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867-13-0 - Triethyl phosphonoacetate, 98+% - Diethyl ethoxycarbonylmethylphosphonate - Phosphonoacetic acid triethyl ester - A14120 - Alfa Aesar

A14120 Triethyl phosphonoacetate, 98+%

CAS Number
867-13-0
Synonyms
Diethyl ethoxycarbonylmethylphosphonate
Phosphonoacetic acid triethyl ester

Size Price ($) Quantity Availability
100g 72.27
500g 241.65
2500g 1038.24
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Triethyl phosphonoacetate, 98+%

MDL
MFCD00009177
EINECS
212-757-6

Chemical Properties

Formula
C8H17O5P
Formula Weight
224.19
Melting point
-24°
Boiling Point
260-262°
Flash Point
165°(329°F)
Density
1.125
Refractive Index
1.4310
Solubility
Slightly miscible with water.

Applications

Triethyl phosphonoacetate serves as a reactant used in Horner-Wadsworth-Emmons reactions, Tsuji-Trost type reactions, Intramolecular Heck-type cyclization and isomerizations and Intramolecular aryne-ene reactions. In Horner-Wadsworth-Emmons reaction, it is utilized as a reagent to prepare chiral 2-methylcyclopropanecarboxylic acid from (S)-propylene oxide.

Notes

Incompatible with strong oxidizing agents.

Literature References

Wadsworth-Emmons (Horner) reaction with aldehydes and ketones gives acrylic esters. See, e.g.: Org. Synth. Coll., 5, 509, 547 (1973), and Appendix 1.

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).

Kim, H.; Paik, Y. K. Synthesis of Photoaffinity-Labeled Daumone Analogs. Bull. Korean Chem. Soc. 2015, 36 (9), 2177-2178.

Lee, J. Y.; Choi, J. H.; Ryoo, K. S.; Kwon, Y. B.; Hong, Y. P. Economical Synthesis of Grapevine Moth Sex Pheromone. Bull. Korean Chem. Soc. 2015, 36 (1), 421-423.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319

Causes skin irritation. Causes serious eye irritation.

Precautionary Statements: P280-P264-P305+P351+P338-P362-P321-P332+P313-P337+P313-P302+P352

Wear protective gloves/protective clothing/eye protection/face protection. Wash thoroughly after handling. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Take off contaminated clothing and wash before reuse. Specific treatment (see label). If skin irritation occurs: Get medical advice/attention. If eye irritation persists: IF ON SKIN: Wash with plenty of soap and water.

Other References

Beilstein
1343714
Harmonized Tariff Code
2931.90
TSCA
Yes
RTECS
AG9800000

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