Wadsworth-Emmons (Horner) reaction with aldehydes and ketones gives acrylic esters. See, e.g.: Org. Synth. Coll., 5, 509, 547 (1973), and Appendix 1.