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

A13301 Trimethyl phosphonoacetate, 98%

Numéro CAS
5927-18-4
Synonymes
Dimethyl methoxycarbonylmethylphosphonate
Phosphonoacetic acid trimethyl ester

Dimensions Prix ($) Quantité Disponibilité
25g 37,80
100g 109,18
500g 425,70
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Trimethyl phosphonoacetate, 98%

MDL
MFCD00008452
EINECS
227-663-0

Propriétés chimiques

Formule
C5H11O5P
Poids formulaire
182.11
Point d'ébullition
119-120°/1mm
Point d'éclair
70°(158°F)
Densité
1.263
Indice de réfraction
1.4370
Solubilité
Slightly miscible with water.

Applications

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.

Notes

Incompatible with strong oxidizing agents.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H315-H319-H335-H227

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

Mentions de prudence: P210-P261-P280-P305+P351+P338-P304+P340-P362-P312-P405-P403+P233-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
1865177
Code tarifaire harmonisé
2931.90
TSCA
Yes

Recommandé

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Catalyseurs

Analytique et matériel de laboratoire