Триэтилфосфоноацетат
Триэтилфосфоноацетат атрибут
| Температура плавления: |
-24°C |
| Температура кипения: |
142-145 °C9 mm Hg(lit.) |
| плотность: |
1.13 g/mL at 25 °C(lit.) |
| давление пара: |
0.61Pa at 25℃ |
| показатель преломления: |
n20/D 1.431(lit.) |
| Fp: |
165°C |
| температура хранения: |
Keep in dark place,Sealed in dry,Room Temperature |
| растворимость: |
Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly) |
| форма: |
жидкость |
| Удельный вес: |
1.130 |
| цвет: |
Прозрачный |
| Вязкость: |
5.2mm2/s |
| Растворимость в воде: |
Slightly miscible with water. |
| БРН: |
1343714 |
| ИнЧИКей: |
GGUBFICZYGKNTD-UHFFFAOYSA-N |
| LogP: |
1.13 at 30℃ |
| Непрямые добавки, используемые в веществах, контактирующих с пищевыми продуктами: |
CARBETHOXYMETHYL DIETHYL PHOSPHONATE |
| Справочник по базе данных CAS: |
867-13-0(CAS DataBase Reference) |
| FDA UNII: |
022826171T |
| Система регистрации веществ EPA: |
Acetic acid, (diethoxyphosphinyl)-, ethyl ester (867-13-0) |
Триэтилфосфоноацетат химические свойства, назначение, производство
Описание
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].
Химические свойства
Triethyl phosphonoacetate is Colorless to light yellow liqui
Использование
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.
Методы очистки
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.]
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