24006-21-1

Basic information

• Product Name: N-methyl-N-(4-methylphenyl)hydrazine
• CAS NO: 24006-21-1
• Molecular Weight: 136.197
• Mol File: 24006-21-1.mol

Chemical Properties

• CAS DataBase Reference: N-methyl-N-(4-methylphenyl)hydrazine(CAS DataBase Reference)
• NIST Chemistry Reference: N-methyl-N-(4-methylphenyl)hydrazine(24006-21-1)
• EPA Substance Registry System: N-methyl-N-(4-methylphenyl)hydrazine(24006-21-1)

Safety Data

• Hazardous Substances Data: 24006-21-1(Hazardous Substances Data)

Usage

Uses

Used in Research and Development:
4-MMPH is used as a chemical intermediate for the synthesis of various organic compounds in research and development. Its role in the creation of new compounds makes it a valuable asset in the field of organic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-MMPH is used as a building block for the development of new drugs. Its unique chemical properties allow it to be a key component in the synthesis of potential therapeutic agents.
Used in Chemical Synthesis:
4-MMPH is utilized in the chemical synthesis of various compounds for different applications, such as agrochemicals, dyes, and other specialty chemicals. Its versatility in synthesis contributes to its importance in the chemical industry.

Upstream product

• 2028-84-4 p-methylbenzenediazonium chloride 
• 539-44-6 N-4-methylphenylhydrazine 
• 74-88-4 methyl iodide 
• 937-24-6 N-methyl-N-nitroso-p-toluidine 
• 7440-66-6 zinc 
• 94542-53-7 10-p-Tolylazo-[9]anthrol 
• 623-08-5 N-methyl-p-toluidine 
• 60-29-7 diethyl ether 
• 7697-37-2 nitric acid 
• 7664-93-9 sulfuric acid 
• 136984-61-7 (E)-3-(p-tolylhydrazono)-2-butanone 

Downstream Products

• 86809-06-5 6,6,6-Trifluoro-2,2-dimethyl-5-(methyl-p-tolyl-hydrazono)-hexan-3-one 
• 26190-49-8 1,4-Bis-(p-methylphenyl)-1,4-dimethyl-2-tetrazen 
• 26190-53-4 1.4-Dimethyl-1-(4'-tolyl)-4-(p-carbaethoxyphenyl)-2-tetrazen 
• 26190-51-2 1.4-Dimethyl-1.4-bis(4-carbaethoxyphenyl)-2-tetrazen 
• 113407-50-4 4-Chloro-butyric acid N'-methyl-N'-p-tolyl-hydrazide 
• 100726-24-7 6-methyl-3-phenylbenzo[e][1,2,4]triazine 
• 1416897-77-2 (E)-methyl 3-(5-methyl-2-(methylamino)phenyl)acrylate 
• 36362-82-0 1,5-dimethyl-2,3-diphenyl-1H-indole 
• 947595-94-0 [Ti(NN(Me)(4-CH3C6H4))(4,4'-di-tert-butyl-2,2'-bipyridine)(N,N-di(pyrrolyl-α-methyl)-N-methylamine)] 
• 30724-66-4 N,N’-dimethyl-bis(4-methylphenyl)hydrazine 
• 74763-67-0 4-(N,N'-Dimethyl-N'-p-tolyl-hydrazino)-benzoic acid ethyl ester 
• 74763-68-1 diethyl 4,4′-(methylenebis(azanediyl))dibenzoate 
• 10541-82-9 ethyl 4-(methylamino)benzoate 
• 623-08-5 N-methyl-p-toluidine 

Relevant articles and documents

Cobalt-Catalyzed, Directed Intermolecular C-H Bond Functionalization for Multiheteroatom Heterocycle Synthesis: The Case of Benzotriazine

Transition-metal-catalyzed, directed intermolecular C-H bond functionalization is synthetically useful but heavily underexplored in multiheteroatom heterocycle synthesis. Herein we report a cobalt catalytic method for the formation of a three-nitrogen-bearing benzotriazine scaffold via the coupling of arylhydrazine and oxadiazolone. This synthetic protocol features a low-cost base metal catalyst, a maximum number of heteroatoms built into a heterocycle, a distinct synthetic logic for benzotriazines, a superior step economy, and a broad substrate scope.

Rh(iii)-catalyzed, hydrazine-directed C-H functionalization with 1-alkynylcyclobutanols: A new strategy for 1: H -indazoles

Rh(iii)-catalyzed coupling of phenylhydrazines with 1-alkynylcyclobutanols was realized through a hydrazine-directed C-H functionalization pathway. This [4+1] annulation, based on the cleavage of a Csp-Csp triple bond in alkynylcyclobutanol, provides a new pathway to prepare diverse 1H-indazoles under mild reaction conditions. This journal is

A Versatile, Traceless C-H Activation-Based Approach for the Synthesis of Heterocycles

A versatile, traceless C-H activation-based approach for the synthesis of diversified heterocycles is reported. Rh(III)-catalyzed, N-amino-directed C-H alkenylation generates either olefination products or indoles (in situ annulation) in an atom- and step-economic manner at room temperature. The remarkable reactivity endowed by this directing group enables scale-up of the reaction to a 10 g scale at a very low catalyst loading (0.01 mol %/0.1 mol %). Ex situ annulation of olefination product provides entry into an array of heterocycles.

Ruthenium(II)-Catalyzed Traceless C?H Functionalization Using an N?N Bond as an Internal Oxidant

A previously elusive RuII-catalyzed N?N bond-based traceless C?H functionalization strategy is reported. An N-amino (i.e., hydrazine) group is used for the directed C?H functionalization with either an alkyne or an alkene, affording an indole derivative or olefination product. The synthesis features a broad substrate scope, superior atom and step economy, as well as mild reaction conditions.

AMIDE DERIVATIVES AND DRUGS

The present invention provides an amide derivative represented by the following formula [1]: wherein n represents 0 or 1; X represents CR4 or N; Y represents CR6 or N; Z represents CR7 or N; R1 and R2 may be the same or different and each represents hydrogen, optionally substituted alkyl, acyl, optionally substituted aryl, or an optionally substituted aromatic heterocyclic group; R4, R5, R6 and R7 may be the same or different and each represents hydrogen, halogen, hydroxy, amino, alkyl, haloalkyl, alkoxy, monoalkylamino, dialkylamino, arylalkyl, cyano, or nitro; and R3 represents optionally substituted alkylamino, optionally substituted arylamino, or optionally substituted cyclic amino, or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition comprising them as an active ingredient. The compound of the present invention is useful as a TGF-β inhibitor.

MEDICINAL COMPOSITION

The present invention is composed of a pharmaceutical composition for the therapy of nephritis which comprises an amide derivative represented by the following formula [1] or pharmaceutically acceptable salt thereof, as an active ingredient: ???wherein R1 and R2 may be the same or different and each is hydrogen, alkyl which may be substituted, acyl, aryl which may be substituted, or an aromatic heterocyclic group which may be substituted; R3, R4, R5 and R6 may be the same or different and each is hydrogen, halogen, hydroxy, amino which may be substituted, alkyl which may be substituted, alkoxy or nitro and the like; and R7 represents cyclic amino which may be substituted or azabicycloalkylamino which may be substituted. The pharmaceutical composition of the invention is useful for the therapy of nephritis.

AMIDE DERIVATIVES AND DRUG COMPOSITIONS

The present invention is composed of an amide derivative represented by the following formula [1] or pharmaceutically acceptable salt thereof: ???wherein R1 and R2 may be the same or different and each is hydrogen, alkyl which may be substituted, acyl, aryl which may be substituted, or an aromatic heterocyclic group which may be substituted; R3, R4, R5, and R6 may be the same or different and each is hydrogen, halogen, hydroxy, amino which may be substituted, alkyl which may be substituted, alkoxy, or nitro and the like; and R7 represents cyclic amino which may be substituted or azabicycloalkylamino which may be substituted, and a pharmaceutical composition which comprises it as an active ingredient. The compound of the invention is useful as an inhibitor of TGF-β production or an antagonist of TGF-β.

Structures of reactive nitrenium ions: Time-resolved infrared laser flash photolysis and computational studies of substituted N-methyl-N-arylnitrenium ions

A series of para-substituted N-methyl-N-phenylnitrenium ions (N-(4-biphenylyl)-N-methylnitrenium ion, N-(4-chlorophenyl)-N-methylnitrenium ion, N-(4-methoxyphenyl)-N-methylnitrenium ion, and N-(4-methylphenyl)-N-methylnitrenium ion) were generated through photolysis of the appropriately substituted 1-aminopyridinium salt. Laser flash photolysis using UV - vis detection as well as photoproduct analysis verified that the expected nitrenium ions were formed cleanly and rapidly following photolysis. Laser flash photolysis with time-resolved infrared detection allowed for structural characterization of the nitrenium ions through observation of a symmetrical aromatic C=C stretch in the region 1580-1628 cm-1. The specific frequencies reflect the degree of quinoidal character present in each phenylnitrenium ion (i.e., the degree to which the nitrenium ion resembles a 4-iminocyclohexa-2,5-dienyl cation). The 4-methoxy derivative shows the highest frequency C=C stretch, indicating that this strongly π-electron-donating substituent imparts more quinoidal character, and the 4-chloro derivative shows the lowest frequency C=C stretch, suggesting that it possesses the least quinoidal character. Quantum calculations using density functional theory (BPW91/cc-pVDZ) were carried out on the same nitrenium ions. The theoretically derived IR frequencies showed excellent quantitative agreement with the experiment. The computed structures show significant bond length alternation in the phenyl rings, shortened C-N bond lengths, and substantial positive charge delocalization into the phenyl rings. All of these effects are more pronounced with increasing π-donating character of the ring substituent. Arylnitrenium ions are well described as 4-iminocyclohexa-2,5-dienyl cations.

SIMPLE PREPARATION OF N-ALKYL-N-ARYLHYDRAZINES FROM DIAZOTABLE N-ARYLAMINES

Phase-Transfer-catalyzed N-alkylation of arylhydrazones 2, followed by hydrazinolysis with hydrazine hydrate in the presence of concentrated hydrochloric acid, provides a new access to N-alkyl-N-arylhydrazines 3.

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.