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

A14120 Triethyl phosphonoacetate, 98+%

Codice CAS
867-13-0
Sinonimi
Diethyl ethoxycarbonylmethylphosphonate
Phosphonoacetic acid triethyl ester

Dimensioni Prezzo ($) Quantità Disponibilità
100g 73,90
500g 254,00
2500g 1028,00
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Triethyl phosphonoacetate, 98+%

MDL
MFCD00009177
EINECS
212-757-6

Proprietà chimiche

Formula
C8H17O5P
Peso formula
224.19
Punto di fusione
-24°
Punto di ebollizione
260-262°
Punto di infiammabilità
165°(329°F)
Densità
1.125
Indice di rifrazione
1.4310
Solubilità
Slightly miscible with water.

Applicazioni

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.

Note

Incompatible with strong oxidizing agents.

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H315-H319

Causes skin irritation. Causes serious eye irritation.

Dichiarazioni precauzionali: 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.

Altri riferimenti

Beilstein
1343714
Codice tariffe armonizzato
2931.90
TSCA
Yes
RTECS
AG9800000

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