- Triethylphosphonoacetat
-
- $8.00 / 1KG
-
2024-01-22
- CAS:867-13-0
- Min. Order: 1KG
- Purity: 99%
- Supply Ability: g-kg-tons, free sample is available
|
| | Triethyl phosphonoacetate Basic information |
| | Triethyl phosphonoacetate Chemical Properties |
| 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.) | | Fp | 165°C | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly) | | form | Liquid | | Specific Gravity | 1.130 | | color | Clear | | 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) |
| 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 |
| | Triethyl phosphonoacetate Usage And Synthesis |
| 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. |
| | Triethyl phosphonoacetate Preparation Products And Raw materials |
|