95-81-8

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-5-methylaniline is used as a key intermediate in the synthesis and preparation of acylthiourea derivatives. These derivatives have potential applications as anti-viral agents, particularly against vaccinia and La Crosse viruses. 2-Chloro-5-methylaniline plays a crucial role in the development of new therapeutic agents to combat viral infections.

InChI:InChI=1/C7H8ClN/c1-5-2-3-6(8)7(9)4-5/h2-4H,9H2,1H3

Upstream product

• 620-25-7 N-(3-methylphenyl)hydroxylamine 
• 75-15-0 carbon disulfide 
• 7791-25-5 sulfuryl dichloride 
• 537-92-8 3-Methylacetanilide 
• 1228378-19-5 2-azido-N-(2-chloro-5-methylphenyl)-N-methyl-2-phenylacetamide 
• 89-60-1 1-chloro-4-methyl-2-nitro-benzene 
• 6819-41-6 sodium n-propoxide 
• 71-43-2 benzene 

Downstream Products

• 104296-69-7 (2-chloro-5-methyl-phenyl)-carbamic acid-(4-chloro-but-2-ynyl ester) 
• 18931-83-4 N-(2-chloro-5-methylphenyl)acetamide 
• 22261-57-0 bis(2-amino-4-methylphenyl) disulfide 
• 4387-32-0 2-chloro-5-methyl-benzonitrile 
• 260046-15-9 (2-chloro-5-methyl-phenyl)-(2-chloro-pyrimidin-4-yl)-amine 
• 18474-59-4 6-methyl-1H-indole-2-carboxylic acid 
• 21303-50-4 2-mercapto-5-methyl benzothiazole 
• 922510-92-7 1-(2-chloro-5-methylphenyl)hydrazine hydrochloride 
• 1228378-03-7 N-(2-chloro-5-methylphenyl)-2-oxo-2-phenylacetamide 
• 1257524-26-7 C₂₄H₂₂ClN₃O₂S 
• 1257524-27-8 C₂₄H₂₂ClN₃O₂S 
• 1257524-28-9 C₂₄H₂₂ClN₃O₂S 
• 1257524-29-0 C₂₃H₁₉Cl₂N₃O₂S 
• 57729-78-9 2-(2-chloro-5-methylanilino)-3,5-dinitrobenzotrifluoride 

Relevant academic research and scientific papers

Industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles-catalyzed hydrogenation of nitroarenes

The development of green and efficient methods for hydrogenation of nitroarenes is still highly demanding in organic synthesis. Herein, we report an industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles process for the synthesis of aryl amines with good yields via hydrogenation of nitroarenes. Nine key anti-cancer drug intermediates were successfully achieved with protocol. And Osimertinib intermediate 4m can be smoothly synthesized at a 2.67 kg-scale with >99.5% HPLC purity. This protocol features cheap carbon source, highly catalytic activity, simple operation, kilogram-scalable and recyclable catalysts (eight times without observable losing activity).

Synthesis and antileishmanial evaluation of thiazole orange analogs

Cyanine compounds have previously shown excellent in vitro and promising in vivo antileishmanial efficacy, but the potential toxicity of these agents is a concern. A series of 22 analogs of thiazole orange ((Z)-1-methyl-4-((3-methylbenzo[d]thiazol-2(3H)-ylidene)methyl)quinolin-1-ium salt), a commercial cyanine dye with antileishmanial activity, were synthesized in an effort to increase the selectivity of such compounds while maintaining efficacy. Cyanines possessing substitutions on the quinolinium ring system displayed potency against Leishmania donovani axenic amastigotes that differed little from the parent compound (IC50 12–42 nM), while ring disjunction analogs were both less potent and less toxic. Changes in DNA melting temperature were modest when synthetic oligonucleotides were incubated with selected analogs (ΔTm ≤ 5 °C), with ring disjunction analogs showing the least effect on this parameter. Despite the high antileishmanial potency of the target compounds, their toxicity and relatively flat SAR suggests that further information regarding the target(s) of these molecules is needed to aid their development as antileishmanials.

N,S co-doped hierarchically porous carbon materials for efficient metal-free catalysis

Metal-free carbon catalysts with excellent catalytic performance have drawn much research attention recently. Herein, polymer-derived N,S co-doped carbon catalysts (PDNSC-X) with a hierarchically porous structure were facilely prepared by a cost-effective and convenient strategy via carbonization of a N- and S atom-containing polymer precursor and were subsequently used as efficient metal-free catalysts. The catalytic activity of the as-fabricated PDNSC-800 was greater than those of other reported heteroatom-doped carbon catalysts in catalytic reduction of various nitroarenes. The high catalytic activity of PDNSC-800 was related to the synergistic effects of a high surface area, a hierarchically porous structure, abundant N- and S-containing active sites, and defect formation. In addition, the close relationship between the N species (especially pyrrolic N) and high selectivity in metal-free catalytic synthesis was investigated in the reduction of nitroarenes and selective oxidation of ethylbenzene. This study may provide a new strategy to fabricate specific heteroatom-doped metal-free carbon catalysts for environmentally friendly efficient organic transformation.

Co-MOF-Derived Hierarchical Mesoporous Yolk-shell-structured Nanoreactor for the Catalytic Reduction of Nitroarenes with Hydrazine Hydrate

Porous nanoreactors demonstrate immense potential for applications in heterogeneous catalysis due to their excellent mass-transfer performance and stability. The design of a simple, universal strategy for fabricating nanoreactor catalysts is of significance for organic transformation. In this study, a nanoreactor with a hierarchical mesoporous yolk-shell structure was successfully prepared by the high-temperature carbonization of a ZIF-67@polymer composite. The core of the resultant Co@ZDC@mC material comprised Co NPs anchored in the ZIF-67-derived carbon framework, while the shell comprised resin-polymer-derived mesoporous carbon. The as-obtained Co@ZDC@mC-700 catalyst enriched reactants, efficiently catalyzed the reaction in the core, and permitted the desorption of the product from the nanoreactor. In the catalytic reduction of nitrobenzene with N2H4?H2O, Co@ZDC@mC-700 exhibited superior catalytic efficiency (TOF=1136.3 h?1). In addition, Co@ZDC@mC-700 exhibited excellent performance for the catalytic reduction of various functionalized nitroarenes, as well as good reusability and recyclability. Hence, a simple, useful approach for fabricating a metal-organic-framework-derived non-noble metal-based yolk-shell nanoreactor for effective catalytic transformation is proposed.

A Co2B Mediated NaBH4 Reduction Protocol Applicable to a Selection of Functional Groups in Organic Synthesis

A high-yielding and high-rate reduction method that operates with alkenes, alkynes, azides, nitriles, and nitroarenes was developed and optimized. The method makes use of sodium borohydride reduction of CoSO4 under release of hydrogen along with the formation of Co2B as a nanoparticle material. The produced Co2B activates the various functional groups for hydride reduction. The protocol was proven to operate with an assortment of functional groups to provide good to excellent yields. Furthermore, the reduction method was successfully adapted, implemented, and developed for a continuous flow approach using the multi-jet oscillating disk (MJOD) flow reactor platform at atmospheric pressure.

Aminal-based Hypercrosslinked Polymer Modified with Small Palladium Nanoparticles for Efficiently Catalytic Reduction of Nitroarenes

Fabrication of heterogeneous catalysts with excellent activity, selectivity and stability is significant for various catalytic applications. Here, we prepared a hypercrosslinked polymer (HCP) via a facile and cost-effective strategy using ferrocenecarboxaldehyde and melamine as building blocks. Then, the HCP was modified with highly dispersed ultrafine Pd nanoparticles (Pd/HCP). The obtained Pd/HCP shows excellent catalytic activity in the catalytic reduction of nitroarenes under mild reaction conditions. It′s worth mentioning that the N atoms in the HCP can efficiently coordinate Pd ions to form small Pd nanoparticles (NPs) and subsequently prevent the aggregation and leaching of Pd NPs during the reaction, so the Pd/HCP catalyst is highly stable and can be reused at least eight cycles without loss of catalytic activity. Therefore, this work may provide possibilities for using HCPs as ideal supporting materials for fabricating highly stable and efficient heterogeneous catalysts.

Tricyclic Compounds As mPGES-1 Inhibitors

The present invention relates to tricyclic compounds of formula (I) or pharmaceutically acceptable salt thereof as mPGES-1 inhibitors. These compounds are inhibitors of the microsomal prostaglandin E synthase-1 (mPGES-1) enzyme and are therefore useful in the treatment of pain and/or inflammation from a variety of diseases or conditions, such as asthma, osteoarthritis, rheumatoid arthritis, acute or chronic pain and neurodegenerative diseases.

Copper-catalyzed synthesis of azaspirocyclohexadienones from ∝-azido- N -arylamides under an oxygen atmosphere

A copper-catalyzed reaction of ∝-azido-N-arylamides was found to proceed under an oxygen atmosphere to afford azaspirocyclohexadienones. The present transformation is carried out by a sequence of denitrogenative formation of iminyl copper species from ∝-azido-N-arylamides and their imino-cupration with an intramolecular benzene ring on the amido nitrogen followed by consecutive formation of C-O bonds. The preliminary investigation revealed that molecular oxygen is a prerequisite for achieving the present catalytic cyclization and that one of the oxygen atoms of O2 was found to be incorporated into the cyclohexadienone moiety.

Substituted tetrahydro-1H-pyrido[4,3-b]indoles as serotonin receptors agonists and antagonists

The present application describes compounds, including all pharmaceutically acceptable salts, prodrugs, solvates and stereoisomers thereof, according to Formula I, pharmaceutical compositions, comprising at least one compound according to Formula I and optionally at least one additional therapeutic agent and methods of treating various diseases, conditions and disorders associated with modulation of serotonin receptors such as, for example: metabolic diseases, which includes but is not limited to obesity, diabetes, diabetic complications, atherosclerosis, impared glucose tolerance and dyslipidemia; central nervous system diseases which includes but is not limited to, anxiety, depression, obsessive compulsive disorder, panic disorder, psychosis, schizophrenia, sleep disorder, sexual disorder and social phobias; cephalic pain; migraine; and gastrointestinal disorders using compounds according to Formula I

New diamines and a process for their production

New aminoalkyl anilines having the formula: STR1 wherein k is 0 or 1; QNH2 is a residue of formula STR2 which is situated in one of the positions of the benzene ring ortho or para to the amino group and wherein n is an integer from 1 to 15, R1 is C1 -C8 alkyl, R2 is C1 -C4 alkyl or R1 and R2, together with the carbon atom to which they are attached, form a C5 -C8 cycloalkylene residue, R3 is H or C1 -C6 alkyl, C3 -C8 cycloalkyl, or C6 -C10 aryl; and R4 and R5 are H or C1 -C4 alkyl; as well as the corresponding salts of compounds of formula I with organic or inorganic acids and metal salt complexes; process for their production; and their use as intermediates for polyamides.