21136-32-3

Usage

Chemical compound

Yes

Use

Key intermediate in the synthesis of organic compounds

Potential biological activity

Yes

Studied for

Anti-cancer agent

Ability

Inhibits the growth of cancer cells

Investigated for

Treatment of neurological disorders

Research suggestion

Neuroprotective properties

Unique structure

Yes

Subject of study

Pharmaceutical and chemical industries

InChI:InChI=1/C21H20N2/c1-4-10-19(11-5-1)16-22-23(17-20-12-6-2-7-13-20)18-21-14-8-3-9-15-21/h1-16H,17-18H2

Upstream product

• 5336-53-8 dibenzylnitrosamine 
• 100-52-7 benzaldehyde 
• 5802-60-8 N,N-dibenzylhydrazine 
• 64-17-5 ethanol 
• 64-19-7 acetic acid 
• 103-49-1 dibenzylamine 
• 26254-04-6 N,N'-dibenzyl-hydrazine; hydrochloride 
• 17352-65-7 tribenzyl-hydrazine; hydrochloride 
• 1194-66-7 2,6-dichloronitrosobenzene 
• 104-88-1 4-chlorobenzaldehyde 
• 7626-68-8 N,N'-dibenzylhydrazine 

Downstream Products

• 65111-78-6 tribenzyl-hydrazine 
• 5416-62-6 tetrabenzyl-hydrazine 
• 36750-88-6 1-phenyl-3,3,3-trifluoro-1,2-propanedione 
• 20698-90-2 (R)-3,3,3-Trifluoro-2-hydroxy-2-phenyl-propionic acid methyl ester 
• 20445-31-2 R-(+)-α-trifluoromethyl-α-methoxy-phenylacetic acid 

Relevant academic research and scientific papers

Oxidation of 1,1-Disubstituted Hydrazines to Tetrazenes with Benzeneseleninic Acid

The oxidation of 1,1-disubstituted hydrazines with benzeneseleninic acid in methanol affords the corresponding tetrazenes in high yield.

Visible Light-Induced [3+2] Cyclization Reactions of Hydrazones with Hypervalent Iodine Diazo Reagents for the Synthesis of 1-Amino-1,2,3-Triazoles

In this study, visible-light-induced [3+2] cyclization reactions of hydrazones with hypervalent iodine diazo reagents as diazomethyl radical precursors are reported. Mild reaction conditions, a broad substrate scope, and excellent functional group compatibility were observed. Furthermore, the synthetic utility was demonstrated by gram-scale synthesis and elaboration to several value-added products. This protocol broadens the scope of diazo chemistry, and is applicable to the late-stage functionalization of natural products. (Figure presented.).

Visible-light-enabled C(sp2)-H difluoroalkylation of aldehyde-derived hydrazones under metal-free conditions

A Eosin Y-catalyzed C(sp2)-H difluoromethylation of aldehyde-derived hydrazones between difluoroalkyl bromides and aldehyde-derived hydrazones is reported. This reaction has a wide range of substrates and occurs under metal-free condition. A me

Extending the Scope of the B(C6F5)3-Catalyzed C=N Bond Reduction: Hydrogenation of Oxime Ethers and Hydrazones

The B(C6F5)3-catalyzed hydrogenation is applied to aldoxime triisopropylsilyl ethers and hydrazones bearing an easily removable phthaloyl protective group. The C=N reduction of aldehyde-derived substrates (oxime ethers and hydrazones) is enabled by using 1,4-dioxane as the solvent known to participate as the Lewis-basic component in FLP-type heterolytic dihydrogen splitting. More basic ketone-derived hydrazones act as Lewis bases themselves in the FLP-type dihydrogen activation and are therefore successfully hydrogenated in nondonating toluene. The difference in reactivity between aldehyde- and ketone-derived substrates is also reflected in the required catalyst loading and dihydrogen pressure.

Asymmetric 1,2-Perfluoroalkyl Migration: Easy Access to Enantioenriched α-Hydroxy-α-perfluoroalkyl Esters

This study has led to the development of a novel, highly efficient, 1,2-perfluoro-alkyl/-aryl migration process in reactions of hydrate of 1-perfluoro-alkyl/-aryl-1,2-diketones with alcohols, which are promoted by a Zn(II)/bisoxazoline and form α-perfluoro-alkyl/-aryl-substituted α-hydroxy esters. With (-)-8-phenylmenthol as the alcohol, the corresponding menthol esters are generated in high yields with excellent levels of diastereoselectivity. The mechanistic studies show that the benzilic ester-type rearrangement reaction takes place via an unusual 1,2-migration of electron-deficient trifluoromethyl group rather than the phenyl group. The overall process serves as a novel, efficient, and simple approach for the synthesis of highly enantioenriched, biologically relevant α-hydroxy-α-perfluoroalkyl carboxylic acid derivatives.

OXIDATION OF HYDRAZINES WITH CARBON TETRACHLORIDE

Some hydrazines, especially 1,2-dialkylhydrazines are oxidized to the corresponding diazenes (azo compounds) by carbon tetrachloride presumably via nucleophilic attack by nitrogen on chlorine.Monacylhydrazines are converted to the corresponding diacylhydrazines.

OXIDATION OF HYDRAZINES WITH NITROSOBENZENES

Nitrosoarenes react with 1,1-disubstituted hydrazines to yield products of direct oxidation and the thermally stable triazene N-oxides.The triazene N-oxides undergo photoinduced fragmentation to yield products which may be rationalized through the interme

Reaction of Aromatic Aldehydes with 1,2-Dibenzylhydrazine

The reactions of 1,2-dibenzylhydrazine with several aromatic aldehydes in refluxing toluene gave the benzaldehyde dibenzylhydrazones (9) and (13) in high yield.It is suggested from labelling studies and from the failure to trap an azomethine imine in the

Oxidation of 1,1-disubstituted hydrazines with benzeneseleninic acid and selenium dioxide. Facile preparation of tetrazenes

Various 1,1-disubstituted hydrazines were oxidized with benzeneseleninic acid in methanol, generally producing the corresponding tetrazenes in high yield.Studies of the by-products of the reaction, of the effects of protic vs. aprotic solvents, and trapping experiments suggest that N-aminonitrenes are unlikely intermediates in this oxidation.An alternative mechanism involving a Pummerer-like reaction of seleninamides derived from the hydrazines is proposed.Tetrazene formation fails when the hydrazine precursor contains an aryl or p-toluenesulfonyl substiuent, or when it is highly hindered.Selenium dioxide may be employed as the oxidant instead of the seleninic acid, but is generally less efficacious in achieving high tetrazene yields.