CYTOP® 330 – Trialkylphosphine for Pharmaceuticals and Catalysis

CYTOP® 330 – Trialkylphosphine for Pharmaceuticals and Catalysis

Cost-Effective Phosphine Enabling a Wide Range of Synthesis

CYTOP® 330 (tri-n-propylphosphine) (Strem Catalog # 15-7610) is a trialkylphosphine similar in size and basicity to triethylphosphine, at a significantly lower price point and ready for commercial scales. Although it is less known than similar trialkylphosphines – triethyl and tributyl phosphine – its reactivity is just as diverse. CYTOP® 330 (Strem Catalog # 15-7610) represents one among many trialkylphosphines available from Solvay (commercial scale) and Strem (commercial sampling and research quantities).

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CYTOP® 330
(Strem Catalog # 15-7610)

One application of CYTOP® 330 (Strem Catalog # 15-7610), as an alkyl phosphine, is its use as a Wittig reagent in pharmaceutical reactions (1). The novel phosphonium salts employed were accessed via a highly efficient, regioselective addition of hydrogen bromide to styrenes. Application of the α-methylstilbenes in the synthesis of a collection of stilbenoid-triazoles inhibits CYP45019A1 (aromatase) and, as such, leads to promising routes to medical candidates.

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CYTOP® 330 (Strem Catalog # 15-7610) can also act as a ligand for catalysis (2,3) for carboallylation of alkenes and nickel-based catalysis for olefin oligomeriations (including dimerization’s, trimerizations and tetramerizations). Additionally, it has been employed as a ligand for photocurable coatings (4). Studies have explored CYTOP® 330 (Strem Catalog # 15-7610) as a support ligand in the synthesis of quantum dots and nanoparticles (5) and in production of polyisocyanurate plastics (6).

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CYTOP® 330 (Strem Catalog # 15-7610) is a clear, colorless, pyrophoric liquid.   A tertiary phosphine, tri-n-propylphosphine must be handled under an inert atmosphere.  It can readily be functionalized into phosphonium salts or oxidized with hydrogen peroxide or sulfur to synthesize the relevant phosphine oxide and chalcogenides. To learn more about other ligands for catalysis, please refer to the Solvay offering at Strem or on the Solvay website.

 

References:

  1. Bioorganic & Medicinal Chemistry Letters, 2019, 29, 1395-1398.
  2. Organic Letters, 2019, 21, 4407-4410.
  3. World Patent WO 2017102689, June 22, 2017.
  4. World patent WO 2017208837, Dec. 7, 2017.
  5. Chinese Patent CN 107236536, Oct. 10, 2017.
  6. Chinese Patent CN 107216869, September 29, 2017.
  7. World Patent WO 2018039795, March 8, 2019.

 

Featured Product:

15-7610 Tripropylphosphine, min. 98%, CYTOP® 330

CAS Number: 2234-97-1

 

Related Products:

CYTOP Products

Phosphorus Ligands and Compounds Booklet

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