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Phosphorane, [[(4-methylphenyl)sulfonyl]methylene]triphenyl-, also known as (4-methylphenyl)sulfonyl(methylene)triphenylphosphorane, is a phosphorus-containing organic compound with the chemical formula C25H21OPS. It is a colorless crystalline solid that is soluble in organic solvents. Phosphorane, [[(4-methylphenyl)sulfonyl]methylene]triphenyl- is a phosphorus ylide, which is a type of phosphorus-stabilized carbanion, and it is widely used in organic synthesis as a reagent for the Wittig reaction, a method for the synthesis of alkenes. The structure of this phosphorane consists of a central phosphorus atom bonded to three phenyl groups and a (4-methylphenyl)sulfonyl group, with a double bond to a methylene (CH2) group. Its unique structure and reactivity make it a valuable tool in the preparation of various organic compounds, particularly in the formation of carbon-carbon double bonds.

5554-81-4

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5554-81-4 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 5554-81-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,5,5 and 4 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 5554-81:
(6*5)+(5*5)+(4*5)+(3*4)+(2*8)+(1*1)=104
104 % 10 = 4
So 5554-81-4 is a valid CAS Registry Number.

5554-81-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name (4-methylphenyl)sulfonylmethylidene-triphenyl-λ<sup>5</sup>-phosphane

1.2 Other means of identification

Product number -
Other names Tolylsulfonylmethylenetriphenylphosphorane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5554-81-4 SDS

5554-81-4Relevant academic research and scientific papers

Comparison of free-radical inhibiting antioxidant properties of carvedilol and its phenolic metabolites

Malig, Thomas C.,Ashkin, Mitchell R.,Burman, Austin L.,Barday, Manuel,Heyne, Belinda J. M.,Back, Thomas G.

, p. 606 - 615 (2017/03/30)

Carvedilol is a widely prescribed drug for the treatment of heart failure and the prevention of associated ventricular arrhythmias. It has also been reported to function as a biological antioxidant via hydrogen atom transfer from its carbazole N-H moiety

Using Ylide Functionalization to Stabilize Boron Cations

Scherpf, Thorsten,Feichtner, Kai-Stephan,Gessner, Viktoria H.

supporting information, p. 3275 - 3279 (2017/03/17)

The metalated ylide YNa [Y=(Ph3PCSO2Tol)?] was employed as X,L-donor ligand for the preparation of a series of boron cations. Treatment of the bis-ylide functionalized borane Y2BH with different trityl salts or B(C6F5)3 for hydride abstraction readily results in the formation of the bis-ylide functionalized boron cation [Y?B?Y]+ (2). The high donor capacity of the ylide ligands allowed the isolation of the cationic species and its characterization in solution as well as in solid state. DFT calculations demonstrate that the cation is efficiently stabilized through electrostatic effects as well as π-donation from the ylide ligands, which results in its high stability. Despite the high stability of 2 [Y?B?Y]+ serves as viable source for the preparation of further borenium cations of type Y2B+←LB by addition of Lewis bases such as amines and amides. Primary and secondary amines react to tris(amino)boranes via N?H activation across the B?C bond.

Bridging the Gap between Bisylides and Methandiides: Isolation, Reactivity, and Electronic Structure of an Yldiide

Scherpf, Thorsten,Wirth, Regina,Molitor, Sebastian,Feichtner, Kai-Stephan,Gessner, Viktoria H.

supporting information, p. 8542 - 8546 (2015/11/27)

Bisylides and methandiides are two unique families of carbon bases that have found a variety of applications in recent years. Metalated ylides (yldiides) are the link between these types of compounds. Yet, only little is known about their properties, reactivities, and particularly their electronic structure. Here, we report the preparation of the metalated ylide [Ph3P-C-SO2Tol]- (1) with different alkali metal counterions. The compounds have been studied by X-ray diffraction analysis and NMR spectroscopy and the first structures of a sodium and potassium yldiide are presented. The electronic structure of 1 was explored by DFT calculations confirming its relation with other divalent carbon species. Reactivity studies demonstrate the strong nucleophilicity of the yldiide and its capability to act both as a σ- and π-donor. Metalation makes a difference. The metalation of a stabilized phosphorus ylide yields the isolable yldiide [Ph3P-C-SO2Tol]-, which was isolated with different alkali metal counterions. Its electronic structure shows a clear relation to other divalent carbon species such as bisylides. Reactivity studies demonstrate the strong nucleophilicity of the yldiide and its capability to act both as a σ- and π-donor.

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