74404-33-4

Usage

Uses

Used in Organic Synthesis:
(2-Ethyl-6-methylphenyl)hydrazine hydrochloride is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, contributing to the formation of a wide array of organic compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (2-Ethyl-6-methylphenyl)hydrazine hydrochloride is utilized in research for its potential applications in the development of new pharmaceutical drugs. Its unique structure and reactivity make it a valuable component in the creation of novel medicinal agents.
Used as a Precursor in Chemical Compounds:
(2-Ethyl-6-methylphenyl)hydrazine hydrochloride also serves as a precursor to other chemical compounds, playing a crucial role in the synthesis of more complex molecules that may have specific applications in various fields.

Upstream product

• 24549-06-2 6-ethyl-o-toluidine 

Downstream Products

• 132370-84-4 3-Bromo-1-(2-ethyl-6-methyl-phenylamino)-pyrrole-2,5-dione 
• 132370-87-7 3,4-Dichloro-1-(2-ethyl-6-methyl-phenylamino)-pyrrole-2,5-dione 
• 132370-77-5 (E)-2,3-Dibromo-4-[(2-ethyl-6-methyl-phenyl)-hydrazono]-but-2-enoic acid 
• 74404-34-5 2-ethyl-6-methylphenylhydrazine 
• 132370-79-7 2-(2'-ethyl-6'-methylphenyl)-4,5-dichloro-2,3-dihydropyridazin-3-one 
• 132370-74-2 (E)-2,3-Dichloro-4-[(2-ethyl-6-methyl-phenyl)-hydrazono]-but-2-enoic acid 
• 63075-50-3 cyclohexanone 2-ethyl-6-methylphenylhydrazone 
• 1616514-83-0 1-(2-ethyl-6-methylphenyl)-2-(4-nitrophenyl)diazene 
• 1616514-73-8 3′-ethyl-5′-methyl-5-trifluoromethyl-1,1′-biphenyl-2,4′-diamine 
• 1616514-79-4 3-ethyl-5-methyl-N¹-[4-(trifluoromethyl)phenyl]benzene-1,4-diamine 
• 1616514-85-2 1-(2-ethyl-6-methylphenyl)-2-(4-(trifluoromethyl)phenyl)diazene 
• 1616514-65-8 tert-butyl 2-(2-ethyl-6-methylphenyl)-1-(4-(trifluoromethyl)phenyl)hydrazinecarboxylate 
• 1616514-62-5 tert-butyl 2-(2-ethyl-6-methylphenyl)-1-(4-nitrophenyl)hydrazinecarboxylate 
• 1639128-65-6 N'-Boc-N-(2-ethyl-6-methylphenyl)hydrazine 

Relevant academic research and scientific papers

Regioselectivity of the ortho- and para-semidine, and diphenyline rearrangements

The regioselectivity of the o-semidine, p-semidine, and diphenyline rearrangements of unsymmetrical N,N′-diarylhydrazines was studied experimentally. The results indicate that their electron-rich nitrogen atom is first protonated and then the electron-poor non-protonated nitrogen atom undergoes an N[1,3]-sigmatropic shift to the ortho-position of the electron-rich aryl rings, generating key intermediates. The intermediates can undergo (1) a direct proton transfer to give o-semidines, (2) a second N[1,3]-shift of the electron-poor nitrogen atom and then proton transfer to furnish p-semidines, and (3) a [3,3]-sigmatropic shift and subsequent proton transfer to yield diphenylines. It is the first N[1,3]-sigmatropic shift step that plays an important role in controlling the regioselectivity in the three rearrangements, further determining the structures of o-semidines, p-semidines, and diphenylines. The current results provide new insights into the o/p-semidine and diphenyline rearrangements and useful information for controlling and predicting the structures of the rearrangement products.

Design, synthesis, crystal structures, and insecticidal activities of eight-membered azabridge neonicotinoid analogues

Three series of novel azabridge neonicotinoid analogues were designed and synthesized, which were constructed by starting material A, glutaraldehyde, and primary amine hydrochlorides (aliphatic amines, phenylhydrazines, and anilines). Most of the eight-membered azabridge compounds presented higher insecticidal activities than oxabridged compound B against cowpea aphid (Aphis craccivora) and brown planthopper (Nilaparvata lugens). Compared with imidacloprid, some azabridged compounds exhibited excellent insecticidal activity against brown planthopper. The crystal structures and bioassay indicated that changing bridge atoms from O to N could lead to entirely different conformations, which might be the important influential factor of the bioactivities.

"1,4" Alkyl Migrations in Fischer Indole Cyclizations

The product from Fisher indole cyclization and dehydrogenation of cyclohexanone 2,4,6-trimethylphenylhydrazone (1) was determined to be 2,3,4-trimethylcarbazole (3) resulting from a formal 1,4-methyl migration, as previously proposed.To determine the destinations of migrating groups in these rearrangements, the Fischer indole cyclization and dehydrogenation of cyclohexanone 2-ethyl-6-methylphenylhydrazone (17) were studied.The products obtained were 1-ethylcarbazole, 1-methylcarbazole, 2-ethyl-1-methylcarbazole (18), and an apparent mixture of 1-ethyl-4-methylcarbazole (21) and 4-ethyl-1-methylcarbazole (22).However, no 1-ethyl-2-methylcarbazole (19), which would have been obtained by a "1,4"-methyl migration, was obtained.Analysis of the product ratios suggested that the apparent ethyl shift in formation of 18 actually proceeded by a formal shift of either an ethyl or a methyl group, followed by a ethyl shift.Cyclization of 3-pentanone 2,4,6-trimethylphenylhydrazone (26) proceeded to give the product of "1,4" methyl migration, demonstrating that such reactions can occur with phenylhydrazones of ketones other than cyclohexanone.It is proposed that steric factors play a major role in determining whether migrating groups undergo or "1,4" shifts during Fischer indole cyclizations.