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????????????????? ??? ???
?? ??:
867-13-0
???:
?????????????????
???(??):
?????????????????;????? ?????????
???:
Triethyl phosphonoacetate
???(??):
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
???:
C8H17O5P
??? ??:
224.19
MOL ??:
867-13-0.mol
MSDS ??:
SDS

????????????????? ??

???
-24°C
?? ?
142-145 °C9 mm Hg(lit.)
??
1.13 g/mL at 25 °C(lit.)
???
0.61Pa at 25℃
???
n20/D 1.431(lit.)
???
165°C
?? ??
Keep in dark place,Sealed in dry,Room Temperature
???
?????(?? ???), ???????(?? ???), ???(?? ???)
???
?????(??), ???????(??), ???(??)? ???
??? ??
??
Specific Gravity
1.130
??
???
???
?? ?? ??.
BRN
1343714
InChIKey
GGUBFICZYGKNTD-UHFFFAOYSA-N
LogP
1.13 at 30℃
CAS ??????
867-13-0(CAS DataBase Reference)
EPA
Acetic acid, (diethoxyphosphinyl)-, ethyl ester (867-13-0)
??
  • ?? ? ?? ??
  • ?? ? ???? ?? (GHS)
??? ?? N,Xi,Xn
?? ???? ?? 51/53-36/37/38
????? 61-37/39-26-36
????(UN No.) UN 3082 9/PG 3
WGK ?? 3
RTECS ?? AG9800000
?? ?? ?? Harmful
TSCA Yes
?? ?? 9
???? III
HS ?? 29310095
???? ?? 2000-3-1636
????(GHS): GHS hazard pictogramsGHS hazard pictograms
?? ?: Warning
??·?? ??:
?? ??·?? ?? ?? ?? ?? ?? ? ?? ?? P- ??
H319 ?? ?? ??? ??? ?? ? ?? ?? ??? ?? ?? 2A ?? GHS hazard pictograms P264, P280, P305+P351+P338,P337+P313P
H411 ??? ??? ?? ????? ??? ?? ????? ?? - ?? ?? 2
??????:
P264 ?? ??? ?? ??? ????.
P264 ?? ??? ?? ??? ????.
P273 ???? ???? ???.
P280 ????/???/???/?????? ?????.
P305+P351+P338 ?? ??? ? ?? ?? ???? ????. ???? ?????? ?????. ?? ????.
P337+P313 ?? ?? ??? ???? ???? ??· ??? ????.
P391 ???? ????.
NFPA 704
0
2 0

????????????????? MSDS


Triethyl phosphonoacetate

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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].

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Triethyl phosphonoacetate is Colorless to light yellow liqui

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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.]

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