Triethyl phosphonoacetate
- CAS No.
- 867-13-0
- Chemical Name:
- Triethyl phosphonoacetate
- Synonyms
- ETHYL 2-(DIETHOXYPHOSPHORYL)ACETATE;ETHYL DIETHYLPHOSPHONOACETATE;Triethyl phosphonacetate;Ticagrelor Impurity 150;Triethyl phosphonoacetat;CarbethoxyMethyldiethyl Phosphonate;DIETHYLPHOSPHONOACETIC ACID ETHYL ESTER;DIETHYL ETHOXYCARBONYLMETHYLPHOSPHONATE;tl465;NSC 13898
- CBNumber:
- CB3487949
- Molecular Formula:
- C8H17O5P
- Molecular Weight:
- 224.19
- MDL Number:
- MFCD00009177
- MOL File:
- 867-13-0.mol
- MSDS File:
- SDS
| 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 |
n |
| 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 |
| Specific Gravity | 1.130 |
| color | Clear |
| Viscosity | 5.2mm2/s |
| Water Solubility | Slightly miscible with water. |
| BRN | 1343714 |
| InChIKey | GGUBFICZYGKNTD-UHFFFAOYSA-N |
| LogP | 1.13 at 30℃ |
| Indirect Additives used in Food Contact Substances | CARBETHOXYMETHYL DIETHYL PHOSPHONATE |
| CAS DataBase Reference | 867-13-0(CAS DataBase Reference) |
| FDA UNII | 022826171T |
| EPA Substance Registry System | Acetic acid, (diethoxyphosphinyl)-, ethyl ester (867-13-0) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS07,GHS09 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H319-H411 | |||||||||
| Precautionary statements | P264-P273-P280-P305+P351+P338-P337+P313-P391 | |||||||||
| 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 | |||||||||
| NFPA 704 |
|
Triethyl phosphonoacetate price More Price(43)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | 79525 | Triethyl phosphonoacetate purum, ≥97.0% (GC) | 867-13-0 | 100ml | $107 | 2024-03-01 | Buy |
| Sigma-Aldrich | 79525 | Triethyl phosphonoacetate purum, ≥97.0% (GC) | 867-13-0 | 500ml | $397 | 2024-03-01 | Buy |
| TCI Chemical | D1523 | Triethyl Phosphonoacetate >97.0%(GC) | 867-13-0 | 25g | $29 | 2024-03-01 | Buy |
| TCI Chemical | D1523 | Triethyl Phosphonoacetate >97.0%(GC) | 867-13-0 | 100g | $63 | 2024-03-01 | Buy |
| Alfa Aesar | A14120 | Triethyl phosphonoacetate, 98+% | 867-13-0 | 100g | $90.4 | 2024-03-01 | Buy |
Triethyl phosphonoacetate Chemical Properties,Uses,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.
Triethyl phosphonoacetate Preparation Products And Raw materials
Raw materials
Preparation Products
1of4
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Jiangxi Sunway Chemical Co., Ltd. | +86-0794-5259909 +8615888611133 | dave@jxswchem.com | China | 22 | 58 |
| Jiangxi Sunway Chemical Co., Ltd. | +86-0794-5259909 +8615888611133 | dave@jxswchem.com | China | 22 | 58 |
| Hebei Mojin Biotechnology Co., Ltd | +86 13288715578 +8613288715578 | sales@hbmojin.com | China | 12837 | 58 |
| Hebei Yanxi Chemical Co., Ltd. | +8617531190177 | peter@yan-xi.com | China | 5858 | 58 |
| Hebei Weibang Biotechnology Co., Ltd | +8617732866630 | bess@weibangbio.com | China | 18186 | 58 |
| Henan Fengda Chemical Co., Ltd | +86-371-86557731 +86-13613820652 | info@fdachem.com | China | 20288 | 58 |
| Capot Chemical Co.,Ltd. | +86-（0）57185586718 +86-13336195806 | sales@capot.com | China | 29791 | 60 |
| Shanghai Daken Advanced Materials Co.,Ltd | +86-371-66670886 | info@dakenam.com | China | 18644 | 58 |
| Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | info@tianfuchem.com | China | 21639 | 55 |
| Hangzhou FandaChem Co.,Ltd. | +8615858145714 | FandaChem@Gmail.com | China | 9220 | 55 |
View Lastest Price from Triethyl phosphonoacetate manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2024-11-04 | Triethyl phosphonoacetate
867-13-0
|
US $0.00 / KG | 1KG | 98%min | 30tons/month | WUHAN FORTUNA CHEMICAL CO., LTD | |
 |
2024-10-31 | Triethyl phosphonoacetate
867-13-0
|
US $0.00-0.00 / KG | 1KG | 99% | 500000kg | Hebei Weibang Biotechnology Co., Ltd | |
 |
2024-10-25 | Triethyl phosphonoacetate
867-13-0
|
US $30.00-7.00 / kg | 1kg | 0.99 | 20 tons | Hebei Yanxi Chemical Co., Ltd. |
-
- Triethyl phosphonoacetate
867-13-0
- US $0.00 / KG
- 98%min
- WUHAN FORTUNA CHEMICAL CO., LTD
-
- Triethyl phosphonoacetate
867-13-0
- US $0.00-0.00 / KG
- 99%
- Hebei Weibang Biotechnology Co., Ltd
-
- Triethyl phosphonoacetate
867-13-0
- US $30.00-7.00 / kg
- 0.99
- Hebei Yanxi Chemical Co., Ltd.