Tsunoda reagent

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

Tsunoda reagent

CMBP, also known as Tsunoda reagent, is a stabilized trialkylphosphorane that serves as a versatile substitute for diethyl azodicarboxylate and triphenylphosphine in Mitsunobu reactions[1]. It exhibits comparable performance to triphenylphosphine and diethyl azodicarboxylate while combining their advantageous properties 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 pKa range for Mitsunobu reactions[2]. Additionally, CMBP offers a clean reaction profile, eliminating the need for phosphine nucleophile reagents and generating acetonitrile as an innocuous by-product, which often makes the process of purification simple. The CMBP-mediated reaction can be conducted at room temperature, yielding the desired product with exceptional yield and purity, but may require more time.

Synonyms: (Cyanomethylene)tributylphosphorane, CMBP, 2-(Tributylphosphoranylidene)acetonitrile, (Tributylphosphoranylidene)acetonitrile, 2-(tributyl-lambda5-phosphanylidene)acetonitrile

Selected publication

  1. (Tributylphosphoranylidene)Acetonitrile.

    Wyatt P. B. Encyclopedia of Reagents for Organic Synthesis 2008. DOI: 10.1002/047084289X.rn00790

  2. Novel Reactivity of Stabilized Methylenetributylphosphorane: A New Mitsunobu Reagent.

    Tsunoda T.; Ozaki F.; Itô S. Tetrahedron Lett 1994, 35 (28), 5081–5082. DOI: 10.1016/S0040-4039(00)73326-0