| Identification | Back Directory | [Name]
CYANOMETHYLENETRIBUTYLPHOSPHORANE | [CAS]
157141-27-0 | [Synonyms]
CMBP
Tsunoda Reagent
Cyanomethyltributylphosphorane
CynoMethylenetributyl phosphorane
CYANOMETHYLENETRIBUTYLPHOSPHORANE
CYANOMETHYLENETRI-N-BUTYLPHOSPHORANE
Cyanomethylenetributylphosphorane>
(Tributylphosphoranylidene)acetonitrile
2-(tributylphosphoranylidene)acetonitrile
cyanomethylenetri-n-butylphosphorane90+%n
2-(tributyl-l5-phosphanylidene)acetonitrile
Acetonitrile,2-(tributylphosphoranylidene)-
(Tributylphosphoranylidene)acetonitrile solution
{[Tri(but-1-yl)]phosphoranylidene}acetonitrile 97% | [Molecular Formula]
C14H28NP | [MDL Number]
MFCD01321151 | [MOL File]
157141-27-0.mol | [Molecular Weight]
241.35 |
| Chemical Properties | Back Directory | [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. ]
Refrigerator | [form ]
clear liquid | [color ]
Yellow to Amber to Dark purple | [InChI]
InChI=1S/C14H28NP/c1-4-7-11-16(14-10-15,12-8-5-2)13-9-6-3/h14H,4-9,11-13H2,1-3H3 | [InChIKey]
OZMLUMPWPFZWTP-UHFFFAOYSA-N | [SMILES]
C(#N)C=P(CCCC)(CCCC)CCCC |
| Hazard Information | Back Directory | [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. |
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