ChemicalBook > CAS DataBase List > Triethyl phosphonoacetate

Triethyl phosphonoacetate

Product Name
Triethyl phosphonoacetate
CAS No.
867-13-0
Chemical Name
Triethyl phosphonoacetate
Synonyms
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
Molecular Formula
C8H17O5P
Formula Weight
224.19
MOL File
867-13-0.mol
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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
Water Solubility 
Slightly miscible with water.
BRN 
1343714
InChIKey
GGUBFICZYGKNTD-UHFFFAOYSA-N
LogP
1.13 at 30℃
CAS DataBase Reference
867-13-0(CAS DataBase Reference)
EPA Substance Registry System
Acetic acid, (diethoxyphosphinyl)-, ethyl ester (867-13-0)
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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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H319Causes serious eye irritation

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

P391Collect spillage. Hazardous to the aquatic environment

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
79525
Product name
Triethyl phosphonoacetate
Purity
purum, ≥97.0% (GC)
Packaging
100ml
Price
$107
Updated
2024/03/01
Sigma-Aldrich
Product number
79525
Product name
Triethyl phosphonoacetate
Purity
purum, ≥97.0% (GC)
Packaging
500ml
Price
$397
Updated
2024/03/01
TCI Chemical
Product number
D1523
Product name
Triethyl Phosphonoacetate
Purity
>97.0%(GC)
Packaging
25g
Price
$29
Updated
2024/03/01
TCI Chemical
Product number
D1523
Product name
Triethyl Phosphonoacetate
Purity
>97.0%(GC)
Packaging
100g
Price
$63
Updated
2024/03/01
Alfa Aesar
Product number
A14120
Product name
Triethyl phosphonoacetate, 98+%
Packaging
100g
Price
$90.4
Updated
2024/03/01
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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.

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.

Triethyl phosphonoacetate Preparation Products And Raw materials

Raw materials

Preparation Products

Dihydrocaffeic acid 3-(2-FURYL)PROPANOIC ACID ETHYL 3-(2-FURYL)ACRYLATE 2-(AMINOMETHYL)CYCLOPROPANECARBOXYLIC ACID ETHYL 3-(2-FURYL)PROPIONATE (+/-)-4-AMINO-3-(5-CHLORO-2-THIENYL)-BUTANOIC ACID
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View Lastest Price from Triethyl phosphonoacetate manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Triethyl phosphonoacetate 867-13-0
Price
US $0.00/KG
Min. Order
1KG
Purity
98%min
Supply Ability
30tons/month
Release date
2023-01-09
Hebei Weibang Biotechnology Co., Ltd
Product
Triethyl phosphonoacetate 867-13-0
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500000kg
Release date
2024-10-31
Hebei Yanxi Chemical Co., Ltd.
Product
Triethyl phosphonoacetate 867-13-0
Price
US $30.00-7.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
20 tons
Release date
2023-10-07

867-13-0, Triethyl phosphonoacetate Related Search:

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  • AURORA KA-1452
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  • Ethyl(diethyoxyphosphoryl)acetate
  • Diethyl ethoxycarbonylmethylphosphonate, Triethyl carboxymethylphosphonate
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  • Diethoxyphosphinylacetic acid ethyl ester
  • Ethoxycarbonylmethylphosphonic acid diethyl ester
  • Acetic acid, phosphono-, triethyl ester
  • TRIETHYL PHOSPHONOACETATE ,97%
  • Triethyl phosphonoacetate,98.5%
  • 2-(Diethoxyphosphinyl)acetic Acid Ethyl Ester
  • CarbethoxyMethyldiethyl Phosphonate
  • NSC 13898
  • NSC 16128
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  • 867-13-0