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(Ethoxycarbonylmethylene)triphenylphosphorane, 98+%, Thermo Scientific Chemicals
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Catalog number A12896.18
also known as A12896-18
Price (USD)/ Each
107.65
Online exclusive
119.00 Save 11.35 (10%)
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Quantity:
50 g
Price (USD)/ Each
107.65
Online exclusive
119.00 Save 11.35 (10%)
(Ethoxycarbonylmethylene)triphenylphosphorane, 98+%, Thermo Scientific Chemicals
Catalog numberA12896.18
Price (USD)/ Each
107.65
Online exclusive
119.00 Save 11.35 (10%)
-
Chemical Identifiers
CAS1099-45-2
IUPAC Nameethyl 2-(triphenyl-λ⁵-phosphanylidene)acetate
Molecular FormulaC22H21O2P
InChI KeyIIHPVYJPDKJYOU-UHFFFAOYSA-N
SMILESCCOC(=O)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
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Specifications
Specification Sheet
Specification SheetAssay (HPLC)≥98.0%
Appearance (Color)White to pale cream or pale yellow
FormCrystals or powder or crystalline powder
Identification (FTIR)Conforms
(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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
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.
Solubility
Soluble in organic solvents. Insoluble in water.
Notes
Air sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents.
(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.
Solubility
Soluble in organic solvents. Insoluble in water.
Notes
Air sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents.
RUO – Research Use Only
General 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 (Methoxycarbonyl methyl ene) triphenyl phosphorane, A14020, and Appendix 1.
- 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.