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

General Description

P-tolyl-hydrazine is a chemical compound with the formula C7H10N2. It is a colorless to pale yellow liquid with a strong odor, and it is highly flammable. P-tolyl-hydrazine is primarily used in the synthesis of pharmaceuticals and agrochemicals. It is also utilized in the manufacture of dyes, pigments, and other organic compounds. P-tolyl-hydrazine is known to be a hazardous substance, as it may cause skin and eye irritation upon contact, and prolonged exposure can lead to respiratory and nervous system effects. It is important to handle and store p-tolyl-hydrazine with care to prevent any potential health and safety risks.

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

Upstream product

• 2028-84-4 p-methylbenzenediazonium chloride 
• 108-88-3 toluene 
• 1972-28-7 diethylazodicarboxylate 
• 459-44-9 4-methylbenzenediazonium tetrafluoroborate 
• 106-49-0 p-toluidine 
• 4510-12-7 methyl 4-hydrazinobenzoate 
• 64-17-5 ethanol 
• 622-74-2 N-phenyl-N'-p-tolyl-triazene 
• 39479-55-5 sulfinyl-p-tolyl-hydrazine 
• 7647-01-0 hydrogenchloride 
• 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 

Downstream Products

• 35496-19-6 3-methyl-1-(4'-methylphenyl)-5-pyrazolone 
• 34019-60-8 1-(p-tolyl)-1,2-dihydropyridazine-3,6-dione 
• 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 
• 67491-55-8 4-methyl-benzoic acid N'-p-tolyl-hydrazide 
• 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 
• 65763-66-8 1-Benzoyl-2-(4-methylphenyl)hydrazine 

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.

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.

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.