634-91-3

Usage

Uses

Used in Pharmaceutical Industry:
3,4,5-Trichloroaniline is used as a building block for the synthesis of novel 3,4-dihydroisoquinoline compounds, which have been identified as potential antidepressant agents. Its role in the development of new pharmaceuticals highlights its importance in the field of medicinal chemistry.
Used in Chemical Research:
As a useful building block, 3,4,5-Trichloroaniline is also employed in chemical research for the preparation of various complex organic molecules. Its isomers, as referenced in the catalogue entries T774090, T774323, and T774025, further expand the scope of its applications in chemical synthesis.
Used in Antileukemic Drug Development:
3,4,5-Trichloroaniline forms triand tetrachloroaniline-Pt(II) complexes, which exhibit good antileukemic activity. This makes it a valuable compound in the development of new drugs for the treatment of leukemia, a type of cancer that affects the blood and bone marrow.

InChI:InChI=1/C6H4Cl3N/c7-4-1-3(10)2-5(8)6(4)9/h1-2H,10H2

Upstream product

• 20098-48-0 3,4,5-trichloronitrobenzen 
• 21928-51-8 5-bromo-1,2,3-trichloro-benzene 

Downstream Products

• 33715-62-7 N-(3,4,5-trichlorophenyl)acetamide 
• 35804-51-4 1-(3,4,5-trichloro-phenyl)-biguanide; hydrochloride 
• 19010-53-8 N-(3,4-dichloro-phenyl)-N'-(3,4,5-trichloro-phenyl)-urea 
• 76393-46-9 N,N'-bis-(3,4,5-trichloro-phenyl)-urea 
• 35754-32-6 1,2,3-trichloro-5-isothiocyanatobenzene 
• 91821-60-2 N,N'-bis-(3,4,5-trichloro-phenyl)-thiourea 
• 86282-83-9 N-(3,4,5-trichloro-phenyl)-anthranilic acid 
• 117367-27-8 N-(3,4,5-Trichlorphenyl)-2-hydroxybenzamid 
• 634-90-2 1,2,3,5-tetrachlorobenzene 
• 609-19-8 3,4,5-trichlorophenol 
• 599-52-0 2,3,4,4,5,6-hexachlorocyclohexa-2,5-dien-1-one 
• 3107-21-9 3,4,5-trichlorofluorobenzene 
• 87-61-6 1,2,3-trichlorobenzene 
• 23742-32-7 Cyclopropan-3,4,5-trichlor-carboxanilid 

Relevant academic research and scientific papers

General and Chemoselective Copper Oxide Catalysts for Hydrogenation Reactions

Copper oxide catalysts have been prepared by pyrolysis of copper acetate on aluminum oxide. The material resulting from pyrolysis at 800 °C allows for catalytic hydrogenations at low temperature of a variety of unsaturated compounds such as quinolines, alkynes, ketones, imines, and polycyclic aromatic hydrocarbons as well as nitroarenes with good activity and selectivity.

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.

Nitrogen-Doped Graphene-Supported Iron Catalyst for Highly Chemoselective Hydrogenation of Nitroarenes

A nitrogen-doped graphene-supported iron catalyst was used for the first time in the hydrogenation of a series of nitroarenes to give the corresponding amines with excellent activity and chemoselectivity under mild reaction conditions. Physicochemical characterization of the catalyst by transmission electron microscopy, X-ray diffraction, X-ray photoelectron spectroscopy, and M?ssbauer spectroscopy revealed the formation of iron particles with an iron oxide core and a metallic iron shell that were coated by a few layers of nitrogen-doped graphene. The unique structure of FeNx/C in the catalyst was proven to contribute to the hydrogenation activity.

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.

USE OF THERMALLY-TREATED SUPPORTED COBALT CATALYSTS COMPRISING A POLYCYCLIC AROMATIC STRUCTURE CONSISTING OF NITROGEN LIGANDS FOR HYROGENATING AROMATIC NITRO COMPOUNDS

The invention relates to the use of thermally-treated supported cobalt catalysts for hydrogenating aromatic nitro compounds, the cobalt catalysts having been prepared by in situ immobilization of a cobalt-amine complex on an inorganic porous support and subsequent pyrolysis, and, in the cobalt-amine complex used, cobalt being present bonded to an aromatic or heterocyclic nitrogen ligand L, the nitrogen ligand being selected so as to form a polyaromatic structure with the cobalt atom.

Reduction of nitroarenes using CO and H2O in the presence of a nanostructured cobalt oxide/Nitrogen-Doped Graphene (NGr) catalyst

The most common route to anilines is based on the reduction of the corresponding nitroarenes. In general, hydrogen is preferred as reducing agent and numerous catalytic systems are known to achieve such transformations. Besides, the use of CO/H2O as hydrogen source offers interesting possibilities for reductions. Carbon monoxide is a cheap and abundant chemical used on industrial scale for a variety of transformations. Although the reduction of nitroarenes with CO/H2O is known in the presence of noble-metal catalysts, earth-abundant inexpensive catalysts showing high selectivity have not yet been developed. In this respect, herein we present the use of a heterogeneous cobalt oxide catalyst (Co3O4/NGr@C), which is modified by nitrogen-doped graphene layers. Using this non-noble metal catalyst nitroarenes are reduced in high yields and good chemoselectivities.

Pinacol as a new green reducing agent: Molybdenum-catalyzed chemoselective reduction of sulfoxides and nitroaromatics

Pinacol is disclosed as a new chemoselective and environmentally benign reducing agent for sulfoxides and nitroaromatics assisted by readily available dichlorodioxomolybdenum(VI) complexes as catalysts. A wide range of substrates including those bearing challenging functional groups has been efficiently and selectively reduced with acetone and water being the only by-products of these reactions. Copyright

Efficient and highly selective iron-catalyzed reduction of nitroarenes

Pyrolysis of iron-phenanthroline complexes supported on carbon leads to highly selective catalysts for the reduction of structurally diverse nitroarenes to anilines in 90-99% yields. Excellent chemoselectivity for the nitro group reduction is demonstrated.

Iron-catalyzed selective reduction of nitroarenes to anilines using organosilanes

The iron-catalyzed reduction of aromatic nitro compounds to the corresponding anilines applying organosilanes is reported. In the presence of FeX2-R3P catalysts a series of nitroarenes is selectively reduced tolerating a wide range of functional groups.

Reductively activated polar" nucleophilic aromatic substitution. IV [1]. Thermal and photochemical behavior of polychloro and polyfluoro-nitrobenzenes in front of soft nucleophiles

The nucleophilic aromatic substitution of pentachloronitrobenzene (PCNB) with benzenethiolate and benzeneselenide anions in aqueous solution give rise to fast nitro group substitution in both cases. In the same conditions, pentafluoronitrobenzene (PFNB) and 3,4,5-trichloronitrobenzene (TCNB) undergo substitution of the halogen atom placed in para position with respect to the nitro group. Mechanistic studies suggest that the reactions of PCNB and PFNB (substitution of very electronegative leaving groups) follow a mechanism that includes a "polar" attack of the nucleophile on the aromatic substrate in the first step and a fast "radical" evolution of the o-complex intermediate. On the other hand, the chloride substitution in the TCNB reactions follows the classical SNAr mechanism. The photochemical reactions of PCNB, PFNB and TCNB in the presence of nucleophiles (electron donors) lead in all cases to photoreduction products (anilines) probably through the aromatic radical anion. Springer-Verlag 1996.