| Identification | More | [Name]
Triethyl phosphonoacetate | [CAS]
867-13-0 | [Synonyms]
AURORA KA-1452
DIETHYL ETHOXYCARBONYLMETHANEPHOSPHONATE
DIETHYL ETHOXYCARBONYLMETHYLPHOSPHONATE
DIETHYLPHOSPHONOACETIC ACID ETHYL ESTER
ETHOXYCARBONYLMETHANEPHOSPHONIC ACID DIETHYL ESTER
ETHYL 2-(DIETHOXYPHOSPHORYL)ACETATE
ETHYL DIETHYLPHOSPHONOACETATE
O,O-DIETHYL ETHOXYCARBONYLMETHYL PHOSPHONATE
PHOSPHONOACETIC ACID TRIETHYL ESTER
TRIETHYL CARBOXYMETHYLPHOSPHONATE
TRIETHYL PHOSPHONOACETATE
TRIETHYL PHOSPHONOACTETATE
(diethoxyphosphinyl)-aceticaciethylester
Aceticacid,(diethoxyphosphinyl)-,ethylester
diethylphosphono-aceticaciethylester
ethyl(diethoxyphosphinyl)acetate
Ethyl(diethyoxyphosphoryl)acetate
ethyldiethoxyphosphorylacetate
phosphono-aceticacitriethylester
tl465 | [EINECS(EC#)]
212-757-6 | [Molecular Formula]
C8H17O5P | [MDL Number]
MFCD00009177 | [Molecular Weight]
224.19 | [MOL File]
867-13-0.mol |
| Chemical Properties | Back Directory | [Appearance]
Colorless to light yellow liqui | [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 | [color ]
Clear | [Specific Gravity]
1.130 | [Water Solubility ]
Slightly miscible with water. | [Detection Methods]
GC,NMR | [BRN ]
1343714 | [InChIKey]
GGUBFICZYGKNTD-UHFFFAOYSA-N | [LogP]
1.13 at 30℃ | [CAS DataBase Reference]
867-13-0(CAS DataBase Reference) | [EPA Substance Registry System]
867-13-0(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
N,Xi,Xn | [Risk Statements ]
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 3082 9/PG 3
| [WGK Germany ]
3
| [RTECS ]
AG9800000
| [Hazard Note ]
Harmful | [TSCA ]
Yes | [HazardClass ]
9 | [PackingGroup ]
III | [HS Code ]
29310095 |
| Hazard Information | Back Directory | [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.
| [reaction suitability]
reaction type: C-C Bond Formation | [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. |
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