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5927-18-4 - Trimethyl phosphonoacetate, 98% - Dimethyl methoxycarbonylmethylphosphonate - Phosphonoacetic acid trimethyl ester - A13301 - Alfa Aesar

A13301 Trimethyl phosphonoacetate, 98%

Codice CAS
5927-18-4
Sinonimi
Dimethyl methoxycarbonylmethylphosphonate
Phosphonoacetic acid trimethyl ester

Dimensioni Prezzo ($) Quantità Disponibilità
25g 38,70
100g 107,00
500g 464,00
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Trimethyl phosphonoacetate, 98%

MDL
MFCD00008452
EINECS
227-663-0

Proprietà chimiche

Formula
C5H11O5P
Peso formula
182.11
Punto di ebollizione
119-120°/1mm
Punto di infiammabilità
70°(158°F)
Densità
1.263
Indice di rifrazione
1.4370
Solubilità
Slightly miscible with water.

Applicazioni

Trimethyl phosphonoacetate is used in the preparation of sarin A by intramolecular Mannich-type reactions. It is involved in the Horner-Wadsworth-Emmons olefination with aldehydes and ketones to give acrylic esters. It is also involved in oxa-Michael reactions, prenylation of oxindoles and heterocyclization reactions.

Note

Incompatible with strong oxidizing agents.

Letteratura

Horner-Wadsworth-Emmons olefination (see Appendix 1) with aldehydes and ketones gives acrylic esters, cf Triethyl­ phosphonoacetate, A14120. In general, the (E):(Z) ratio of the resulting alkene increases as the counter-ion becomes smaller (K, Na, Li) and as the temperature increases. See, e.g.: J. Org. Chem., 55, 3386 (1990). Reaction with ɑ-hydroxy ketones provides a simple route to butenolides: Tetrahedron Lett., 36, 2839 (1995):

Cheng, D.; Liu, Y.; Wang, H.; Weng, X.; Wu, Z. Enhanced CO2 adsorptive performance of PEI/SBA-15 adsorbent using phosphate ester based surfactants as additives. J. Environ. Sci. 2015, 38, 1-7.

Sugimoto, K.; Miyakawa, Y.; Tokuyama, H. Total synthesis of (-)-rhazinilam using 1, 3-dipolar cycloaddition of optically active münchnone intermediate. Tetrahedron 2015, 71 (22), 3619-3624.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H227-H315-H319-H335

Combustible liquid. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Dichiarazioni precauzionali: P210u-P261-P280a-P305+P351+P338-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
1865177
Codice tariffe armonizzato
2931.39
TSCA
Yes

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