ethyl 2-(diethyl phosphono)acetate

EN300-52552

Product class

Building Blocks

CAS number

867-13-0

MW

224.19

Purity

95%

Stock Availability

UA, DE, US, EU

Lead time

1-5 days delivery time

Reagent for Horner–Wadsworth–Emmons reaction

Triethyl phosphonoacetate is a reagent for Horner–Wadsworth–Emmons reaction[1]. It's a liquid that with proper storage conditions a shelf stable. Through deprotonation by diverse bases, it yields a carbanion capable of reacting with carbonyl compounds, resulting in alkene formation. Notably, the reaction showcases a preference for the E-isomer, although this selectivity tends to be less pronounced with ketones compared to aldehydes. In the case of sensitive substances, the Horner-Wadsworth-Emmons reaction (HWE) can be carried out under Masamune-Roush conditions. This entails utilizing LiCl and DBU in acetonitrile, allowing for the successful transformation of these substrates into desired products.

Synonyms: Acetic acid, (diethoxyphosphinyl)-, ethyl ester (9CI); Acetic acid, phosphono-, triethyl ester (6CI, 7CI, 8CI); (Diethoxyphosphinyl)acetic acid ethyl ester; (Diethoxyphosphoryl)acetic acid ethyl ester; (Ethoxycarbonylmethyl)diethoxyphosphine oxide,;2-(Diethoxyphosphinyl)acetic acid ethyl ester; 2-Phosphonoacetic acid triethyl ester; Carbethoxymethyldiethyl phosphonate; Diethyl 2-ethoxy-2-oxoethylphosphonate; Diethyl carbethoxymethylphosphonate; Diethyl ethoxycarbonylmethanephosphonate; Diethyl phosphonoacetic acid ethyl ester; Ethyl (diethoxyphosphinyl)acetate

1. Triethyl Phosphonoacetate.Abell A.; Bessières B. Encyclopedia of Reagents for Organic Synthesis 2006. DOI: 10.1002/047084289X.rt225.pub2

Name:

ethyl 2-(diethyl phosphono)acetate

SMILES:

CCOC(=O)CP(=O)(OCC)OCC

CAS number:

867-13-0

CLogP:

0.632

ACD number:

MFCD00009177

Dangerous good:

Yes

Class:

Lab Reagents, Esters

Formula:

C₈H₁₇O₅P

Subclass:

Esters

MW:

224.19

Product class:

Building Blocks