5345-54-0

Usage

Uses

Used in Chemical Synthesis:
3-Chloro-4-methoxyaniline is used as a chemical intermediate for the synthesis of various pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure allows for further functionalization and incorporation into a wide range of compounds.
Used in Analytical Chemistry:
3-Chloro-4-methoxyaniline is utilized as a reference compound in the development and validation of analytical methods, particularly in the field of chromatography and fluorescence detection. Its distinct chemical properties make it a suitable candidate for method optimization and performance evaluation.
Used in Environmental Monitoring:
3-Chloro-4-methoxyaniline can be employed as a target analyte in environmental monitoring studies, where its detection and quantification can provide insights into the presence and distribution of chlorpropham and its metabolites in the environment.
Used in Research and Development:
In the research and development sector, 3-Chloro-4-methoxyaniline serves as a valuable compound for studying the effects of chlorpropham exposure and its potential impact on human health and the environment. It can also be used to explore new applications and develop innovative solutions in various industries.

Upstream product

• 217314-34-6 1-(3-chloro-4-methoxyphenyl)-2,5-dimethyl-1H-pyrrole 
• 19937-59-8 metoxuron 
• 766-51-8 2-Chloroanisole 
• 135050-44-1 3-chloro-4-iodoaniline 
• 1249435-72-0 C₁₀H₁₀ClNO 
• 2267-25-6 2-chloro-4-fluoro-1-methoxy-benzene 
• 119927-90-1 3-chloro-4,4-dimethoxycyclohexa-2,5-dien-1-one 
• 18093-12-4 3-chloro-4-methoxyphenol 
• 108-43-0 3-monochlorophenol 
• 217314-33-5 1-(3-chloro-4-iodophenyl)-2,5-dimethyl-1H-pyrrole 
• 4920-79-0 2-chloro-4-nitroanisole 

Downstream Products

• 19021-13-7 7-chloro-2-(4-chloro-phenyl)-6-methoxy-quinoline-4-carboxylic acid 
• 855948-96-8 2-(3-chloro-4-methoxy-anilino)-5-methoxy-benzoic acid 
• 50355-34-5 3-hydroxy-[2]naphthoic acid-(3-chloro-4-methoxy-anilide) 
• 23745-24-6 Cyclopropanecarboxylic acid (3-chloro-4-methoxy-phenyl)-amide 
• 20945-74-8 4-ethanesulfonyl-2-chloro-1-methoxy-benzene 
• 49755-07-9 N,N'-Bis-(3-chloro-4-methoxy-phenyl)-formamidine 
• 57729-95-0 (3-Chloro-4-methoxy-phenyl)-(2,4-dinitro-6-trifluoromethyl-phenyl)-amine 
• 70339-04-7 4'-methoxy-3'-chloro-1-methylcyclopropanecarboxanilide 
• 23742-74-7 1-(3-Chloro-4-methoxy-phenyl)-3-(4-trifluoromethyl-phenyl)-urea 
• 162321-41-7 (3-Chloro-4-methoxy-phenyl)-[dihydro-thiopyran-(3Z)-ylidene]-amine 
• 153865-36-2 (3-Chloro-4-methoxy-phenyl)-[1-thiophen-2-yl-eth-(E)-ylidene]-amine 
• 73541-47-6 6-[(3-Chloro-4-methoxy-phenylamino)-methyl]-1H-pyrimidine-2,4-dione 
• 35331-82-9 (3-Chloro-4-methoxy-phenyl)-cyclohexylidene-amine 
• 153865-38-4 3-(3-Chloro-4-methoxy-phenylamino)-cyclohex-2-enone 

Relevant academic research and scientific papers

NaI/PPh3-Mediated Photochemical Reduction and Amination of Nitroarenes

A mild transition-metal- and photosensitizer-free photoredox system based on the combination of NaI and PPh3 was found to enable highly selective reduction of nitroarenes. This protocol tolerates a broad range of reducible functional groups such as halogen (Cl, Br, and even I), aldehyde, ketone, carboxyl, and cyano. Moreover, the photoredox catalysis with NaI and stoichiometric PPh3 provides also an alternative entry to Cadogan-type reductive amination when o-nitrobiarenes were used.

Nucleophilic aromatic substitution of unactivated fluoroarenes enabled by organic photoredox catalysis

Nucleophilic aromatic substitution (SNAr) is a classical reaction with well-known reactivity toward electron-poor fluoroarenes. However, electron-neutral and electron-rich fluoro(hetero)arenes are considerably underrepresented. Herein, we present a method for the nucleophilic defluorination of unactivated fluoroarenes enabled by cation radical-accelerated nucleophilic aromatic substitution. The use of organic photoredox catalysis renders this method operationally simple under mild conditions and is amenable to various nucleophile classes, including azoles, amines, and carboxylic acids. Select fluorinated heterocycles can be functionalized using this method. In addition, the late-stage functionalization of pharmaceuticals is also presented. Computational studies demonstrate that the site selectivity of the reaction is dictated by arene electronics.

Discovery and characterization of an acridine radical photoreductant

Photoinduced electron transfer (PET) is a phenomenon whereby the absorption of light by a chemical species provides an energetic driving force for an electron-transfer reaction1–4. This mechanism is relevant in many areas of chemistry, including the study of natural and artificial photosynthesis, photovoltaics and photosensitive materials. In recent years, research in the area of photoredox catalysis has enabled the use of PET for the catalytic generation of both neutral and charged organic free-radical species. These technologies have enabled previously inaccessible chemical transformations and have been widely used in both academic and industrial settings. Such reactions are often catalysed by visible-light-absorbing organic molecules or transition-metal complexes of ruthenium, iridium, chromium or copper5,6. Although various closed-shell organic molecules have been shown to behave as competent electron-transfer catalysts in photoredox reactions, there are only limited reports of PET reactions involving neutral organic radicals as excited-state donors or acceptors. This is unsurprising because the lifetimes of doublet excited states of neutral organic radicals are typically several orders of magnitude shorter than the singlet lifetimes of known transition-metal photoredox catalysts7–11. Here we document the discovery, characterization and reactivity of a neutral acridine radical with a maximum excited-state oxidation potential of ?3.36 volts versus a saturated calomel electrode, which is similarly reducing to elemental lithium, making this radical one of the most potent chemical reductants reported12. Spectroscopic, computational and chemical studies indicate that the formation of a twisted intramolecular charge-transfer species enables the population of higher-energy doublet excited states, leading to the observed potent photoreducing behaviour. We demonstrate that this catalytically generated PET catalyst facilitates several chemical reactions that typically require alkali metal reductants and can be used in other organic transformations that require dissolving metal reductants.

Direct synthesis of anilines and nitrosobenzenes from phenols

A one-pot synthesis of anilines and nitrosobenzenes from phenols has been developed using an ipso-oxidative aromatic substitution (iSOAr) process. The products are obtained in good yields under mild and metal-free conditions. The leaving group effect on reactions that proceed through mixed quionone monoketals has also been investigated and a predictive model has been established.

Site-selective arene C-H amination via photoredox catalysis

Over the past several decades, organometallic cross-coupling chemistry has developed into one of the most reliable approaches to assemble complex aromatic compounds from preoxidized starting materials. More recently, transition metal-catalyzed carbon-hydrogen activation has circumvented the need for preoxidized starting materials, but this approach is limited by a lack of practical amination protocols. Here, we present a blueprint for aromatic carbon-hydrogen functionalization via photoredox catalysis and describe the utility of this strategy for arene amination. An organic photoredox-based catalyst system, consisting of an acridinium photooxidant and a nitroxyl radical, promotes site-selective amination of a variety of simple and complex aromatics with heteroaromatic azoles of interest in pharmaceutical research. We also describe the atom-economical use of ammonia to form anilines, without the need for prefunctionalization of the aromatic component.

Pd/C-mediated depropargylation of propargyl ethers/amines in water

Propargyl ethers and amines are effectively depropargylated to the parent alcohols or amines via a C-O/C-N bond cleavage catalyzed by 10% Pd/C in water. This simple, facile, and inexpensive methodology could be utilized for the selective removal of propargyl groups from a variety of aryl ethers and amines.

A new class of heterogeneous platinum catalysts for the chemoselective hydrogenation of nitroarenes

A new series of nanostructured platinum catalysts able to catalyze the selective reduction of nitroarenes has been developed. The materials, made of organosilica physically doped with nanostructured platinum(0), are stable and efficient. Reactions in general proceed with high yield and often go to completion, while the catalysts can be reused in further reaction runs. This establishes a new class of relevant solid catalysts for synthetic organic chemistry named SiliaCat Platinum-Hydrogel.

4′-Alkoxyl substitution enhancing the anti-mitotic effect of 5-(3′,4′,5′-substituted)anilino-4-hydroxy-8-nitroquinazolines as a novel class of anti-microtubule agents

Mitosis inhibitors are powerful anticancer drugs. Based on a novel anti-microtubule agent of 5-(4′-methoxy)anilino-4-hydroxy-8-nitroquinazoline, a series of 5-(3′,4′,5′-substituted)anilino-4-hydroxy-8- nitroquinazolines were designed and synthesized to investigate the effect of the substitution on the inhibitory activity against mitotic progression of tumor cells. The large alkoxyl substitution on the 4′-position of 5-anilino ring is beneficial for the potency. The 5-(3′,4′,5′-trimethoxy)anilino-8-nitroquinazoline (1h) displays an overwhelming activity in arresting the cells at the G2/M phase, providing a promising new template for further development of potent microtubule-targeted anti-mitotic drugs.

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.

New 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.