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1-Propylphosphonic acid cyclic anhydride is used in the synthesis of N-acyloxythiazole-2(3H)-thiones. It is also used to promote the synthesis of hydroxamic acids from carboxylic acids. Further, it is employed as an efficient promoter for the Lossen rearrangement to synthesis urea and carbamate derivatives.
T3P is a registered trademark of Clariant Group.
Condensation agent in formation of amide and ester linkages. In peptide synthesis, gives high yields, low racemization, and minimization of side reactions without the need for additives, as well as easily removable (water soluble) by-products: Angew. Chem. Int. Ed., 19, 133 (1980). Also reported for formation of a Weinreb amide in high yield from the acid and N,O-dimethylhydroxylamine: Angew. Chem. Int. Ed., 36, 1191 (1997). Activating agent for epoxidation of alkenes, giving cis-stereoselectivity in reactions with allylic alcohols: Tetrahedron Lett., 35, 8125 (1994). For a brief reviews of the reagent, see: Synlett, 1369 (2000); 1328 (2007). For peptide reagents, see Appendix 6.
Nand, B.; Khanna, G.; Chaudhary, A.; Lumb, A.; M Khurana, J. 1, 8-Diazabicyclo [5.4. 0] undec-7-ene (DBU): A Versatile Reagent in Organic Synthesis. Curr. Org. Chem. 2015, 19 (9), 790-812
Nagendra, G.; Madhu, C.; Vishwanatha, T. M.; Sureshbabu, V. V. An expedient route for the reduction of carboxylic acids to alcohols employing 1-propanephosphonic acid cyclic anhydride as acid activator. Tetrahedron Lett. 2012, 53 (38), 5059-5063.
Hazard Statements: H225-H314-H318-H336
Highly flammable liquid and vapour. Causes severe skin burns and eye damage. Causes serious eye damage. May cause drowsiness or dizziness.
Precautionary Statements: P210-P260u-P303+P361+P353-P305+P351+P338-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.