CYANOMETHYLENETRIBUTYLPHOSPHORANE

CYANOMETHYLENETRIBUTYLPHOSPHORANE Basic information
Product Name:CYANOMETHYLENETRIBUTYLPHOSPHORANE
Synonyms:Acetonitrile,2-(tributylphosphoranylidene)-;(Tributylphosphoranylidene)acetonitrile;(Tributylphosphoranylidene)acetonitrile solution;2-(tributylphosphoranylidene)acetonitrile;cyanomethylenetri-n-butylphosphorane90+%n;CynoMethylenetributyl phosphorane;2-(tributyl-l5-phosphanylidene)acetonitrile;CYANOMETHYLENETRIBUTYLPHOSPHORANE
CAS:157141-27-0
MF:C14H28NP
MW:241.35
EINECS:
Product Categories:pharmacetical;Tsunoda Reagent (Mitsunobu Reaction);Condensation & Active Esterification;Mitsunobu Reaction;Synthetic Organic Chemistry;s
Mol File:157141-27-0.mol
CYANOMETHYLENETRIBUTYLPHOSPHORANE Structure
CYANOMETHYLENETRIBUTYLPHOSPHORANE Chemical Properties
Boiling point 339.1±25.0 °C(Predicted)
density 0.921 g/mL at 25 °C
refractive index n20/D1.500(lit.)
Fp 7 °C
storage temp. 2-8°C
form clear liquid
color Yellow to Amber to Dark purple
InChIKeyOZMLUMPWPFZWTP-UHFFFAOYSA-N
Safety Information
Hazard Codes F,Xn
Risk Statements 10-23/24/25-67-65-48/20-38-11-63
Safety Statements 16-26-36/37/39-62-36/37
RIDADR 3275
WGK Germany 3
HS Code 2931499090
MSDS Information
CYANOMETHYLENETRIBUTYLPHOSPHORANE Usage And Synthesis
Uses(Tributylphosphoranylidene)acetonitrile can be utilized as a reagent in the:
  • Stereoselective synthesis of skytanthine and other O- and N-containing heterocycles by Mitsunobu intramolecular cycloalkylation.
  • Wittig olefination of esters, lactones, N-Boc lactam, and cyclic imide to corresponding Wittig products.

General Description(Tributylphosphoranylidene)acetonitrile is a stabilized trialkylphosphorane that can act as a substitute to the diethyl azodicarboxylate and triphenylphosphine (DEAD-TPP) system for Mitsunobu reaction between nucleophiles (HA) and alcohols (ROH) to form RA. It is highly useful when the pKa of the nucleophiles are higher than 11.
CYANOMETHYLENETRIBUTYLPHOSPHORANE Preparation Products And Raw materials
Raw materialsn-Butyllithium-->Benzene-->Hexane-->Nitromethane-->Chloroacetonitrile-->Tributylphosphine
N,N'-Diisopropylcarbodiimide CYANOMETHYLENETRIBUTYLPHOSPHORANE

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