76527-75-8

Usage

Uses

Used in Organic Synthesis:
N-[(DIPHENYLPHOSPHINYL)METHYL]-N-METHYLANILINE is used as a ligand in organic synthesis for transition metal catalysis, facilitating the formation of carbon-carbon and carbon-heteroatom bonds. Its unique properties make it a valuable component in various chemical reactions.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-[(DIPHENYLPHOSPHINYL)METHYL]-N-METHYLANILINE is used as a building block for the synthesis of complex organic molecules. Its potential applications in this field are attributed to its ability to form stable complexes with transition metals, which can be utilized in the development of new drugs.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, N-[(DIPHENYLPHOSPHINYL)METHYL]-N-METHYLANILINE is employed as a precursor for the synthesis of complex organic molecules. Its role in creating stable metal complexes can contribute to the development of new agrochemicals with improved properties and efficacy.

InChI:InChI=1/C20H20NOP/c1-21(18-11-5-2-6-12-18)17-23(22,19-13-7-3-8-14-19)20-15-9-4-10-16-20/h2-16H,17H2,1H3

Upstream product

• 13657-45-9 N-methyl-N-(methoxymethyl)-aniline 
• 1079-66-9 chloro-diphenylphosphine 
• 207291-40-5 N-(ethoxyymethyl)-N-methylbenzamine 
• 100-61-8 N-methylaniline 
• 62-53-3 aniline 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 5469-96-5 N-(2,2-diphenyl-vinyl)-N-methyl-aniline 
• 76527-53-2 cyclohexylidene(N-methylanilino)methane 
• 76527-66-7 1-[(Diphenyl-phosphinoyl)-(methyl-phenyl-amino)-methyl]-cyclohexanol 
• 76527-59-8 (Z)-1-(N-methylanilino)-2-phenylpropene 
• 76527-58-7 (E)-1-(N-methylanilino)-2-phenylpropene 
• 76527-60-1 (2-Ethyl-but-1-enyl)-methyl-phenyl-amine 
• 76527-62-3 (Z)-2-methyl-1-(N-methylanilino)-1-butene 
• 76527-61-2 (E)-2-methyl-1-(N-methylanilino)-1-butene 
• 76527-57-6 cycloheptylidene(N-methylanilino)methane 
• 875-30-9 1,3-dimethylindole 
• 51206-77-0 3-(4-methoxyphenyl)-1-methyl-1H-indole 
• 30020-98-5 N-methyl-3-phenylindole 
• 25076-84-0 1-(N-Methyl-N-phenylamino)-2-methyl-1-propene 
• 76527-56-5 2-(N-Methylanilinomethylene)adamantane 

Relevant academic research and scientific papers

Organic photoredox catalytic α-C(sp3)-H phosphorylation of saturated: Aza -heterocycles

A metal-free C(sp3)-H phosphorylation of saturated aza-heterocycles via the merger of organic photoredox and Br?nsted acid catalyses was established under mild conditions. This protocol provided straightforward and economic access to a variety of valuable α-phosphoryl cyclic amines by using commercially available diarylphosphine oxide reagents. In addition, the D-A fluorescent molecule DCQ was used for the first time as a photocatalyst and exhibited an excellent photoredox catalytic efficiency in this transformation. A series of mechanistic experiments and DFT calculations demonstrated that this transformation underwent a sequential visible light photoredox catalytic oxidation/nucleophilic addition process.

Synthesis of isotopically labelled L-phenylalanine and L-tyrosine

A synthetic route to stable-isotope-substituted L-phenylalanine is presented, which allows the introduction of 13C, 15N, and deuterium labels at any position or combination of positions. For labelling of the aromatic ring, a synthetic route to ethyl benzoate (or benzonitrile) has been developed, based on the electrocyclic ring-closure of a 1,6-disubstituted hexatriene system, with in situ aromatization by elimination of one (amino) substituent. Several important (highly isotopically enriched) synthons have been prepared, namely benzonitrile, benzaldehyde, ethyl benzoate, and ethyl diphenyloxyacetate. Labelled L-phenylalanines have been synthesized from both aromatic precursors by initial conversion into sodium phenylpyruvate and subsequent transformation of this intermediate into the L-α-amino acid by an enzymatic reductive amination reaction. In this manner, highly enriched phenylalanines are obtained on the 10-gram scale and with high enantiomeric purities (≥ 99% ee). The method has been validated by the synthesis of [1'13C]-L-Phe and [2-D]-L-Phe. In addition, two methods are described for the introduction of isotopes into L-tyrosine starting from the isotopically enriched precursors benzonitrile and ethyl benzoate.

A New Access to 3-(2'-Aminovinyl)indoles and Their First Diels-Alder Reactions

3-Acylindoles react with α-amino-α'-diphenylphosphinoyl-substituted carboanions to 3-(2'-aminovinyl)indoles (7 and 12) via carbinols.The electron-rich 3-vinylindoles 7 and 12 undergo Diels-Alder reactions with N-phenylmaleimide.

A New Access to 2'-Amino-substituted Vinylindoles as Donor-activated Heterocyclic Dienes and their First Diels-Alder Reactions

Reactions of the 3-acylindoles 5, 10, and 15 with α-amino-α'-diphenylphosphinoyl-substituted carbanions gave rise to the 2'-amino-substituted 3- and 2-vinylindoles 7, 12, and 17 by way of the isolable carbinols 6, 11, and 16.The heterocyclic dienes 7, 12,

Synthesis of indoles using (N-arylaminomethyl)diphenylphosphine oxides

A new route for the synthesis of 1,3-disubstituted indoles, based on (N-arylaminomethyl)-diphenylphosphine oxide (1) chemistry, is described.Adducts 2, obtained by addition of the carbanions from 1 to aldehydes, were treated with p-toluenesulfonic acid to form the desired indoles 4 in good yields, without isolation of the intermediate amino ketones 3.

The synthesis of α-amino-substituted diphenylphosphine oxides

Four methods with differing but overlapping specificity are described for the synthesis of α-unsubstituted as well as α-substituted (aminomethyl)diphenylphosphine oxides.The first method is based on the Arbusov reaction, the second on a Mannich-type condensation of diphenylphosphine oxide with aldehydes and secondary amines, the third on the addition of Ph2P(O)H to enamines and the fourth on the reaction of anions derived from α-unsubstituted (aminomethyl)diphenylphosphine oxides with various electrophiles.

N-NETHYL-N-ANILINOMETHYL DIPHENYLPHOSPHINE OXIDE: A VERSATILE REAGENT FOR THE SYNTHESIS OF ENAMINES

Cyclic as well as acyclic ketones, both saturated and α,β-unsatorated, can be converted into their homologous enamines by Horner-Wittig reaction with N-methyl-N-anilinomethyl diphenylphosphine oxide (3).