827571-80-2

Basic information

• Product Name: 3-chloro-4-Methylaniline
• CAS NO: 827571-80-2
• Molecular Formula: C7H8ClN
• Molecular Weight: 141.59812
• Mol File: 827571-80-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-chloro-4-Methylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-chloro-4-Methylaniline(827571-80-2)
• EPA Substance Registry System: 3-chloro-4-Methylaniline(827571-80-2)

Safety Data

• Hazardous Substances Data: 827571-80-2(Hazardous Substances Data)

Upstream product

• 7647-01-0 hydrogenchloride 
• 121-86-8 2-chloro-4-nitrotoluene 
• 6819-41-6 sodium n-propoxide 
• 71-43-2 benzene 
• 141-52-6 sodium ethanolate 
• 64-17-5 ethanol 
• 89794-02-5 4-bromo-2-chlorotoluene 
• 71-55-6 1,1,1-trichloroethane 
• 106-49-0 p-toluidine 
• 88-51-7 6-amino-4-chloro-meta-toluenesulfonic acid 
• 7006-52-2 3-chloro-N-methylaniline 
• 99-99-0 1-methyl-4-nitrobenzene 
• 95-49-8 2-methylchlorobenzene 
• 15545-48-9 N-(3-chloro-4-methylphenyl)-N,N-dimethylurea 

Downstream Products

• 27085-88-7 3-chloro-N,N-bis-(2-hydroxy-ethyl)-4-methyl-aniline 
• 104176-82-1 N-(5-{4-[4-(3-chloro-4-methyl-phenyl)-piperazino]-phenoxy}-pentyl)-phthalimide 
• 13181-59-4 N'-(3-Chloro-4-methyl-phenyl)-N,N-dimethyl-formamidine 
• 23452-73-5 1-(3-chloro-4-methyl-anilino)-3-prop-2-ynyloxy-propan-2-ol 
• 18237-89-3 α-(3-Chlor-4-methyl-anilino)-α-oximino-aceton 
• 4067-64-5 3-chloro-N-(1,1-dimethyl-prop-2-ynyl)-4-methyl-aniline 
• 7017-25-6 α,β-Dichlor-isobuttersaeure-(3-chlor-4-methyl-anilid) 
• 57729-99-4 (3-Chloro-4-methyl-phenyl)-(2,4-dinitro-6-trifluoromethyl-phenyl)-amine 
• 16939-33-6 3-Nitro-p-toluolsulfon-N-(3-chlor-p-tolyl)-amid 
• 67440-70-4 (1S,2S)-N-(3-Chloro-4-methyl-phenyl)-N',N'-dimethyl-cyclopentane-1,2-diamine 
• 56459-44-0 C₁₄H₂₂ClN₂O₃PS 
• 18800-45-8 3-chloro-4-methylbenzenethiol 
• 57666-53-2 5-(3-Chloro-4-methyl-phenyl)-furan-2-carbaldehyde 
• 96722-64-4 C₁₀H₁₀Cl₂N₂O₂ 

Relevant articles and documents

The influence of different solvents on 2-ammonio-4-chloro-5- methylbenzenesulfonate, including its De- and resulfonation

The title compound (2-ammonio-4-chloro-5-methylbenzenesulfonate), C 7H8ClNO3S, 1, is an intermediate in the synthesis of laked red and yellow azo pigments. Heating 1 in 2-picoline, quinoline and N,N′-dimethylacetamide (DMAc) [or N-methyl-2-pyrrolidone (NMP)] resulted in the formation of three different compounds: a 2-picolinium hydrate (2), a quinolinium quinoline solvate (3), and a sulfate of the desulfonated title compound (4). The three new compounds were structurally characterised using single-crystal diffraction data and chemically using thermal analysis (DTA/TGA), elemental analysis and spectroscopic methods (IR and NMR). By heating 2, 3 and 4 in the solid state, compound 1 is obtained again. In the case of 4, this corresponds to a desulfonation-resulfonation reaction in subsequent steps, which is rarely observed as such. Graphical Abstract: The title compound 2-ammonio-4-chloro-5-methylbenzenesulfonate was heated in 2-picoline, quinoline and N,N′-dimethylacetamide (DMAc) resulting in the formation of three different compounds: a 2-picolinium hydrate (2), a quinolinium quinoline solvate (3), and a sulfate of the desulfonated title compound (4 see Figure). Heating 2, 3 and 4 in the solid state, compound 1 is obtained again. In the case of 4, this corresponds to a desulfonation- resulfonation reaction in subsequent steps, which is rarely observed as such.[Figure not available: see fulltext.]

Direct Superacid-Promoted Difluoroethylation of Aromatics

Under superacid conditions, aromatic amines are directly and regioselectively 1,1-difluoroethylated. Low temperature in situ NMR studies confirmed the presence of benzylic α-fluoronium and α-chloronium ions as key intermediates in the reaction. This method has a wide substrate scope and can be applied to the late-stage functionalization of natural alkaloids and active pharmaceutical ingredients.

AMINATION AND HYDROXYLATION OF ARYLMETAL COMPOUNDS

In one aspect, the present disclosure provides methods of preparing a primary or secondary amine and hydroxylated aromatic compounds. In some embodiments, the aromatic compound may be unsubstituted, substituted, or contain one or more heteroatoms within the rings of the aromatic compound. The methods described herein may be carried out without the need for transition metal catalysts or harsh reaction conditions.

Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds

Arylmetals are highly valuable carbon nucleophiles that are readily and inexpensively prepared from aryl halides or arenes and widely used on both laboratory and industrial scales to react directly with a wide range of electrophiles. Although C-C bond formation has been a staple of organic synthesis, the direct transfer of primary amino (-NH2) and hydroxyl (-OH) groups to arylmetals in a scalable and environmentally friendly fashion remains a formidable synthetic challenge because of the absence of suitable heteroatom-transfer reagents. Here, we demonstrate the use of bench-stable N-H and N-alkyl oxaziridines derived from readily available terpenoid scaffolds as efficient multifunctional reagents for the direct primary amination and hydroxylation of structurally diverse aryl- and heteroarylmetals. This practical and scalable method provides one-step synthetic access to primary anilines and phenols at low temperature and avoids the use of transition-metal catalysts, ligands and additives, nitrogen-protecting groups, excess reagents and harsh workup conditions.

Copper-Based Intermetallic Electride Catalyst for Chemoselective Hydrogenation Reactions

The development of transition metal intermetallic compounds, in which active sites are incorporated in lattice frameworks, has great potential for modulating the local structure and the electronic properties of active sites, and enhancing the catalytic activity and stability. Here we report that a new copper-based intermetallic electride catalyst, LaCu0.67Si1.33, in which Cu sites activated by anionic electrons with low work function are atomically dispersed in the lattice framework and affords selective hydrogenation of nitroarenes with above 40-times higher turnover frequencies (TOFs up to 5084 h-1) than well-studied metal-loaded catalysts. Kinetic analysis utilizing isotope effect reveals that the cleavage of the H-H bond is the rate-determining step. Surprisingly, the high carrier density and low work function (LWF) properties of LaCu0.67Si1.33 enable the activation of hydrogen molecules with extreme low activation energy (Ea = 14.8 kJ·mol-1). Furthermore, preferential adsorption of nitroarenes via a nitro group is achieved by high oxygen affinity of LaCu0.67Si1.33 surface, resulting in high chemoselectivity. The present efficient catalyst can further trigger the hydrogenation of other oxygen-containing functional groups such as aldehydes and ketones with high activities. These findings demonstrate that the transition metals incorporated in the specific lattice site function as catalytically active centers and surpass the conventional metal-loaded catalysts in activity and stability.

Hexafluoro-2-propanol-assisted quick and chemoselective nitro reduction using iron powder as catalyst under mild conditions

Hexafluoro-2-propanol as the promoter for the quick nitro reduction using a combination of iron powder and 2 N HCl aqueous solution is reported. This methodology has several positive features, as it is of room temperature, remarkably short reaction time. A wide range of substrates including those bearing reducible functional groups such as aldehyde, ketone, acid, ester, amide, nitrile, halogens, even allyl, propargyl and heterocycles are chemoselectively reduced in good to excellent yields, even on gram scale. Notably, the highly selective reduction of 3-nitrophenylboronic acid is achieved quantitatively. The reduction is also tolerant of common protecting groups, and aliphatic nitro compound, 1-nitrooctane can be reduced successfully.

Under the conditions of a solvent-free method of hydrogenation to synthesize haloarylamine

The invention provides a method for synthesising halogenated aromatic amine through hydrogenation in a solvent-free condition. The method comprises the following step of: carrying out a liquid-phase hydrogenation reaction on the halogenated aromatic nitro compound shown in formula (I) under the action of hydrogen, in the absence of a solvent and a dehalogenation inhibitor under the action of a carbon-supported large-particle-size precious metal catalyst to prepare the halogenated aromatic amine shown in formula (II). The method provided by the invention is capable of achieving the effect of inhibiting a hydrogenation dehalogenation side reaction in the case of not adding a dehalogenation inhibitor, is high in target product selectivity, and is capable of remarkably increasing the reaction speed.

Hydrogenation of azides over copper nanoparticle surface using ammonium formate in water

Aryl azides undergo clean reduction by copper nanoparticles and ammonium formate in water. The surface hydrogen on copper nanoparticles is considered to be the active reducing species. A variety of functionalized aryl azides and aryl sulfonyl azides are reduced by this procedure to the corresponding amines with excellent chemoselectivity in high yields.

Ecofriendly solvent free microwave enhanced alkyl migration in N-alkyl anilines in dry media conditions

A rapid, cleaner, cost effective and ecofriendly synthesis of exclusive para alkyl anilines in solvent free conditions using solid supports under microwave irradiation is achieved.

Analogues of camptothecin, their use as medicaments and the pharmaceutical compositions containing them

A compound of the formula wherein the substituents are defined as in the specification which compounds are useful in the treatment of cancer.