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2-(tributyl-lambda5-phosphanylidene)acetonitrile
2-(tributyl-lambda5-phosphanylidene)acetonitrile

EN300-316330

Product class

Building Blocks

CAS number

157141-27-0

MW

241.35

Purity

95%

Stock Availability

UA, DE, US

Lead time

1-5 days delivery time

Product Details
Shipping Details

Reagent for Mitsunobu reaction

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
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
Name:
2-(tributyl-lambda5-phosphanylidene)acetonitrile
SMILES:
CCCCP(=CC#N)(CCCC)CCCC
CAS number:
157141-27-0
CLogP:
5.369
ACD number:
MFCD01321151
Dangerous good:
Yes
Class:
Lab Reagents
Formula:
C14H28NP
Subclass:
Nitriles
MW:
241.35
Product class:
Building Blocks