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HomeProduct name listEthyl 2-(triphenylphosphoranylidene)propionate

Ethyl 2-(triphenylphosphoranylidene)propionate

Synonym(s):Ethyl 2-(triphenylphosphoranylidene)propionate

  • CAS NO.:5717-37-3
  • Empirical Formula: C23H23O2P
  • Molecular Weight: 362.4
  • MDL number: MFCD00009160
  • EINECS: 227-215-4
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-05-15 10:43:14
Ethyl 2-(triphenylphosphoranylidene)propionate Structural

What is Ethyl 2-(triphenylphosphoranylidene)propionate?

Chemical properties

yellow crystalline powder

The Uses of Ethyl 2-(triphenylphosphoranylidene)propionate

(1-Ethoxycarbonylethylidene)triphenylphosphorane is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals. It?s also a Horner-Wadsworth-Emmons reagent. It can be used for olefination. It can also be utilized for the synthesis of more complex compounds, such as (29S,37S)-isomer of malevamide E, a potent ion-channel inhibitor.

Synthesis

Ethyl 2-(triphenylphosphoranylidene)propionate was prepared this reagent from ethyl 2-bromopropanoate and triphenylphosphine.A 500-mL, one-necked, round-bottomed flask equipped with an egg-shaped magnetic stirring bar is charged with triphenylphosphine (52.46 g, 200.0 mmol), ethyl acetate (130 mL), and ethyl 2-bromopropanoate (26.03 mL, 200.0 mmol). A reflux condenser is attached to the flask and the solution is heated under reflux (oil bath temperature: 75-80 °C) under argon for 24 h. The resulting white precipitate is collected through suction filtration on a Büchner funnel and washed with ethyl acetate (100 mL). The salt is dissolved in dichloromethane (500 mL) and the solution is transferred to a 1-L separation funnel. Aqueous sodium hydroxide solution (2 M, 200 mL) is added and, after vigorously shaking, the organic and aqueous layers are separated. The aqueous phase is extracted with dichloromethane (100 mL). The combined organic phases are washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated at 30 °C under rotary evaporation (20-25 mmHg); drying under vacuum (0.1-0.2 mmHg) affords 54.51 g (75.2%) of ethyl 2-(triphenylphosphoranylidene)propionate as a light-yellow solid, mp 156-158 °C.

Properties of Ethyl 2-(triphenylphosphoranylidene)propionate

Melting point: 158-162 °C (lit.)
Boiling point: 497.2±28.0 °C(Predicted)
Density  1.14±0.1 g/cm3(Predicted)
storage temp.  2-8°C
solubility  Chloroform (Slightly), Methanol (Slightly)
form  Crystalline Powder
color  Yellow
Water Solubility  Soluble in water.
Sensitive  Air Sensitive
BRN  757112
CAS DataBase Reference 5717-37-3(CAS DataBase Reference)
NIST Chemistry Reference Propanoic acid, 2-(triphenylphosphoranylidene)-, ethyl ester(5717-37-3)

Safety information for Ethyl 2-(triphenylphosphoranylidene)propionate

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P260:Do not breathe dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P312:Call a POISON CENTER or doctor/physician if you feel unwell.

Computed Descriptors for Ethyl 2-(triphenylphosphoranylidene)propionate

InChIKey KZENFXVDPUMQOE-UHFFFAOYSA-N

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