431303

Propylphosphonic anhydride solution

≥50 wt. % in ethyl acetate

• Synonym(s): 1-Propanephosphonic anhydride solution, 2,4,6-Tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide solution, PPACA, T3P^®
• Empirical Formula (Hill Notation): C₉H₂₁O₆P₃
• CAS Number: 68957-94-8
• Molecular Weight: 318.18
• Beilstein: 5079255
• MDL number: MFCD00006583
• UNSPSC Code: 12352100
• PubChem Substance ID: 24867005
• NACRES: NA.22

Properties

• form: liquid
• Quality Level: 200
• concentration: ≥50 wt. % in ethyl acetate
• refractive index: n20/D 1.418
• bp: 65 °C
• density: 1.069 g/mL at 25 °C
• SMILES string: CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1
• InChI: 1S/C9H21O6P3/c1-4-7-16(10)13-17(11,8-5-2)15-18(12,14-16)9-6-3/h4-9H2,1-3H3
• InChI key: PAQZWJGSJMLPMG-UHFFFAOYSA-N

Description

General description

Propylphosphonic anhydride (T3P) is a reactive n-propyl phosphonic acid cyclic anhydride.[1] It is a mild and low toxic coupling agent used in peptide synthesis.[2] T3P also acts as a promoter and water scavenger in the Friedländer annulation reaction.[3] 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.[1] 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.[4][1]

Application

Propylphosphonic anhydride (T3P) can be used:

• As an acid-amine coupling reagent for the synthesis of 3-(trifluoromethyl)-1H-pyrazole-5-carboxamides which are potent activators of pyruvate kinase M2 (PKM2).[5]
• In the synthesis of substituted benzofurans as potent DNA gyraseB inhibitors of Mycobacterium tuberculosis.[6]
• As a catalyst in the synthesis of benzothiazoles, benzoxazoles, and benzimidazoles under microwave irradiation.[7]
• As a catalyst in the conversion of ketoximes to amides and aldoximes to nitriles via Beckmann rearrangement.[8]
• As a reagent in the one-pot conversion of aromatic, heteroaromatic, and aliphatic aldehydes to nitriles.[9]

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.[10]
• Microwave-assissted Fischer indolization of arylhydrazines.[11]
• As acid activating agent for the direct synthesis of acid azides from carboxylic acids.[12]
• One-pot synthesis of coumarins.[2]
• Microwave-mediated synthesis of carbocyclic and heterocyclic fused quinolones.[3]
• One-pot synthesis of 1,2,4-oxadiazoles, 1,3,4-oxadiazoles, and 1,3,4-thiadiazoles from carboxylic acids.[1]
• Activation of the carboxyl group for hydroxyamidation and peptide coupling and in the one-pot conversion of carboxylic acids into hydroxamic acids.[13][14]

Legal Information

T3P is a registered trademark of Archimica GmbH

Safety Information

• Pictograms: GHS02,GHS05,GHS07
• Signal Word: Danger
• Hazard Statements: H225,H290,H314,H317,H336
• Precautionary Statements: P210 - P233 - P234 - P280 - P303 + P361 + P353 - P305 + P351 + P338
• Hazard Classifications: Eye Dam. 1 - Flam. Liq. 2 - Met. Corr. 1 - Skin Corr. 1B - Skin Sens. 1 - STOT SE 3
• Target Organs: Central nervous system
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 1
• Flash Point(F): 24.8 °F - closed cup
• Flash Point(C): -4 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves