TCI D2580 Dodecylbenzenesulfonyl Azide (soft type) (mixture) is a synthetic reagent belonging to the group of reagents used for carbon–heteroatom (non-halogen) bond formation. Its primary laboratory function is as a diazo transfer reagent, meaning it delivers a diazo group to compounds bearing an active hydrogen — such as 1,3-dicarbonyl compounds, beta-ketoesters, and malonates — to form alpha-diazocarbonyl compounds. The diazo compounds produced in this reaction are highly useful intermediates, because they can be decomposed into carbenes or metal carbenoids for cyclopropanation, C–H insertion, and rearrangement reactions.
The characteristic that makes this reagent a preferred choice is its handling profile. Short-chain aryl sulfonyl azides such as tosyl azide are known to be sensitive to impact and heat, whereas this "soft type" product is supplied as a mixture formulation with a long dodecyl chain that appreciably reduces that sensitivity and makes the reagent far more convenient to use in a research laboratory setting. The long alkyl chain on the benzene ring also improves solubility in non-polar organic solvents and simplifies separation of the sulfonamide by-product during work-up, which together support smoother, more reproducible synthetic procedures.
In Indonesian laboratories, this reagent is typically used in organic synthesis and methodology research groups at universities, research institutes, and industrial R&D units that prepare alpha-diazocarbonyl intermediates in-house. It suits work programmes in which diazo transfer is performed on a bench scale for further carbene-based transformations, and where a less impact- and heat-sensitive alternative to short-chain sulfonyl azides is preferred so that routine synthetic work can proceed with more comfortable handling requirements.
- Diazo transfer to 1,3-dicarbonyl compounds — the reagent delivers the diazo group to active-hydrogen substrates directly, giving access to alpha-diazocarbonyl products without resorting to more impact-sensitive short-chain sulfonyl azides.
- Preparation of alpha-diazo beta-ketoesters — beta-ketoesters are classic active-methylene substrates for this reagent, and the resulting diazo esters serve as stable-handling intermediates for downstream carbene chemistry.
- Diazo functionalisation of malonate derivatives — malonates possess the activated hydrogens required for diazo transfer, and the reagent's good solubility in non-polar solvents helps keep such reaction mixtures homogeneous.
- Precursor synthesis for cyclopropanation studies — diazocarbonyl compounds made with this reagent decompose to carbenes or metal carbenoids, which are the working species used to build cyclopropane rings.
- Substrate preparation for C–H insertion and rearrangement work — the same metal carbenoid intermediates generated from these diazo compounds are used in C–H insertion and rearrangement reactions in methodology research.
| Brand | TCI (Tokyo Chemical Industry) |
|---|---|
| CAS number | 79791-38-1 |
| Molecular formula | — |
| Purity | — |
| Category | Chemistry > Synthetic Reagents > C-X(Non-Halogen) Bond Formation [Synthetic Reagents] |
| Pack sizes | — |
| Physical form | supplied as a "soft type" mixture formulation containing the long-chain dodecylbenzenesulfonyl azide |
| Storage | store according to the manufacturer's stated conditions on the product label and Safety Data Sheet |
- Product code: D2580
Store the reagent in its original tightly closed container, kept in a cool, dry, well-ventilated area away from heat sources, direct sunlight, ignition sources, and incompatible materials, and follow the storage conditions stated by the manufacturer on the label and Safety Data Sheet. Although the soft type mixture formulation is markedly less sensitive to impact and heat than short-chain aryl sulfonyl azides, sulfonyl azides as a class still warrant careful handling: avoid friction, shock, and unnecessary heating or concentration to dryness. Handle in a fume hood using appropriate gloves, safety glasses, and a laboratory coat, keep containers closed when not in use, and review the Safety Data Sheet before work.
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