Triethylphosphonoacetat
Triethyl phosphonoacetate
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Grundinformationen
- CAS
867-13-0- Standard-SMILES
CCOC(=O)CP(=O)(OCC)OCC- InChIKey
GGUBFICZYGKNTD-UHFFFAOYSA-N- Summenformel
- C8H17O5P
- Durchschnittliche Molmasse
- 224,19 g/mol
- Monoisotopische Masse
- 224,08136027
Namen und Bezeichner
- Bevorzugter Name
- Triethyl phosphonoacetate
- IUPAC
- ethyl 2-diethoxyphosphorylacetate
- Lokaler Name
- Triethylphosphonoacetat
- Englischer Name
- Triethyl phosphonoacetate
- Summenformel
- C8H17O5P
- Molmasse
- 224.19
Namen und Synonyme
Triethyl phosphonoacetate867-13-0Ethyl (diethoxyphosphoryl)acetateEthyl (diethylphosphono)acetateTriethyl phosphonoethanoateAcetic acid, (diethoxyphosphinyl)-, ethyl esterDiethyl carbethoxymethylphosphonateDiethyl ethoxycarbonylmethanephosphonateDiethyl carboethoxymethylphosphonateEthyl diethoxyphosphoryl acetateTL 465ETHYL (DIETHOXYPHOSPHINYL)ACETATE
Weitere Namen anzeigen
ETHYL 2-(DIETHOXYPHOSPHORYL)ACETATEETHYL DIETHYLPHOSPHONOACETATETriethyl phosphonacetateTicagrelor Impurity 150Triethyl phosphonoacetatCarbethoxyMethyldiethyl PhosphonateDIETHYLPHOSPHONOACETIC ACID ETHYL ESTERDIETHYL ETHOXYCARBONYLMETHYLPHOSPHONATEtl465
Phosphonoacetic acid, triethyl esterAcetic acid, phosphono-, triethyl esterDiethyl phosphonoacetic acid, ethyl esterAcetic acid, 2-(diethoxyphosphinyl)-, ethyl ester(Ethoxycarbonylmethyl)diethoxyphospshine oxideDTXSID4041573Acetic acid, diethylphosphono-, ethyl esterNSC-13898
Datenbank-Bezeichner
- CAS
867-13-0- PubChem CID
- 13345
- DTXSID
DTXSID4041573- ChEMBL
CHEMBL3185304- UNII
- 022826171T
- EC Number
- 212-757-6
- Nikkaji
- J54.207E
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 0,5
- Polarare Oberfläche (TPSA)
- 61,8 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 8
- Schwere Atome
- 14
- Formalladung
- 0
- Komplexität
- 206
Experimentelle und physikochemische Eigenschaften
Chemical ClassesOther Classes -> Organophosphates, Other
Food Contact Substances
FCS -> FDA Cumulative Estimated Daily Intake (CEDI)
FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical DescriptionClear light yellow liquid; [Acros Organics MSDS]
Collision Cross Section143.7 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID4041573]
Physikochemische Eigenschaften
- Schmelzpunkt
- -24 °C · -24°C
- Siedepunkt
- 142 · 142-145 °C9 mm Hg(lit.)
- Dichte
- 1.13 g/mL · 1.13 g/mL at 25 °C(lit.)
- Dampfdruck
- 0.61 Pa · 0.61Pa at 25℃
- Brechungsindex
- 20 · n20/D 1.431(lit.)
- Flammpunkt
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H315 (22.9%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 70 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
Chemical: Acetic acid, (diethoxyphosphinyl)-, ethyl ester
Regulation (EC) No 1935/2004 (amended)
Status: Active Update: 19-08-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/11013
Acetic acid, (diethoxyphosphinyl)-, ethyl ester: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazards SummaryOral lethal-dose (rat) > 500 mg/kg; [RTECS] An irritant that may cause serious eye injury; [Acros Organics MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (22.9%)
Toxikologische Informationen
Toxicity DataLCLo (mouse) = 1,180 mg/m3/10min
Sicherheitsdaten
- wgk
- 3
- tsca
Chemie und Industrie
Verwendung und Herstellung
UsesUsed to make large scale and fine chemicals, active pharmaceutical ingredients or fragrances, and to polymerize bottle grade PET; [ExPub: ECHA REACH Registrations]
General Manufacturing InformationAcetic acid, 2-(diethoxyphosphinyl)-, ethyl ester: ACTIVE
Anwendungen
BeschreibungTriethyl 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].
VerwendenTriethyl 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.
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