TCI
Dimethyl 2-(1,3-Dithiole)phosphonate TCI D3981
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Description
TCI D3981 Dimethyl 2-(1,3-Dithiole)phosphonate is a heterocyclic building block that combines a 1,3-dithiole ring with a dimethyl phosphonate group in a single molecule. The reagent is best known as a key precursor in synthetic routes toward tetrathiafulvalene (TTF) and its derivatives, a family of electron-donor molecules that form the backbone of organic conductor research. In the laboratory, the compound serves as a phosphonate-stabilised carbanion component that can be coupled with carbonyl compounds to form carbon-carbon double bonds in a controlled manner.
The property that makes this reagent valuable is its ability to undergo the Horner-Wadsworth-Emmons reaction. The phosphonate group stabilises the carbanion generated after deprotonation with a strong base, and the by-product is a water-soluble phosphate salt that is easily separated during the final work-up stage. This advantage makes the olefination reaction cleaner than some of the alternatives. At the same time, the sulfur-rich 1,3-dithiole ring contributes strong electron-donor character to the final product, while also supplying sulfur atoms that participate in intermolecular interactions in solid-state materials. The combination of these two features makes the reagent a targeted choice rather than a general-purpose one.
In Indonesian laboratories, this building block is typically used by university and institutional research groups working on organic synthesis and functional materials. It appears in projects where a specific dithiole-containing fragment must be introduced into a larger molecular framework, and where researchers require a defined, ready-to-use reagent instead of preparing the heterocyclic phosphonate in-house. Its role is usually that of a specialist intermediate within a multi-step synthetic sequence rather than a routine bench chemical.
Laboratory Applications
- Tetrathiafulvalene (TTF) synthesis — the reagent is a recognised precursor in TTF routes, delivering the 1,3-dithiole unit that defines the electron-donor core of this molecular family.
- Horner-Wadsworth-Emmons olefination — the phosphonate group stabilises the carbanion after deprotonation with strong base, giving controlled carbon-carbon double bond formation with carbonyl partners.
- Organic conductor materials research — TTF derivatives prepared from this building block underpin studies of electron-donor systems investigated as organic conducting materials.
- Heterocyclic building block coupling — laboratories use it to introduce an intact, sulfur-rich 1,3-dithiole ring into larger frameworks during multi-step synthetic sequences.
- Solid-state and supramolecular studies — the sulfur atoms of the dithiole ring contribute to intermolecular interactions that influence how the resulting materials pack and behave.
Specifications
- Brand: TCI
- CAS number: 133113-76-5
- Product code: D3981
- Chemical name: Dimethyl 2-(1,3-Dithiole)phosphonate
- Category: Chemistry > Building Blocks > Heterocyclic Building Blocks
- Pack sizes and physical form: as listed on the current TCI catalogue entry for this product code; storage per the manufacturer's label and safety data sheet
Handling and Storage
Store the container tightly closed in a cool, dry, well-ventilated area, away from heat sources, direct sunlight, and incompatible materials, following the storage conditions stated on the manufacturer's label and safety data sheet. Keep the reagent in its original supplier container or in a comparable tightly sealed glass container with a chemically resistant closure, and reseal promptly after each use. Handle in a fume hood using standard personal protective equipment: safety goggles, chemically resistant gloves, and a laboratory coat. As with other organophosphorus reagents and sulfur-containing building blocks, avoid inhalation of vapour, avoid contact with skin and eyes, and label all working aliquots clearly. Consult the safety data sheet before use, and dispose of residues and contaminated materials through your institution's chemical waste procedures.
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