Triethyl phosphonoacetate
- Product Name
- 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
- Formula Weight
- 224.19
- MOL File
- 867-13-0.mol
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
- 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)
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
N-Bromosuccinimide Price
- Product number
- 79525
- Product name
- Triethyl phosphonoacetate
- Purity
- purum, ≥97.0% (GC)
- Packaging
- 100ml
- Price
- $110
- Updated
- 2025/07/31
- Product number
- 79525
- Product name
- Triethyl phosphonoacetate
- Purity
- purum, ≥97.0% (GC)
- Packaging
- 500ml
- Price
- $409
- Updated
- 2025/07/31
- Product number
- D1523
- Product name
- Triethyl Phosphonoacetate
- Purity
- >97.0%(GC)
- Packaging
- 25g
- Price
- $28
- Updated
- 2025/07/31
- Product number
- D1523
- Product name
- Triethyl Phosphonoacetate
- Purity
- >97.0%(GC)
- Packaging
- 100g
- Price
- $60
- Updated
- 2025/07/31
- Product number
- 15-7595
- Product name
- Triethyl phosphonoacetate, min. 98%, ALBRITECT PM-1
- Packaging
- 100g
- Price
- $53
- Updated
- 2021/12/16
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.
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.
Triethyl phosphonoacetate Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Triethyl phosphonoacetate manufacturers
- Product
- Triethyl phosphonoacetate 867-13-0
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 98%min
- Supply Ability
- 30tons/month
- Release date
- 2023-01-09
- Product
- Triethyl phosphonoacetate 867-13-0
- Price
- US $10.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 10 mt
- Release date
- 2025-03-13
- Product
- Triethyl phosphonoacetate 867-13-0
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 500000kg
- Release date
- 2024-10-31