Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

1099-45-2 - (Ethoxycarbonylmethylene)triphenylphosphorane, 98+% - (Carboethoxymethylene)triphenylphosphorane - Ethyl (triphenylphosphoranylidene)acetate - A12896 - Alfa Aesar

A12896 (Ethoxycarbonylmethylene)triphenylphosphorane, 98+%

CAS Number
1099-45-2
Synonyms
(Carboethoxymethylene)triphenylphosphorane
Ethyl (triphenylphosphoranylidene)acetate

Size Price ($) Quantity Availability
10g 24.82
50g 98.16
250g 400.67
Add to Cart Add to Quote Request View Item

(Ethoxycarbonylmethylene)triphenylphosphorane, 98+%

MDL
MFCD00009183
EINECS
214-151-7

Chemical Properties

Formula
CH3CH2O2CCH=P(C6H5)3
Formula Weight
348.38
Melting point
126-130°
Sensitivity
Air Sensitive
Solubility
Soluble in organic solvents. Insoluble in water.

Applications

(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.

Notes

Air sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents.

Literature References

Stable crystalline ylide which reacts with aldehydes giving substituted ethyl acrylates. This reaction has been used in an indole synthesis from o-nitrobenzaldehydes: Synthesis, 862 (1984); 401 (1987):

Coumarins have been synthesized from o-hydroxy acetophenones: Monatsh. Chem., 115, 765 (1984); o-hydroxy aldehydes give the 4-unsubstituted analogues: Chem. Pharm. Bull., 39, 3100 (1991); 42, 2032 (1994); Indian J. Chem. B, 32, 1159 (1993):

More highly-substituted ylides can be prepared by alkylation (e.g. with benzyl bromide) and abstraction of a proton by NaOH. See, e.g.: Synth. Commun., 19, 1899 (1989).

Reaction with acid chlorides leads to esters of allenic acids. See, e.g.: Org. Synth. Coll., 7, 232 (1990).

See also (Methoxycarbonyl­methyl­ene)­triphenyl­phosphorane, A14020, and Appendix 1.

/n

Bujaranipalli, S.; Das, S. Synthesis of (3R,5S)-5-hydroxy-de-O-methyllasiodiplodin: a facile and stereoselective approach. Tetrahedron Lett. 2015, 56 (24), 3747-3749.

Nagaraju, K.; Mainkar, P. S.; Chandrasekhar, S. Convergent synthesis of fully functionalized decalin skeleton of (+)-fusarisetin A. Tetrahedron Lett. 2015, 56 (2), 404-405.

Other References

Beilstein
754639
Harmonized Tariff Code
2931.90
TSCA
Yes

Recommended

Recently Viewed

Chemicals

Life Science

Metals & Materials

Catalysts

Analytical & Labware