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280429

Sigma-Aldrich

(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:
16640-68-9
Molecular Weight:
301.32
EC Number:
240-689-7
MDL number:
MFCD00567633
UNSPSC Code:
12352002
PubChem Substance ID:
24856944
NACRES:
NA.22

Quality Level

100

Assay

97%

reaction suitability

reaction type: C-C Bond Formation

mp

189-195 °C (lit.)

functional group

nitrile
phosphine

SMILES string

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

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

InChI key

APISVOVOJVZIBA-UHFFFAOYSA-N

Related Categories

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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Deleterious substance

JAN Code

280429-25G:
280429-VAR:
280429-5G:4548173129419
280429-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCL9593
MKBW9010V
MKBS1787V
MKBJ2622V
MKBC0669V

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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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