Triethylphosphonoacetat

Triethyl phosphonoacetate

HCID 13345CAS 867-13-0
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Grundinformationen

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 Struktureigenschaften

XLogP
0,5
Polarare Oberfläche (TPSA)
61,8 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
8
Schwere Atome
14

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Classes -> Organophosphates, Other
Food Contact Substances · 2 Einträge

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
165 °C · 165°C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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 · 4 Einträge

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
TSCA listed
ridadr
UN 3082 9/PG 3
hs_code
29310095
RTECS-Nr.
AG9800000
risk_code
51/53-36/37/38

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 · 2 Einträge

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.

Vor- und nachgelagerte Produkte

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上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
山东德信精细化工有限公司18553366272

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