Tsunoda reagent

CAS 157141-27-0, Cat. No EN300-316330
Reagent for the Mitsunobu reaction

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(Cyanomethylene)tributylphosphorane (CMBP or Tsunoda reagent) is a stabilized trialkylphosphorane that serves as a versatile substitute for diethyl azodicarboxylate (DEAD) and triphenylphosphine (PPh₃) in the Mitsunobu reaction¹. It exhibits comparable performance to PPh3 and DEAD combining advantages within a single molecule. What sets CMBP apart is its enhanced reactivity and compatibility with high temperatures, enabling the utilization of weakly acidic pronucleophiles beyond the typical pK_a range for the Mitsunobu reaction². Additionally, CMBP offers a clean reaction profile, eliminating the need for phosphine nucleophile reagents and generating acetonitrile as an innocuous by-product, leading to a simple purification process. The CMBP-mediated reaction is carried out at ambient temperature, leading to the product with excellent yield and purity, but may require more time.

Synonyms: (cyanomethylene)tributylphosphorane; CMBP; 2-(tributylphosphoranylidene)acetonitrile; (tributylphosphoranylidene)acetonitrile; 2-(tributyl-lambda5-phosphanylidene)acetonitrile