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431303

Sigma-Aldrich

Propylphosphonic anhydride solution

≥50 wt. % in ethyl acetate

Synonym(s):
PPACA, 2,4,6-Tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide solution, T3P, 1-Propanephosphonic anhydride solution
Empirical Formula (Hill Notation):
C9H21O6P3
CAS Number:
Molecular Weight:
318.18
Beilstein:
5079255
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

liquid

Quality Level

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

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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 Friedländer 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.

Application

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.
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).
  • In the synthesis of substituted benzofurans as potent DNA gyraseB inhibitors of Mycobacterium tuberculosis.
  • As a catalyst in the synthesis of benzothiazoles, benzoxazoles, and benzimidazoles under microwave irradiation.
  • As a catalyst in the conversion of ketoximes to amides and aldoximes to nitriles via Beckmann rearrangement.
  • As a reagent in the one-pot conversion of aromatic, heteroaromatic, and aliphatic aldehydes to nitriles.

Packaging

10, 50, 100, 500 mL in glass bottle
2.5 L in glass bottle

Legal Information

T3P is a registered trademark of Archimica GmbH

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Dam. 1 - Flam. Liq. 2 - Met. Corr. 1 - Skin Corr. 1B - 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

Certificate of Analysis

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Certificate of Origin

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