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Triethyl phosphonoacetate

CAS No.867-13-0
Chemical Name:Triethyl phosphonoacetate
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
color Clear
Specific Gravity 1.130
Viscosity 5.2mm2/s
Water Solubility Slightly miscible with water.
BRN 1343714
InChIKey GGUBFICZYGKNTD-UHFFFAOYSA-N
LogP 1.13 at 30℃
Indirect Additives used in Food Contact Substances CARBETHOXYMETHYL DIETHYL PHOSPHONATE
CAS DataBase Reference 867-13-0(CAS DataBase Reference)
FDA UNII 022826171T
EPA Substance Registry System Acetic acid, (diethoxyphosphinyl)-, ethyl ester (867-13-0)
UNSPSC Code 12352108
NACRES NA.22

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

NFPA 704:

	0
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H319-H411
Precautionary statements P264-P273-P280-P305+P351+P338-P337+P313-P391

Triethyl phosphonoacetate Price More Price(10)

Brand: Sigma-Aldrich(India)
Product number: T61301
Product name : Triethyl phosphonoacetate
Purity: 98%
Packaging: 25G
Price: ₹2040
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: T61301
Product name : Triethyl phosphonoacetate
Purity: 98%
Packaging: 100G
Price: ₹5810
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 79525
Product name : Triethyl phosphonoacetate
Purity: purum, ≥97.0% (GC)
Packaging: 100ML
Price: ₹3052.65
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 79525
Product name : Triethyl phosphonoacetate
Purity: purum, ≥97.0% (GC)
Packaging: 500ML
Price: ₹11734.3
Updated: 2022/06/14
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Brand: TCI Chemicals (India)
Product number: D1523
Product name : Triethyl Phosphonoacetate
Purity: min. 97.0 %
Packaging: 25G
Price: ₹2000
Updated: 2022/05/26
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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.