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Ethyl (triphenylphosphoranylidene)acetate

Ethyl (triphenylphosphoranylidene)acetate Basic information
Description
Product Name:Ethyl (triphenylphosphoranylidene)acetate
Synonyms:(triphenylphosphoranylidene)-aceticaciethylester;(ETHOXYCARBONYLMETHYLENE)TRIPHENYLPHOSPHORANE;ETHYL (TRIPHENYLPHOSPHORANYLIDEN)ACETATE;ETHYL (TRIPHENYLPHOSPHORANYLIDENE)ACETATE;ETHYL (TRIPHENYLPHOSPHORYLIDENE)ACETATE;EMY;(CARBOETHOXYMETHYLENE)TRIPHENYLPHOSPHORANE;(CARBETHOXYMETHYLENE)TRIPHENYLPHOSPHORANE
CAS:1099-45-2
MF:C22H21O2P
MW:348.37
EINECS:214-151-7
Product Categories:Synthetic Organic Chemistry;Wittig & Horner-Emmons Reaction;Wittig Reaction;Intermediates & Fine Chemicals;Pharmaceuticals;bc0001
Mol File:1099-45-2.mol
Ethyl (triphenylphosphoranylidene)acetate Structure
Ethyl (triphenylphosphoranylidene)acetate Chemical Properties
Melting point 128-130 °C (lit.)
Boiling point 490.4±28.0 °C(Predicted)
density 1.086 g/cm3
storage temp. 2-8°C
solubility Chloroform, THF
form Powder
color White to light yellow
Water Solubility Insoluble
Sensitive Air Sensitive
BRN 754639
InChIKeyIIHPVYJPDKJYOU-UHFFFAOYSA-N
CAS DataBase Reference1099-45-2(CAS DataBase Reference)
EPA Substance Registry SystemAcetic acid, (triphenylphosphoranylidene)-, ethyl ester (1099-45-2)
Safety Information
Hazard Codes T,Xi,Xn
Risk Statements 36/37/38-25-20/21/22
Safety Statements 22-24/25-45-37/39-26-36
RIDADR UN2811
WGK Germany 3
Hazard Note Irritant
TSCA Yes
HS Code 29310095
MSDS Information
ProviderLanguage
(Carbethoxymethylene)triphenylphosphorane English
SigmaAldrich English
ACROS English
ALFA English
Ethyl (triphenylphosphoranylidene)acetate Usage And Synthesis
DescriptionEthyl (triphenylphosphoranylidene)acetate is a common Wittig reagent in organic synthesis as well as a cholinesterase inhibitor that inhibits both AChE and BChE. It is used in the preparation of indole from o-nitrobenzaldehydes, coumarins from o-hydroxy acetophenone.
Chemical PropertiesOff-White Solid
UsesA common Wittig reagent. A cholinesterase inhibitor.
Uses(Ethoxycarbonylmethylene)triphenylphosphoran is used as a Wittig reagent in organic synthesis. It is used in the preparation of indole from o-nitrobenzaldehydes, coumarins from o-hydroxy acetophenone. It acts as an inhibitor and inhibits the activity of cholinesterase.
Purification MethodsCrystallise it by dissolving it in AcOH and adding pet ether (b 40-50o) to give colourless plates. UV (A 1% ): 222nm (865) and 268nm (116) [Isler et max 1mm al. Helv Chim Acta 40 1242 1957]. [Beilstein 16 IV 977.]
Ethyl (triphenylphosphoranylidene)acetate Preparation Products And Raw materials
Preparation Products2-Oxo-(2H)-furo(2,3-h)-1-benzopyran-->8-HYDROXY-7-METHOXYCOUMARIN-->Scopoletin-->[1-(Ethoxycarbonyl)ethyl]triphenylphosphonium bromide-->Ethyl 4-methoxycinnamate-->(Carbethoxymethyl)triphenylphosphonium bromide-->2,4-HEPTADIEN-1-OL-->7,8-Dihydroxycoumarin-->(1-BENZYLPIPERIDIN-4-YLIDENE)ACETIC ACID ETHYL ESTER
Tocopheryl acetate DIMETHYL-P-NITROPHENYLPHOSPHATE Sodium acetate Ethyltriphenylphosphonium iodide 2,3-Butanedione Butyl acetate ACETATE Amyl acetate Ethyl acetate Triacetin Vinyl acetate Ethylene dimethacrylate Benzyl acetate Potassium Acetate Triphenylphosphine N,N-Dimethylacetamide Methyl acetate Ethyltriphenylphosphonium acetate
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