• 2226728-58-9 2-(1,3-Dioxoisoindolin-2-yl)-1,1,3,3-tetramethylisouronium Hexafluorophosphate - AMI Scientific
  • 2-(1,3-Dioxoisoindolin-2-yl)-1,1,3,3-tetramethylisouronium Hexafluorophosphate - brosur TCI: Condensing Agent Enabling Redox Active Ester (RAEs) Formation
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TCI

CAS 2226728-58-9

2-(1,3-Dioxoisoindolin-2-yl)-1,1,3,3-tetramethylisouronium Hexafluorophosphate TCI P3322

2-(1,3-Dioxoisoindolin-2-yl)-1,1,3,3-tetramethylisouronium Hexafluorophosphate TCI P3322

Chemical Identity

Other names
PITU
CAS No.
2226728-58-9
Purity
>98.0%(HPLC)(qN
Rp 1.483.650,00
Rp 1.053.150,00 Rp 1.483.650,00
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TCI P3322, 2-(1,3-Dioxoisoindolin-2-yl)-1,1,3,3-tetramethylisouronium Hexafluorophosphate, is a uronium/isouronium salt coupling reagent that carries a phthalimide group. Its structure resembles popular coupling reagents such as HBTU, but its activating group comes from N-hydroxyphthalimide. In organic synthesis laboratories it is used to activate carboxylic acids, mainly to form N-(acyloxy)phthalimide esters. These esters are known as redox-active esters and are widely used in modern radical chemistry.

Its main advantage is that it converts a carboxylic acid directly into an active ester in a single step. This approach avoids using a carbodiimide and N-hydroxyphthalimide as separate components. The procedure is therefore shorter, and purification can be simpler because no urea by-products from carbodiimides need to be removed. The redox-active esters it produces are key precursors for decarboxylative reactions, such as nickel-catalysed cross-coupling and photoredox transformations. The hexafluorophosphate anion makes the reagent a solid salt that is easy to weigh accurately.

In Indonesia, this reagent suits organic chemistry and medicinal chemistry laboratories that are starting to use photocatalysis and other radical-based synthetic methods. University research groups, pharmaceutical development laboratories and synthetic chemistry teams can use it to make redox-active esters from many different carboxylic acids. Because it simplifies the activation step, it fits well in methodology development, building-block preparation and the exploratory synthesis of new compounds for research projects.

Advantages (TCI brochure)

  • Enables easy preparation of redox active esters (RAEs)
  • Suitable for in situ decarboxylative cross coupling via electrochemical reactions
  • Available in large quantities to support bulk supply requirements

TCI brochures (PDF)

Related TCI products

  • Carboxylic acid activation: the reagent turns carboxylic acids directly into N-(acyloxy)phthalimide active esters in one step, without a separate carbodiimide.
  • Redox-active ester preparation: it gives straightforward access to the N-(acyloxy)phthalimide esters used as radical precursors in modern decarboxylative radical chemistry.
  • Nickel-catalysed decarboxylative cross-coupling: the esters it produces are important starting materials for nickel-catalysed reactions that build new carbon–carbon bonds from carboxylic acids.
  • Photoredox catalysis research: laboratories studying visible-light photoredox reactions can use the redox-active esters it forms as convenient sources of carbon-centred radicals.
  • Medicinal chemistry building-block synthesis: its single-step activation and simpler purification help chemists turn diverse carboxylic acids into new structural fragments more efficiently.

From the TCI brochure

  • Preparation of RAE from a carboxylic acid with DIPEA as base in CH2Cl2 at r.t.
  • Decarboxylative sp2–sp3 cross-coupling with NiCl2dme (cat.), dtbbpy (cat.), NaI in DMA at r.t. under electrochemical conditions, using sodium carboxylates as starting materials

Brand TCI (product code P3322)
CAS number 2226728-58-9
Molecular formula —
Purity —
Category Chemistry > Synthetic Reagents > Coupling [Synthetic Reagents]
Pack sizes as listed on the product page
Physical form solid (hexafluorophosphate salt)
Storage follow the conditions on the TCI label and Safety Data Sheet

Store this reagent in its original, tightly closed container, as stated on the manufacturer's label and Safety Data Sheet. Keep it in a cool, dry, well-ventilated area away from moisture, heat and incompatible materials. Like other coupling reagents, it should be protected from humidity to keep it reactive, so reseal the container promptly after use. Weigh and handle it in a fume hood or a well-ventilated area. Wear suitable personal protective equipment, including a lab coat, safety glasses and chemical-resistant gloves. Avoid creating dust, breathing it in, or letting it touch skin and eyes. Dispose of waste according to institutional and local chemical waste regulations.

References cited in the TCI brochure

  1. Jiang Wang. Ketones from Nickel‐Catalyzed Decarboxylative, Non‐Symmetric Cross‐Electrophile Coupling of Carboxylic Acid Esters Angewandte Chemie International Edition, 2019. doi:10.1002/anie.201906000
  2. Takaoki Koyanagi. One-Pot Electrochemical Nickel-Catalyzed Decarboxylative Sp2–Sp3 Cross-Coupling Organic Letters, 2019. doi:10.1021/acs.orglett.8b04090

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