(Carbethoxymethylene)triphenyl Phosphorane, identified by CAS Number 1099-45-2, is a widely used Wittig reagent in organic synthesis. This phosphorus ylide plays a crucial role in carbon–carbon double bond formation, making it an essential intermediate in pharmaceutical, agrochemical, and fine chemical research.
Due to its reliability, selectivity, and predictable reactivity, (Carbethoxymethylene)triphenyl phosphorane is frequently employed in academic research and industrial synthesis for constructing α,β-unsaturated esters and related compounds.
Chemical Identification
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Product Name: (Carbethoxymethylene)triphenyl Phosphorane
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CAS Number: 1099-45-2
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Molecular Formula: C₂₂H₂₁O₂P
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Molecular Weight: ~348.38 g/mol
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Chemical Class: Phosphorus Ylide / Wittig Reagent
Physical & Chemical Properties
| Property | Description |
|---|---|
| Appearance | White to off-white crystalline solid |
| Purity | Typically ≥95% |
| Solubility | Soluble in common organic solvents |
| Stability | Stable under dry, inert conditions |
| Reactivity | Strong nucleophilic carbon center |
The compound should be handled under controlled laboratory conditions to preserve stability and reactivity.
Role in the Wittig Reaction
(Carbethoxymethylene)triphenyl phosphorane is best known for its role in the Wittig olefination reaction, where it reacts with aldehydes or ketones to form alkenes with ester functionality.
Key Advantages
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High chemoselectivity
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Predictable alkene formation
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Excellent control over carbon skeleton construction
These features make it indispensable for synthesizing complex organic molecules.
Key Uses of (Carbethoxymethylene)triphenyl Phosphorane
1. Organic Synthesis
Widely used to introduce α,β-unsaturated ester groups, which are valuable intermediates in:
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Natural product synthesis
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Drug discovery programs
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Functional material development
Conclusion
(Carbethoxymethylene)triphenyl Phosphorane (CAS 1099-45-2) is a cornerstone reagent in modern organic chemistry. Its role in Wittig reactions, combined with its importance in pharmaceutical, agrochemical, and natural product synthesis, makes it an indispensable tool for researchers worldwide.
When sourced at high purity and handled correctly, this phosphorus ylide delivers reliable performance in advanced chemical synthesis and research applications.
