ID: 2490
Product Description: Ethyltriphenylphosphonium Iodide
Synonym: Ethyl(triphenyl)phosphanium;iodide
Email for a Quote Fill Out a Quote RequestCAS Number: 4736-60-1
EC Number: 225-245-2
MDL: MFCD00040352
Beilstein: 3659323
MF: C20H20IP
MW: 418.2
MOQ: 2kg
Minimum Purity: 98%
Pubchem: 78474
InChi Key: SLAFUPJSGFVWPP-UHFFFAOYSA-M
InChi: 1S/C20H20P.HI/c1-2-21(18-12-6-3-7-13-18,19-14-8-4-9-15-19)20-16-10-5-11-17-20;/h3-17H,2H2,1H3;1H/q+1;/p-1
SMILES: [I-].CC[P+](c1ccccc1)(c2ccccc2)c3ccccc3
Ethyl(triphenyl)phosphanium is a quaternary phosphonium salt with the CAS Number: 4736-60-1. It is an organic compound containing a phosphorus atom covalently bonded to four organic groups, giving the phosphorus atom a positive charge, which is balanced by a halide anion. This compound typically appears as a stable, white crystalline solid, which simplifies handling, storage, purification and accurate weighing for reactions.
This compound is commonly used as a precursor for the synthesis of phosphorus ylides generated by deprotonating the ethyltriphenylphosphonium salt with a strong base. The resulting phosphorus ylide is an indispensable reagent in organic synthesis. These salts generally exhibit good solubility in polar organic solvents, such as acetonitrile.
Ethyltriphenylphosphonium iodide is an indispensable and widely used reagent in organic chemistry for constructing complex molecular structures.
The Wittig reaction is a powerful synthetic method for forming carbon-carbon double bonds from carbonyl compounds. Ethyltriphenylphosphonium iodide serves as a precursor to the active reagent, enabling the selective formation of Z-alkenes from aldehydes and ketones.
The presence of positively charged phosphorus makes the hydrogen atoms on the adjacent carbon highly acidic. The strong base abstracts one of these α-protons, generating a neutral, zwitterionic species. This ethyltriphenylphosphonium ylide is characterized by a negatively charged carbon atom directly bonded to a positively charged phosphorus atom.
Once formed, the ethyltriphenylphosphonium ylide reacts with an aldehyde or ketone. The nucleophilic, negatively charged carbon of the ylide attacks the electrophilic carbon of the carbonyl group. The oxaphosphetane intermediate then rapidly collapses to yield a new alkene and triphenylphosphine oxide.
Ethyltriphenylphosphonium iodide can be employed in phase-transfer catalysis (PTC), like other quaternary phosphonium salts. PTC is a technique used in chemistry to facilitate the reaction between two or more reactants in different, immiscible phases, where they would normally not react or would react very slowly. The compound offers several advantages, including increased reaction rates, milder reaction conditions, improved selectivity and simpler workup.
Iofina offers high-purity, reliable reagents critical to achieving successful outcomes in sensitive synthesis reactions. As a primary producer of iodine and its derivatives, we have deep expertise in manufacturing high-quality halogenated compounds.
Our products meet stringent purity standards, ensuring lot-to-lot consistency for your processes. Fill out our online contact form to request a quote for ethyl triphenylphosphonium or to discuss your specific reagent needs.
