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Description
TCI D4074 Diethyl (1,3-Dithian-2-yl)phosphonate is a synthetic reagent that combines a 1,3-dithiane ring with a diethyl phosphonate group at the 2-position. This combination makes it a characteristic reagent for carbon–carbon bond formation through the Horner–Wadsworth–Emmons approach. In the laboratory, the compound is used to convert aldehydes and ketones into ketene dithioacetals, that is, alkene products carrying two sulfur atoms on a single carbon. That structure can subsequently be hydrolysed to give a carbonyl group that has been shifted by one carbon atom, so the reagent functions as an effective homologation strategy for chain extension work.
The characteristic that leads chemists to select this reagent is the umpolung behaviour it brings to a synthesis. The carbon at the 2-position of the dithiane ring, which is naturally electrophilic in its carbonyl form, here behaves as a nucleophile once it has been deprotonated by a strong base. The phosphonate anion that forms is sufficiently stable and reacts with carbonyl compounds to give alkenes, releasing a phosphate salt that is easily separated during the final work-up stage. The dithiane group also serves as a carbonyl protecting group that withstands many reaction conditions and can afterwards be reopened.
In Indonesian laboratories, a reagent of this type is normally handled within university research groups, institutional synthetic chemistry facilities, and industrial research units engaged in multi-step organic synthesis. It is typically used in small-scale reactions on the bench under anhydrous conditions, where a defined carbon–carbon bond-forming step or a carbonyl homologation sequence is required. Because it is supplied as a catalogue reagent under the TCI brand, it fits routine procurement for research programmes that rely on well-characterised building blocks.
Laboratory Applications
Horner–Wadsworth–Emmons olefination: the diethyl phosphonate group forms a stabilised anion on deprotonation that reacts cleanly with carbonyl compounds to deliver the alkene product.
Ketene dithioacetal preparation: reaction with aldehydes and ketones installs an alkene bearing two sulfur atoms on one carbon, giving direct access to this structural motif.
One-carbon homologation of carbonyl compounds: the ketene dithioacetal formed can be hydrolysed to a carbonyl group shifted by one carbon along the chain.
Umpolung-based carbon–carbon bond construction: the dithiane 2-position acts as a nucleophile rather than an electrophile, allowing disconnections that normal carbonyl reactivity does not permit.
Carbonyl protection during multi-step synthesis: the dithiane ring tolerates many reaction conditions and can be reopened later, so it protects the masked carbonyl through intermediate steps.
Specifications
Brand: TCI
CAS number: 62999-73-9
Chemical name: Diethyl (1,3-Dithian-2-yl)phosphonate
Pack sizes: available in standard TCI catalogue pack sizes; please confirm the required size when ordering
Storage note: keep tightly closed in a cool, dry, well-ventilated place away from moisture
Handling and Storage
Store the reagent in its original tightly closed container in a cool, dry and well-ventilated area, away from moisture and from direct sunlight or other heat sources. Because the compound is used in reactions that require strong bases and anhydrous conditions, keep the container sealed between uses and avoid unnecessary exposure to atmospheric humidity. Handle it inside a fume hood, since organosulfur reagents commonly carry a persistent odour, and wear a laboratory coat, chemical-resistant gloves and safety goggles. Transfer with clean, dry glassware or syringes, keep it separated from strong oxidising agents, and follow the manufacturer's safety data sheet together with your institutional chemical waste procedures.
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