539-44-6

Basic information

• Product Name: p-tolyl-hydrazin
• Synonyms: (4-methylphenyl)-hydrazin;4-Tolylhydrazine;p-tolyl-hydrazin
• CAS NO: 539-44-6
• Molecular Formula: C₇H₁₀N₂
• Molecular Weight: 122.1677
• EINECS: 208-717-2
• Mol File: 539-44-6.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 242.8 °C at 760 mmHg
• Flash Point: 115.3 °C
• Appearance: /
• Density: 1.087 g/cm³
• Vapor Pressure: 0.0333mmHg at 25°C
• CAS DataBase Reference: p-tolyl-hydrazin(CAS DataBase Reference)
• NIST Chemistry Reference: p-tolyl-hydrazin(539-44-6)
• EPA Substance Registry System: p-tolyl-hydrazin(539-44-6)

Safety Data

• Statements: R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36:Wear suitable prot
• Hazardous Substances Data: 539-44-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
P-tolyl-hydrazine is utilized as a key intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Production:
p-tolyl-hydrazin serves as a crucial component in the production of agrochemicals, playing a significant role in the creation of pesticides and other agricultural products to protect crops and enhance yields.
Used in Dye and Pigment Manufacturing:
P-tolyl-hydrazine is employed as a raw material in the manufacture of dyes and pigments, contributing to the coloration and quality of various products in different industries.
Used in Organic Compound Synthesis:
Beyond its applications in pharmaceuticals, agrochemicals, dyes, and pigments, p-tolyl-hydrazine is also used in the synthesis of other organic compounds, highlighting its versatility in the chemical industry.

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

Upstream product

• 108-88-3 toluene 
• 1972-28-7 diethylazodicarboxylate 
• 106-49-0 p-toluidine 
• 64-17-5 ethanol 
• 622-74-2 N-phenyl-N'-p-tolyl-triazene 
• 39479-55-5 sulfinyl-p-tolyl-hydrazine 
• 7647-01-0 hydrogenchloride 
• 2028-84-4 p-methylbenzenediazonium chloride 
• 7664-93-9 sulfuric acid 
• 21988-82-9 4-oxo-3-p-tolyl-4,5-dihydro-[1,2,3]thiadiazolium betaine 
• 53464-34-9 p-CH₃C₆H₄NNN(C₂H₅)C₆H₅ 
• 100-46-9 benzylamine 
• 637-60-5 p-tolylhydrazine hydrochloride 
• 106-43-4 para-chlorotoluene 

Downstream Products

• 35496-19-6 3-methyl-1-(4'-methylphenyl)-5-pyrazolone 
• 4870-23-9 2-p-toluidino-isoindoline-1,3-dione 
• 109310-97-6 phthalic acid mono-(N'-p-tolyl-hydrazide) 
• 103394-72-5 3-hydroxy-propionic acid-(N'-p-tolyl-hydrazide) 
• 109670-78-2 cyclohepta[b]quinoxalin-8-one-p-tolylhydrazone 
• 63039-87-2 3-methyl-12H-benzo[4,5]thieno[2,3-a]carbazole 
• 40887-65-8 ethyl 2-(4-methylphenyl)hydrazinecarboxylate 
• 61700-79-6 N'-(4-methylphenyl)acetohydrazide 
• 860253-09-4 N-p-tolyl-N'-trityl-hydrazine 
• 1858-99-7 benzaldehyde p-tolylhydrazone 
• 5705-16-8 N-benzyl-N-(p-methylphenyl)hydrazine 
• 21900-68-5 4-phenyl-1-p-tolyl semicarbazide 
• 1026922-54-2 2-(p-methylphenyl)-4-phenylthiosemicarbazide 
• 38577-24-1 formic acid-(N'-p-tolyl-hydrazide) 

Relevant articles and documents

Cross-Coupling between Hydrazine and Aryl Halides with Hydroxide Base at Low Loadings of Palladium by Rate-Determining Deprotonation of Bound Hydrazine

Reported here is the Pd-catalyzed C–N coupling of hydrazine with (hetero)aryl chlorides and bromides to form aryl hydrazines with catalyst loadings as low as 100 ppm of Pd and KOH as base. Mechanistic studies revealed two catalyst resting states: an arylpalladium(II) hydroxide and arylpalladium(II) chloride. These compounds are present in two interconnected catalytic cycles and react with hydrazine and base or hydrazine alone to give the product. The selectivity of the hydroxide complex with hydrazine to form aryl over diaryl hydrazine was lower than that of the chloride complex, as well as the catalytic reaction. In contrast, the selectivity of the chloride complex closely matched that of the catalytic reaction, indicating that the aryl hydrazine is derived from this complex. Kinetic studies showed that the coupling process occurs by rate-limiting deprotonation of a hydrazine-bound arylpalladium(II) chloride complex to give an arylpalladium(II) hydrazido complex.

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.

Synthesis method of oxalyl hydrazine ligands and application of oxalyl hydrazine ligands in C-N bond coupling reaction

The invention belongs to the technical field of organic chemical synthesis, and particularly relates to a synthesis method of oxalyl hydrazine ligands and application of the oxalyl hydrazine ligands to C-N coupling reaction. The invention provides a method for synthesizing oxalyl hydrazine ligands by taking hydrazine compounds and oxalyl chloride as raw materials. The method has the advantages that the raw materials are easy to obtain, the operation is simple, the post-treatment is easy, and the method is suitable for industrial large-scale production; furthermore, coupling of aryl iodide andhydrazine hydrate is realized by utilizing oxalyl hydrazine ligands, and aryl hydrazine is synthesized. The method is mild in reaction condition, safe, efficient and suitable for industrial production.

1, 3, 4-oxadiazole hydrazide compound as well as preparation method and application thereof

The invention relates to a 1, 3, 4-oxadiazole hydrazide compound as well as a preparation method and application thereof. The compound has a structure as shown in a general formula (I), according to the invention, the method includes taking a 1, 3, 4-oxadiazole compound as a basis and introducing hydrazide into the system; the compound has a good inhibition effect on plant pathogenic bacteria, fungi and oomycetes, and has a good inhibition effect on pathogenic bacteria such as rice bacterial leaf blight, wheat scab, pepper fusarium wilt, sclerotinia sclerotiorum, colletotrichum gloeosporioides, phytophthora infestans, blueberry root rot and the like.

Preparation method of 4-methyl phenylhydrazine hydrochloride

The invention relates to a preparation method of 4-methyl phenylhydrazine hydrochloride. 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 is 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 processis 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 isgreater than or equal to 39%, and the demand on 4-methyl phenylhydrazine hydrochloride in the market is fully met.

Preparation method of 4-methyl phenylhydrazine oxalate

The invention relates to a preparation method of 4-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 99.2%), the yield is greater than or equal to 42%, and the demand on 4-methyl phenylhydrazine oxalate in the market is fully met.

Preparation method of 4-methyl phenylhydrazine phosphate

The invention relates to a preparation method of 4-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 4-methyl phenylhydrazine phosphate in the market is fully met.

Lewis Acid Catalyzed Annulation of Cyclopropane Carbaldehydes and Aryl Hydrazines: Construction of Tetrahydropyridazines and Application Toward a One-Pot Synthesis of Hexahydropyrrolo[1,2- b]pyridazines

In this report, a facile synthesis of tetrahydropyridazines via a Lewis acid catalyzed annulation reaction of cyclopropane carbaldehydes and aryl hydrazines has been demonstrated. Moreover, the generated tetrahydropyridazine further participated in a cycloaddition reaction with donor-acceptor cyclopropanes to furnish hexahydropyrrolo[1,2-b]pyridazines. We also performed these two steps in one pot in a consecutive manner. In addition, a monodecarboxylation reaction of hexahydropyrrolo[1,2-b]pyridazine was achieved with a good yield.

Diaza [1,4] Wittig-type rearrangement of N-allylic-N-Boc-hydrazines into γ-amino- N -Boc-enamines

Diaza [1,4] Wittig-type rearrangement of N-allylic-N-Boc-hydrazines into γ-amino-N-Boc-enamines was demonstrated. The scope and limitation, experimental mechanistic studies, and a proposed reaction mechanism were also described.

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.