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

A13301 Trimethyl phosphonoacetate, 98%

CAS Number
5927-18-4
Synonyms
Dimethyl methoxycarbonylmethylphosphonate
Phosphonoacetic acid trimethyl ester

Size Price ($) Quantity Availability
25g 37.80
100g 109.18
500g 425.70
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Trimethyl phosphonoacetate, 98%

MDL
MFCD00008452
EINECS
227-663-0

Chemical Properties

Formula
C5H11O5P
Formula Weight
182.11
Boiling Point
119-120°/1mm
Flash Point
70°(158°F)
Density
1.263
Refractive Index
1.4370
Solubility
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.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335-H227

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

Precautionary Statements: 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.

Other References

Beilstein
1865177
Harmonized Tariff Code
2931.90
TSCA
Yes

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