536-89-0

Usage

Uses

Used in Pharmaceutical Industry:
M-TOLYLHYDRAZINE is used as a pharmaceutical intermediate for the synthesis of various drugs and active pharmaceutical ingredients. It serves as a crucial component in the production of certain medications due to its ability to react with other compounds, such as cyclohexanone, to form 7-methyl-1,2,3,4-tetrahydro-carbazole, which has potential applications in the development of new therapeutic agents.

InChI:InChI=1/C7H10N2/c1-6-3-2-4-7(5-6)9-8/h2-5,9H,8H2,1H3

Upstream product

• 63815-25-8 3-methylbenzene diazonium 
• 2028-72-0 m-toluenediazonium chloride 
• 108-44-1 1-amino-3-methylbenzene 
• 7647-01-0 hydrogenchloride 
• 625-95-6 3-Iodotoluene 
• 591-17-3 meta-bromotoluene 
• 108-41-8 1-chloro-3-methylbenzene 

Downstream Products

• 35496-20-9 5-methyl-2-m-tolyl-1,2-dihydro-pyrazol-3-one 
• 112252-48-9 propionic acid-(N'-m-tolyl-hydrazide) 
• 62698-28-6 benzaldehyde m-tolylhydrazone 
• 860756-87-2 2-(m-methylphenyl)-4-phenylthiosemicarbazide 
• 21364-10-3 diphenyl-acetic acid-(N'-m-tolyl-hydrazide) 
• 6463-31-6 3-Amino-1-m-tolyl-2-pyrazoline 
• 52722-67-5 α-(N'-m-tolyl-hydrazino)-isobutyronitrile 
• 76869-99-3 3-m-tolyl-carbazic acid methyl ester 
• 6243-74-9 acetone-m-tolylhydrazone 
• 54381-25-8 2-methylpropanoic acid 2-(3-methylphenyl)hydrazide 

Relevant academic research and scientific papers

Visible-light-mediated phosphonylation reaction: formation of phosphonates from alkyl/arylhydrazines and trialkylphosphites using zinc phthalocyanine

In this work, we developed a ligand- and base-free visible-light-mediated protocol for the photoredox syntheses of arylphosphonates and, for the first time, alkyl phosphonates. Zinc phthalocyanine-photocatalyzed Csp2-P and Csp3-P bond formations were efficiently achieved by reacting aryl/alkylhydrazines with trialkylphosphites in the presence of air serving as an abundant oxidant. The reaction conditions tolerated a wide variety of functional groups.

Preparation method of 3-methyl phenylhydrazine phosphate

The invention relates to a preparation method of 3-methyl phenylhydrazine phosphate. The preparation method comprises the following steps: diazotization, reduction, purification and salt formation. Inthe diazotization and reduction steps, reaction liquid is kept with high acidity by means of concentrated hydrochloric acid, so that the reaction is smoothly and fully carried out. In the reduction step, zinc powder-concentrated hydrochloric acid is taken as a reducing agent to replace sodium thiosulfate, sodium hydrogen sulfite, stannous chloride-hydrochloric and the like, the reducing propertyis good, the yield is high, the reaction time is shortened, impurities such as zinc hydroxide generated by the reaction are conveniently removed, and the product is few in impurity and high in purity.In the salt formation step, acetone is used to wash, so that the purity of the product is improved, and the appearance of the product is ensured. According to the preparation method, the process is stable and reliable, the operation is easy, the product purity is high (the content of the product detected by high performance liquid chromatography is greater than or equal to 99.2%), the yield is greater than or equal to 42%, and the demand on 3-methyl phenylhydrazine phosphate in the market is fully met.

Preparation method of 3-methyl phenylhydrazine oxalate

The invention relates to a preparation method of 3-methyl phenylhydrazine oxalate. The preparation method comprises the following steps: diazotization, reduction, purification and salt formation. In the diazotization and reduction steps, reaction liquid is kept with high acidity by means of concentrated hydrochloric acid, so that the reaction is smoothly and fully carried out. In the reduction step, zinc powder-concentrated hydrochloric acid is taken as a reducing agent to replace sodium thiosulfate, sodium hydrogen sulfite, stannous chloride-hydrochloric and the like, the reducing property isgood, the yield is high, the reaction time is shortened, impurities such as zinc hydroxide generated by the reaction are conveniently removed, and the product is few in impurity and high in purity. In the salt formation step, acetone is used to wash, so that the purity of the product is improved, and the appearance of the product is ensured. According to the preparation method, the process is stable and reliable, the operation is easy, the product purity is high (the content of the product detected by high performance liquid chromatography is greater than or equal to 99%), the yield is greater than or equal to 42%, and the demand on 3-methyl phenylhydrazine oxalate in the market is fully met.

Diversification of edaravone via palladium-catalyzed hydrazine cross-coupling: Applications against protein misfolding and oligomerization of beta-amyloid

N-Aryl derivatives of edaravone were identified as potentially effective small molecule inhibitors of tau and beta-amyloid aggregation in the context of developing disease-modifying therapeutics for Alzheimer's disease (AD). Palladium-catalyzed hydrazine monoarylation protocols were then employed as an expedient means of preparing a focused library of 21 edaravone derivatives featuring varied N-aryl substitution, thereby enabling structure-activity relationship (SAR) studies. On the basis of data obtained from two functional biochemical assays examining the effect of edaravone derivatives on both fibril and oligomer formation, it was determined that derivatives featuring an N-biaryl motif were four-fold more potent than edaravone.

Remazol-Catalyzed Hydroperoxyarylation of Styrenes

A mild photocatalytic hydroperoxyarylation of styrenes has been developed, in which a novel photocatalyst, remazol brilliant blue R (RBBR), is employed at low catalytic loading (1 mol%). The operationally easy procedure uses air as the dioxygen source. Simple mono-substituted styrenes react with aryl hydrazines in moderate-to-good yields. RBBR is proposed to act as a photosensitizer for the generation of singlet oxygen.

Efficient synthesis of aryl hydrazines using copper-catalyzed cross-coupling of aryl halides with hydrazine in PEG-400

An efficient and convenient method for the synthesis of aryl hydrazines is described via copper-catalyzed cross-coupling of aryl halides with aqueous hydrazine in PEG-400. This protocol is applicable to both electron-deficient and electron-rich aryl iodides and bromides, and even to sterically hindered substrates, giving aryl hydrazines in good to excellent yields.

MECHANISM OF THE FISCHER INDOLE SYNTHESIS. QUANTUM-CHEMICAL INTERPRETATION OF THE REARRANGEMENT OF SUBSTITUTED CYCLOHEXANONE ARYLHYDRAZONES TO TETRAHYDROCARBAZOLES

Calculations of a number of model structures within the scheme of Fischer indole synthesis were made on the basis of a bonding variant of perturbation theory in the self-consistent-field (SCF) MO LCAO method.A quantum-chemical interpretation of the effect of substituents on the course of the thermal process is given.The kinetics of the thermal and acid-catalyzed indolization of substituted cyclohexanone arylhydrazones to tetrahydrocarbazoles were studied by spectrophotometry.It was shown that the experimental data are in satisfactory agreement with the calculated values. It was concluded that a concerted mechanism ( a -sigma-tropic shift) for the step involving the formation of a carbon-carbon bond in the Fischer reaction is preferred.

Carbazole methyl malonates

A process for the preparation of α-methyl-carbazole-2-acetic acids, which comprises reacting an α-methyl-3-oxocyclohexane malonic acid di-lower alkyl ester with a substituted phenylhydrazine, and thereafter sequentially oxidizing and hydrolyzing the reaction product to obtain the desired acid, is described.