Triethyl phosphonoacetate

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| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 402321909

| ImageFile =Triethylphosphonoacetate.png

| ImageSize =

| PIN =Ethyl (diethoxyphosphoryl)acetate

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo =867-13-0

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 022826171T

| PubChem =13345

| SMILES =CCOC(=O)CP(=O)(OCC)OCC

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 12776

| InChI = 1/C8H17O5P/c1-4-11-8(9)7-14(10,12-5-2)13-6-3/h4-7H2,1-3H3

| InChIKey = GGUBFICZYGKNTD-UHFFFAOYAB

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C8H17O5P/c1-4-11-8(9)7-14(10,12-5-2)13-6-3/h4-7H2,1-3H3

| InChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = GGUBFICZYGKNTD-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| Formula =C₈H₁₇O₅P

| MolarMass =224.19 g/mol

| Appearance =

| Density =

| MeltingPt =

| BoilingPtC = 142 to 145

| BoilingPt_notes = at 9 mmHg

| Solubility =

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|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

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Triethyl phosphonoacetate is a reagent for organic synthesis used in the Horner-Wadsworth-Emmons reaction (HWE) or the Horner-Emmons modification.

Triethyl phosphonoacetate can be added dropwise to sodium methoxide solution to prepare a phosphonate anion. It has an acidic proton that can easily be abstracted by a weak base. When used in an HWE reaction with a carbonyl the resulting alkene formed is usually the E alkene, and is generated with excellent regioselectivity.{{cite journal|last1=Rathke|first1=Michael W.|last2=Nowak|first2=Michael|title=The Horner-Wadsworth-Emmons modification of the Wittig reaction using triethylamine and lithium or magnesium salts|journal=The Journal of Organic Chemistry|date=July 1985|volume=50|issue=15|pages=2624–2626|doi=10.1021/jo00215a004}}