Trimethyl phosphonoacetate, 98%
Trimethyl phosphonoacetate, 98%
Trimethyl phosphonoacetate, 98%
Thermo Scientific Chemicals

Trimethyl phosphonoacetate, 98%

CAS: 5927-18-4 | C5H11O5P | 182.112 g/mol
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Catalog number A13301.36
also known as A13301-36
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500 g
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Price (USD)
499.65
Online Exclusive
555.00
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Each
Chemical Identifiers
CAS5927-18-4
IUPAC Namemethyl 2-(dimethoxyphosphoryl)acetate
Molecular FormulaC5H11O5P
InChI KeySIGOIUCRXKUEIG-UHFFFAOYSA-N
SMILESCOC(=O)CP(=O)(OC)OC
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SpecificationsSpecification SheetSpecification Sheet
Appearance (Color)Clear, colourless
Assay (GC)>97.5%
Refractive Index1.4350-1.4390 @ 20*C
Formliquid
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.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

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.

Solubility
Slightly miscible with water.

Notes
Incompatible with strong oxidizing agents.
RUO – Research Use Only

General References:

  1. 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):
  2. 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.
  3. 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.