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N-(diphenylmethylidene)-N-phenylamine oxide, also known as Michler's ketone, is an organic compound with the chemical formula C19H15NO. It is a yellow crystalline solid that is widely used as a chemical intermediate, particularly in the synthesis of various dyes and pigments. Michler's ketone is known for its ability to form colored compounds upon reaction with primary amines, which is the basis for its use in the production of azo dyes. It is also used as a fluorescent brightening agent in the textile industry and as a reagent in analytical chemistry. The compound is characterized by its distinct chemical structure, featuring a diphenylmethylidene group attached to a phenylamine oxide moiety, which contributes to its unique properties and applications.

4504-13-6

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4504-13-6 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 4504-13-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,5,0 and 4 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 4504-13:
(6*4)+(5*5)+(4*0)+(3*4)+(2*1)+(1*3)=66
66 % 10 = 6
So 4504-13-6 is a valid CAS Registry Number.

4504-13-6Relevant academic research and scientific papers

cis-β-Ruthenium Complexes with Sterically Bulky Salen Ligands: Enantioselective Intermolecular Carbene Insertion into Si-H Bonds and X-ray Crystal Structure of cis-β-[RuII(salen)(CO)(CPh2)] Complex

Lee, Chi Lun,Chen, Daqing,Chang, Xiao-Yong,Tang, Zhou,Che, Chi-Ming

supporting information, p. 2642 - 2652 (2020/07/24)

The synthesis, spectroscopy, crystal structure, and electrochemical behavior of cis-β-RuII(CO)2, cis-β-RuII(CO)(H2O), and cis-β-RuII(CO)(carbene) complexes supported by sterically bulky salen ligands are described, along with the catalytic activity of chi

Coupling of N -Nosylhydrazones with Nitrosoarenes: Transition-Metal-Free Approach to (Z)- N -Arylnitrones

Liu, Tingting,Liu, Zhaohong,Liu, Zhenhua,Hu, Donghua,Wang, Yeming

supporting information, p. 1728 - 1736 (2018/02/14)

An efficient and transition-metal-free protocol for the synthesis of (Z)- N -arylnitrones from the direct coupling of N -nosylhydrazones with nitrosoarenes under mild conditions is described. The protocol is compatible with a wide range of functional groups placed on both the reagents and provided the corresponding nitrones in good to excellent yields by simple recrystallization process. The use of these 1,3-dipoles for the synthesis of substituted indoles is elaborated for 2,3-diphenyl-1 H -indole.

A Protocol to Transform Sulfones into Nitrones and Aldehydes

Rodrigo, Eduardo,Alonso, Inés,Cid, M. Belén

supporting information, (2018/09/27)

A simple method to transform sulfones into nitrones and therefore into the corresponding carbonyl derivatives has been developed. Some examples demonstrate that it is a new reliable and versatile reaction in the toolbox of sulfones that has great synthetic potential. NMR and computational studies were used to elucidate the mechanism.

A Protocol to Transform Sulfones into Nitrones and Aldehydes

Rodrigo, Eduardo,Alonso, Inés,Cid, M. Belén

supporting information, p. 5789 - 5793 (2018/09/29)

A simple method to transform sulfones into nitrones and therefore into the corresponding carbonyl derivatives has been developed. Some examples demonstrate that it is a new reliable and versatile reaction in the toolbox of sulfones that has great synthetic potential. NMR and computational studies were used to elucidate the mechanism.

Synthesis of α,β-Unsaturated N-Aryl Ketonitrones from Oximes and Diaryliodonium Salts: Observation of a Metal-Free N-Arylation Process

Ma, Xiao-Pan,Shi, Wei-Min,Mo, Xue-Ling,Li, Xiao-Hua,Li, Liang-Gui,Pan, Cheng-Xue,Chen, Bo,Su, Gui-Fa,Mo, Dong-Liang

, p. 10098 - 10107 (2015/11/03)

An efficient transition-metal-free method for the preparation of α,β-unsaturated N-aryl ketonitrones under mild conditions has been developed. This reaction shows good functional group tolerance for both electron-rich and electron-deficient substituents on both oximes and diaryliodonium salts. Two examples of gram-scale preparations have been realized in good yields. Further transformations of these nitrones to different N-heterocycles have been demonstrated. DFT calculations suggest that N-arylation products are formed by [1,3]-phenyl migration of an O-coordinated oximate complex via a four-centered transition state, while the O-arylation products are formed by [1,3]-phenyl migration of a N-coordinated oximate complex.

Photochemical reactivity of aromatic and heteroaromatic nitroderivatives in the presence of arylalkenes

D'Auria, Maurizio,Esposito, Vittorio,Mauriello, Giacomo

, p. 14253 - 14272 (2007/10/03)

The irradiation of styrene in the presence of nitroarenes in acetonitrile gives the corresponding nitrones in high yields. However, when 4-methyl-5-ethenylthiazole is used as arylalkene the starting material is converted to a pyrrole analogous of thianthrene. On the contrary, when 1,1-diphenylethylene is used, the main product observed is benzophenone. Nitrones are obtained only as minor products. An unusual coupling product, where a substitution reaction has occurred on the carbon bearing the nitro group, is also obtained. trans-Stilbene is unreactive under the same photochemical conditions, and it gives in low yields only benzaldehyde. Finally, indene gives, when aromatic nitro derivatives are used, only oxidation products, while, when heteroaromatic nitro derivatives are used, only substitution products on the nitro group are observed. The above described reactivity can be explained by using the results of AM1 semiempirical calculations on the frontier orbitals of the reagents. Both the nature of the LSOMO of the nitroarenes and the dipole moments of the reagents can account for the observed reactivity. The nitrone obtained in the photochemical reaction between styrene and nitrobenzene is used as starting material in a 1,3-dipolar cycloaddition reaction with styrene.

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