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A14120 Triethyl phosphonoacetate, 98+%

CAS Number
867-13-0
Synonyms
Diethyl ethoxycarbonylmethylphosphonate
Phosphonoacetic acid triethyl ester

Stock No. Size Price ($) Quantity Availability
A14120-22 100g 76.80
A14120-36 500g 264.00
A14120-0E 2500g 1049.00
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Triethyl phosphonoacetate, 98+%

MDL
MFCD00009177
EINECS
212-757-6

Chemical Properties

Formula
C8H17O5P
Formula Weight
224.19
Melting point
-24°
Boiling Point
260-262°
Flash Point
165°(329°F)
Density
1.125
Refractive Index
1.4310
Storage & Sensitivity
Ambient temperatures.
Solubility
Slightly miscible with water.

Applications

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.

Notes

Incompatible with strong oxidizing agents.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H318-H335

Causes skin irritation. Causes serious eye damage. May cause respiratory irritation.

Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P312-P332+P313-P362-P501c

Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
1343714
Harmonized Tariff Code
2931.39
TSCA
Yes
RTECS
AG9800000

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