Propylphosphonic anhydride

Description

T3P is typically sold as a 50% solution in a solvent (ex. EtOAc or DMF).

Chemical properties

Clear light yellow solution

The Uses of Propylphosphonic anhydride

It is employed as an efficient promoter for the Lossen rearrangement to synthesis urea and carbamate derivatives.

The Uses of Propylphosphonic anhydride

To a solution of the SM (2.92 g, 9.89 mmol) in 2-methyl tetrahydrofuran (115 mL) was added DIEA (13.8 mL, 39.5 mmol) and cyclopropylamine (2.77 mL, 39.5 mmol). The resulting mixture was heated to 70 C and T3P (50% weight solution in DCE) (17.3 mL, 59.3 mmol) was added. The reaction mixture was heated at 70 C for 16 h and then diluted with EtOAc (200 mL). The mixture was then washed sequentially with sat aq Na2CO3 (100 mL), 10% aq citric acid (100 mL), and saturated aq Na2CO3 (100 mL). The combined org extracts were dried (MgSO4) and concentrated in vacuo to give an oil. The crude was purified by column chromatography (eluting with 50% EtOAc/heptane) to give a solid which was recrystallized with IPA to provide the product as a white solid. [2.46 g, 74%]

The Uses of Propylphosphonic anhydride

Propylphosphonic anhydride may be used in the following studies:

• As coupling agent for the synthesis of bispyridine-based ligands, which are used as bridging linkers in multinuclear platinum anticancer drugs.
• Microwave-assissted Fischer indolization of arylhydrazines.
• As acid activating agent for the direct synthesis of acid azides from carboxylic acids.
• One-pot synthesis of coumarins.
• Microwave-mediated synthesis of carbocyclic and heterocyclic fused quinolones.
• One-pot synthesis of 1,2,4-oxadiazoles, 1,3,4-oxadiazoles, and 1,3,4-thiadiazoles from carboxylic acids.
• Activation of the carboxyl group for hydroxyamidation and peptide coupling and in the one-pot conversion of carboxylic acids into hydroxamic acids.

General Description

Propylphosphonic anhydride (T3P) is a reactive n-propyl phosphonic acid cyclic anhydride. It is a mild and low toxic coupling agent used in peptide synthesis. T3P also acts as a promoter and water scavenger in the Friedl?nder annulation reaction. It participates in the conversion of carboxylic acids and amides into nitriles, formation of Weinreb amides, ester synthesis, dehydrations, oxidation of alcohols, isonitrile synthesis, synthesis of alkenes from alcohols and C-C coupling reactions. T3P delivers outstanding advantages over traditional reagents, such as broad functional group tolerance, low epimerization, and water-soluble by-products and hence gives high purity and yield of the product.

Flammability and Explosibility

Not classified