Triethyl phosphonoacetate Property

Melting point:

-24°C

Boiling point:

142-145 °C9 mm Hg(lit.)

Density 

1.13 g/mL at 25 °C(lit.)

vapor pressure 

0.61Pa at 25℃

refractive index 

n20/D 1.431(lit.)

Flash point:

165°C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Liquid

color 

Clear

Specific Gravity

1.130

Water Solubility 

Slightly miscible with water.

BRN 

1343714

InChIKey

GGUBFICZYGKNTD-UHFFFAOYSA-N

LogP

1.13 at 30℃

CAS DataBase Reference

867-13-0(CAS DataBase Reference)

EPA Substance Registry System

Acetic acid, (diethoxyphosphinyl)-, ethyl ester (867-13-0)

Safety

Hazard Codes 

N,Xi,Xn

Risk Statements 

51/53-36/37/38

Safety Statements 

61-37/39-26-36

RIDADR 

UN 3082 9/PG 3

WGK Germany 

3

RTECS 

AG9800000

Hazard Note 

Harmful

TSCA 

Yes

HazardClass 

9

PackingGroup 

III

HS Code 

29310095

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H319Causes serious eye irritation

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

P391Collect spillage. Hazardous to the aquatic environment

Triethyl phosphonoacetate Chemical Properties,Usage,Production

Description

Triethyl phosphonoacetate is a reagent for organic synthesis used in the Horner-Wadsworth-Emmons reaction (HWE) or the Horner-Emmons modification. This compound 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. It can synthesize β-Keto Phosphonates via an acylation reaction of triethyl phosphonoacetate with carboxylic acid chlorides in the presence of magnesium chloride-triethylamine followed by decarbethoxylation. Acylation of triethyl phosphonoacetate using magnesium ethoxide affords acyl phosphonoacetates, which, on treatment with catalytic p-TsOH in water, are converted into 2-aryl-2-oxoalkylphosphonates[1-2].

Chemical Properties

Triethyl phosphonoacetate is Colorless to light yellow liqui

Uses

Triethyl phosphonoacetate is used for Horner-Emmons modification.

Uses

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.

Purification Methods

Purify it by fractional distillation, preferably in vacuo. NMR has P resonance at 19.5 relative to orthophosphate. [Kosolapoff & Powell J Am Chem Soc 68 1103 1946, Kosolapoff & Powell J Am Chem Soc 72 4198 1950, Speziale & Freeman J Org Chem 23 1586 1958, Beilstein 4 IV 3613.]

References

[1] D. Kim, D. Rhie, M. S. Kong. “A New Synthesis of 2-Aryl-2-Oxoalkylphosphonates from Triethyl Phosphonoacetate.” Synthetic Communications 25 1 (1995): 2865–2869.
[2] D. Kim, T. Kim, M. S. Kong. “A Practical Synthesis of β-Keto Phosphonates from Triethyl Phosphonoacetate.” Synthetic Communications 32 1 (1996): 2487–2496.