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TCI

CAS 19816-88-7

1,3-Diphenylacetone p-Toluenesulfonylhydrazone TCI D2093

1,3-Diphenylacetone p-Toluenesulfonylhydrazone TCI D2093
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Description

TCI D2093 1,3-Diphenylacetone p-Toluenesulfonylhydrazone is a tosylhydrazone derivative formed from 1,3-diphenylacetone and p-toluenesulfonylhydrazide. In the organic chemistry laboratory, this compound is known as a practical carbene and diazo precursor: when treated with base and heat, the tosylhydrazone group decomposes, releasing sulfinate and nitrogen and thereby generating a reactive species without the need to handle hazardous free diazo compounds. This ability to generate reactive intermediates *in situ* is precisely what makes the reagent highly valuable to researchers developing carbon–carbon bond forming methods.

The characteristics that lead chemists to select it begin with its stability as a solid that is easy to weigh out and store, in contrast to liquid diazo precursors that demand special handling. The 1,3-diphenylacetone framework places two benzyl groups on either side of the carbonyl carbon, so the carbene or diazo anion that forms is stabilized while remaining able to continue on to an olefin or to combine with a coupling partner. This reagent is a classic substrate for the Bamford–Stevens and Shapiro reactions, and it is also widely used in the development of modern methodology.

In Indonesian laboratories, this material is typically found in university organic synthesis groups, research institute chemistry units, and methodology-focused laboratories exploring carbene and diazo chemistry. It is generally ordered in small research quantities alongside the bases and anhydrous solvents required for the decomposition step, and is kept as part of a specialty building block inventory where a stable solid precursor is preferred over reagents that require more demanding handling in routine bench work.

Laboratory Applications

  • Bamford–Stevens reaction studies: the tosylhydrazone group decomposes under base and heat to give a diazo intermediate that proceeds to the corresponding olefin, making this a classic substrate for teaching and probing this transformation.
  • Shapiro reaction work: chemists use this reagent as a standard tosylhydrazone substrate when investigating alkene formation pathways, since its well-defined dibenzyl framework gives predictable and easily interpreted reaction outcomes.
  • In situ carbene generation: laboratories choose this solid precursor to release the reactive carbene species directly in the flask, avoiding the storage and transfer of free diazo compounds that require far more demanding safety handling.
  • Carbon–carbon bond forming methodology development: researchers developing new coupling methods rely on this compound to supply a stabilized diazo or carbene partner that can combine with a coupling partner under investigation.
  • Modern synthetic methodology screening: because the reagent is a stable, easily weighed solid, it suits reaction screening campaigns where consistent dosing of a diazo precursor across many parallel experiments is required.

Specifications

  • Brand: TCI
  • CAS number: 19816-88-7
  • Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
  • Pack sizes: available in standard TCI research-scale packaging; please confirm the size options when ordering
  • Physical form: solid, which allows straightforward weighing and storage
  • Storage note: keep in the closed original container under the storage conditions stated on the manufacturer label

Handling and Storage

Store the container tightly closed in a cool, dry, well-ventilated chemical store, away from heat sources, open flames, and incompatible reagents, and follow the storage conditions printed on the manufacturer label. The original supplier container is the most suitable primary packaging; if transfer is necessary, use a clean, dry, chemically resistant and clearly labelled container. Handle the solid in a fume hood, wearing a laboratory coat, safety glasses, and appropriate gloves, and avoid generating dust during weighing. Because the tosylhydrazone group decomposes with base and heating to release nitrogen, keep the material away from strong bases and heat unless decomposition is intended as part of a controlled reaction. Consult the manufacturer safety data sheet before use and dispose of residues through the laboratory chemical waste stream.

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