347840-11-3

Usage

Uses

Used in Pharmaceutical Synthesis:
3-CHLOROANILINE-2,4,6-D3 is used as a key intermediate in the synthesis of pyrimidoazepine analogs. These analogs act as serotonin 5-HT2A and 5-HT2C receptor ligands, which are crucial for the treatment of obesity. 3-CHLOROANILINE-2,4,6-D3's unique properties allow for the development of targeted therapies that can help address weight management issues.
Used in COX-2 Inhibitor Synthesis:
In addition to its role in obesity treatment, 3-CHLOROANILINE-2,4,6-D3 is also utilized in the synthesis of novel COX-2 inhibitors. COX-2 inhibitors are important in the management of pain and inflammation, making 3-CHLOROANILINE-2,4,6-D3 a valuable asset in the development of new medications for these conditions.
Overall, 3-CHLOROANILINE-2,4,6-D3 is a versatile compound with applications in various areas of pharmaceutical research and development, particularly in the synthesis of serotonin receptor ligands for obesity treatment and COX-2 inhibitors for pain and inflammation management.

Upstream product

• 4165-60-0 nitrobenzene-d5 
• 108-42-9 3-chloro-aniline 

Downstream Products

• 1027104-26-2 C₁₃⁽²⁾H₄H₈NClO₄ 

Relevant academic research and scientific papers

DEUTERATED CHLOROKYNURENINES FOR THE TREATMENT OF NEUROPSYCHIATRIC DISORDERS

Described are deuterated chlorokynurenines and compositions, and their application as pharmaceuticals for the treatment of disease. Methods of modulating N-methyl-D-aspartate (NMDA) receptor activity, methods of treating disorders, including neuropsychiatric disorders such as depression, epilepsy, schizophrenia, and Huntington's Disease, and use of said deuterated chlorokynurenines are also described.

Aromatic Hydroxylation at a Non-Heme Iron Center: Observed Intermediates and Insights into the Nature of the Active Species

Mechanism of substrate oxidations with hydrogen peroxide in the presence of a highly reactive, biomimetic, iron aminopyridine complex, [Fe II(bpmen)(CH3CN)2][ClO4] 2 (1; bpmen=N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2- diamine), is elucidated. Complex 1 has been shown to be an excellent catalyst for epoxidation and functional-group-directed aromatic hydroxylation using H2O2, although its mechanism of action remains largely unknown.1, 2 Efficient intermolecular hydroxylation of unfunctionalized benzene and substituted benzenes with H2O2 in the presence of 1 is found in the present work. Detailed mechanistic studies of the formation of iron(III)-phenolate products are reported. We have identified, generated in high yield, and experimentally characterized the key FeIII(OOH) intermediate (Imax=560 nm, rhombic EPR signal with g=2.21, 2.14, 1.96) formed by 1 and H2O2. Stopped-flow kinetic studies showed that FeIII(OOH) does not directly hydroxylate the aromatic rings, but undergoes rate-limiting self-decomposition producing transient reactive oxidant. The formation of the reactive species is facilitated by acid-assisted cleavage of the O-O bond in the iron-hydroperoxide intermediate. Acid-assisted benzene hydroxylation with 1 and a mechanistic probe, 2-Methyl-1-phenyl-2-propyl hydroperoxide (MPPH), correlates with O-O bond heterolysis. Independently generated FeIV=O species, which may originate from O-O bond homolysis in FeIII(OOH), proved to be inactive toward aromatic substrates. The reactive oxidant derived from 1 exchanges its oxygen atom with water and electrophilically attacks the aromatic ring (giving rise to an inverse H/D kinetic isotope effect of 0.8). These results have revealed a detailed experimental mechanistic picture of the oxidation reactions catalyzed by 1, based on direct characterization of the intermediates and products, and kinetic analysis of the individual reaction steps. Our detailed understanding of the mechanism of this reaction revealed both similarities and differences between synthetic and enzymatic aromatic hydroxylation reactions.