74404-33-4

Basic information

• Product Name: (2-ETHYL-6-METHYLPHENYL)HYDRAZINE HYDROCHLORIDE
• Synonyms: (2-ETHYL-6-METHYLPHENYL)HYDRAZINE HYDROCHLORIDE;1-(2-ETHYL-6-METHYLPHENYL)HYDRAZINE HYDROCHLORIDE;1-(2-Ethyl-6-methylphenyl)hydrazine, HCl
• CAS NO: 74404-33-4
• Molecular Formula: C₉H₁₄N₂*ClH
• Molecular Weight: 186.68
• Mol File: 74404-33-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: (2-ETHYL-6-METHYLPHENYL)HYDRAZINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (2-ETHYL-6-METHYLPHENYL)HYDRAZINE HYDROCHLORIDE(74404-33-4)
• EPA Substance Registry System: (2-ETHYL-6-METHYLPHENYL)HYDRAZINE HYDROCHLORIDE(74404-33-4)

Safety Data

• Hazardous Substances Data: 74404-33-4(Hazardous Substances Data)

Usage

General Description

(2-ethyl-6-methylphenyl)hydrazine hydrochloride is a chemical compound that is typically used in organic synthesis and pharmaceutical research. It is a hydrazine derivative, which means it contains a nitrogen-nitrogen bond. (2-ETHYL-6-METHYLPHENYL)HYDRAZINE HYDROCHLORIDE has properties that make it suitable for a variety of chemical reactions and processes, and it is often used as a reagent in the synthesis of organic compounds. Additionally, it may also have potential applications in the development of new pharmaceutical drugs or as a precursor to other chemical compounds. However, it is important to handle this compound with caution, as hydrazine derivatives can be toxic and hazardous if not handled properly.

Upstream product

• 24549-06-2 6-ethyl-o-toluidine 

Downstream Products

• 132370-93-5 N-{2,2,2-Trichloro-1-[N'-(2-ethyl-6-methyl-phenyl)-hydrazino]-ethyl}-formamide 
• 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 
• 132370-74-2 (E)-2,3-Dichloro-4-[(2-ethyl-6-methyl-phenyl)-hydrazono]-but-2-enoic acid 
• 132370-79-7 2-(2'-ethyl-6'-methylphenyl)-4,5-dichloro-2,3-dihydropyridazin-3-one 
• 132370-77-5 (E)-2,3-Dibromo-4-[(2-ethyl-6-methyl-phenyl)-hydrazono]-but-2-enoic acid 
• 132370-84-4 3-Bromo-1-(2-ethyl-6-methyl-phenylamino)-pyrrole-2,5-dione 
• 132370-81-1 (E)-3-[N'-(2-Ethyl-6-methyl-phenyl)-hydrazinocarbonyl]-acrylic acid 

Relevant articles and documents

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.

"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.