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Merck
CN

280429

(Triphenylphosphoranylidene)acetonitrile

97%

Synonym(s):

(Cyano)(triphenylphosphoranylidene)methane, (Cyanomethylene)triphenylphosphorane, Cyanomethyltriphenylphosphonium ylide, NSC 135204

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About This Item

Linear Formula:
(C6H5)3P=CHCN
CAS Number:
Molecular Weight:
301.32
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352002
EC Number:
240-689-7
MDL number:
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Product Name

(Triphenylphosphoranylidene)acetonitrile, 97%

InChI key

APISVOVOJVZIBA-UHFFFAOYSA-N

InChI

1S/C20H16NP/c21-16-17-22(18-10-4-1-5-11-18,19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-15,17H

SMILES string

N#CC=P(c1ccccc1)(c2ccccc2)c3ccccc3

assay

97%

reaction suitability

reaction type: C-C Bond Formation

mp

189-195 °C (lit.)

functional group

nitrile
phosphine

Quality Level

Application

Reactant for
  • Preparation of antitrypanosomal activity
  • Direct Michael addition of alkenes
  • Synthesis of 1,6-enynes
  • Beta-umpolung addition of nucleophiles to activated disubstituted alkyl allenes
  • Stereoselective analysis of β-homoproline derivatives
  • Stereoselective olefination of N-sulfonyl imines
  • Palladacycle mediated synthesis of cyano-functionalized chiral diphosphines
  • Horner-Wadsworth-Emmons reactions
Wittig reagent for the preparation of α,β, unsaturated nitriles from carbonyl compounds.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Hiroaki Ohno et al.
The Journal of organic chemistry, 72(12), 4378-4389 (2007-05-11)
Thermal [2 + 2] cycloaddition of allenes with an additional multiple bond is described. By simply heating the allenenes or allenynes having a three-atom tether in an appropriate solvent such as dioxane or DMF, the distal double bond of the

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