(Triphenylphosphoranylidene)acetaldehyde
[CAS# 2136-75-6]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: (Triphenylphosphoranylidene)acetaldehyde
• Synonyms: Formylmethylene triphenylphosphorane
• Molecular Formula: C₂₀H₁₇OP
• Molecular Weight: 304.32
• CAS Registry Number: 2136-75-6
• EC Number: 218-375-6
• SMILES: C1=CC=C(C=C1)P(=CC=O)(C2=CC=CC=C2)C3=CC=CC=C3

Properties

• Melting point: 185-188 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

(Triphenylphosphoranylidene)acetaldehyde is a notable compound in the field of organophosphorus chemistry, distinguished by its unique structure and versatile applications. This compound consists of a triphenylphosphoranylidene group attached to an acetaldehyde moiety, forming a molecule with significant chemical reactivity and utility in various chemical processes.

The discovery of (triphenylphosphoranylidene)acetaldehyde emerged from the exploration of phosphoranylidene derivatives and their applications in organic synthesis. The synthesis of this compound typically involves the reaction of triphenylphosphine with acetaldehyde under controlled conditions to form the phosphoranylidene derivative. The resulting product features a phosphorus atom double-bonded to a carbonyl group and bonded to three phenyl rings, which imparts unique electronic and steric properties to the molecule.

One of the key applications of (triphenylphosphoranylidene)acetaldehyde lies in its role as a reagent and intermediate in organic synthesis. The compound is used in various reactions, including the formation of phosphoranylidene derivatives, which are valuable in the synthesis of complex organic molecules. Its reactivity as a phosphoranylidene allows it to participate in condensation reactions, offering a pathway to synthesize a range of phosphorus-containing compounds.

In addition to its role in organic synthesis, (triphenylphosphoranylidene)acetaldehyde is utilized in the development of novel materials and chemical processes. The compound's ability to form stable complexes with other reagents and catalysts makes it useful in the design of new materials with specific properties. For example, its interaction with metal centers can lead to the formation of organometallic compounds with potential applications in catalysis, materials science, and electronics.

The study of (triphenylphosphoranylidene)acetaldehyde also contributes to the broader understanding of phosphorus chemistry and the design of phosphoranylidene derivatives. Researchers explore the properties of this compound to gain insights into the behavior of phosphoranylidene groups in various chemical contexts. This knowledge is valuable for developing new reagents and catalysts with enhanced performance and selectivity.

Overall, (triphenylphosphoranylidene)acetaldehyde represents an important compound in organophosphorus chemistry, with applications in organic synthesis, materials development, and chemical research. Its unique structure and reactivity make it a valuable tool for advancing both fundamental chemistry and practical applications.

References

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URL: SD-025-00553

2019. Recent advances in the applications of Wittig reaction in the total synthesis of natural products containing lactone, pyrone, and lactam as a scaffold. Monatshefte für Chemie - Chemical Monthly, 150(8).
DOI: 10.1007/s00706-019-02465-9

2012. A practical route to long-chain non-natural α,ω-diamino acids. Amino Acids, 43(5).
DOI: 10.1007/s00726-012-1349-0