Triethylphosphonoacetat

Bezeichnung:Triethylphosphonoacetat

CAS-Nr867-13-0

Englisch Name:Triethyl phosphonoacetate

CBNumberCB3487949

SummenformelC8H17O5P

Molgewicht224.19

MOL-Datei867-13-0.mol

Synonyma

Triethylphosphonoacetat

Triethylphosphonoacetat physikalisch-chemischer Eigenschaften

Schmelzpunkt	-24°C
Siedepunkt	142-145 °C9 mm Hg(lit.)
Dichte	1.13 g/mL at 25 °C(lit.)
Dampfdruck	0.61Pa at 25℃
Brechungsindex	n20/D 1.431(lit.)
Flammpunkt	165°C
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit	Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
Aggregatzustand	Liquid
Wichte	1.130
Farbe	Clear
Wasserlöslichkeit	Slightly miscible with water.
BRN	1343714
InChIKey	GGUBFICZYGKNTD-UHFFFAOYSA-N
LogP	1.13 at 30℃
CAS Datenbank	867-13-0(CAS DataBase Reference)
EPA chemische Informationen	Acetic acid, (diethoxyphosphinyl)-, ethyl ester (867-13-0)

Sicherheit

Kennzeichnung gefährlicher	N,Xi,Xn
R-Sätze:	51/53-36/37/38
S-Sätze:	61-37/39-26-36
RIDADR	UN 3082 9/PG 3
WGK Germany	3
RTECS-Nr.	AG9800000
Hazard Note	Harmful
TSCA	Yes
HazardClass	9
PackingGroup	III
HS Code	29310095

Gefahreninformationscode (GHS)

Triethyl phosphonoacetate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R51/53:Giftig für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
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].
Chemische Eigenschaften
Triethyl phosphonoacetate is Colorless to light yellow liqui
Verwenden
Triethyl phosphonoacetate is used for Horner-Emmons modification.
Verwenden
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.
läuterung methode
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.]
Einzelnachweise
[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 Upstream-Materialien And Downstream Produkte

Triethylphosphonoacetat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

867-13-0, Triethyl phosphonoacetate Verwandte Suche:

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