443882-99-3

Basic information

• Product Name: 3-Chloro-4-(3-fluorobenzyloxy)nitrobenzene
• Synonyms: 3-Chloro-4-(3-fluorobenzyloxy)nitrobenzene;2-Chloro-1-(3-fluoro-benzyloxy)-4-nitrobenzene;1-(3-fluorobenzyloxy)-2-chloro-4-nitrobenzene;Benzene,2-chloro-1-[(3-fluorophenyl)Methoxy]-4-nitro-;1-Fluoro-3-[(4-nitro-2-chlorophenoxy)Methyl]benzene;4-(3-Fluorobenzyloxy)-3-chloronitrobenzene;2-Chloro-1-(3-fluoro-benzyloxy)-4-nitro-;Lapatinib genotoxic impurity 2
• CAS NO: 443882-99-3
• Molecular Formula: C₁₃H₉ClFNO₃
• Molecular Weight: 281.67
• Mol File: 443882-99-3.mol

Chemical Properties

• Melting Point: 99.0 to 103.0 °C
• Boiling Point: 400.5 °C at 760 mmHg
• Flash Point: 196 °C
• Appearance: /
• Density: 1.393 g/cm³
• Vapor Pressure: 2.92E-06mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 3-Chloro-4-(3-fluorobenzyloxy)nitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloro-4-(3-fluorobenzyloxy)nitrobenzene(443882-99-3)
• EPA Substance Registry System: 3-Chloro-4-(3-fluorobenzyloxy)nitrobenzene(443882-99-3)

Safety Data

• Hazardous Substances Data: 443882-99-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Chloro-4-(3-fluorobenzyloxy)nitrobenzene is used as a key intermediate in the synthesis of novel indole-2-carboxamide derivatives, which are known for their anti-inflammatory properties. These derivatives are particularly useful in the treatment of sepsis, a life-threatening condition characterized by the body's extreme response to infection.
Additionally, 3-Chloro-4-(3-fluorobenzyloxy)nitrobenzene plays a significant role in the production of Niraparib (N481400), a novel oral poly(ADP-ribose)polymerase (PARP) inhibitor. Niraparib has demonstrated efficacy in treating BRCA-1 and -2 mutant tumors, which are associated with an increased risk of developing breast and ovarian cancers. By inhibiting PARP enzymes, Niraparib helps to prevent the repair of damaged DNA in cancer cells, ultimately leading to their death.

InChI:InChI=1/C13H9ClFNO3/c14-12-7-11(16(17)18)4-5-13(12)19-8-9-2-1-3-10(15)6-9/h1-7H,8H2

Upstream product

• 619-08-9 2-chloro-4-nitrophenol 
• 456-41-7 1-(Bromomethyl)-3-fluorobenzene 
• 350-30-1 3-chloro-4-fluoronitrobenzene 
• 456-47-3 3-fluoro-benzenemethanol 
• 99-54-7 3,4-dichloronitrobenzene 
• 456-42-8 m-fluorobenzyl chloride 

Downstream Products

• 848133-14-2 4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-6-amino-7-ethoxyquinoline-3-carbonitrile 
• 231278-20-9 N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-iodoquinazolin-4-amine 
• 1260401-93-1 N-(3-chloro-4(3-fluorobenzyloxy)phenyl)-6-(3-(4-methyl-1,4-azaphosphine1-yl)propan-1-yn)quinazolin-4-amine 
• 1260401-94-2 N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-(3-(4-methyl-1,4-azaphosphino-1-yl)propyl)quinazolin-4-amine 
• 552294-86-7 6-bromo-N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)thieno[2,3-d]pyrimidin-4-amine 

Relevant articles and documents

Discovery of novel and potent safinamide-based derivatives as highly selective hMAO-B inhibitors for treatment of Parkinson's disease (PD): Design, synthesis, in vitro, in vivo and in silico biological studies

Up to date, the current clinical practice employs only symptomatic treatments for management of Parkinson's disease (PD) but unable to stop disease progression. The discovery of new chemical entities endowed with potent and selective human monoamine oxidase B (hMAO-B) inhibitory activity is a clinically relevant subject. Herein, a structural optimization strategy for safinamide (a well-known second generation hMAO-B inhibitor) afforded a series of thirty-six safinamide-derived new analogs (4aa–bj). Most compounds showed promising inhibitory activities against hMAO-B (>70% inhibition at a single dose concentration of 10 μM), with no apparent effect on hMAO-A at 100 μM. Moreover, while six compounds (4ak, 4as, 4az, 4be, 4bg, and 4bi) exhibited potent double-digit nanomolar activities over hMAO-B with IC50 values of 29.5, 42.2, 22.3, 18.8, 42.2, and 33.9 nM, respectively, three derivatives (4aq, 4at, and 4bf), possessing the same carboxamide moiety (2-pyrazinyl), showed the most potent single-digit nanomolar activities (IC50 = 9.7, 5.1, and 3.9 nM, respectively). Compound 4bf revealed an excellent selectivity index (SI > 25641) with a 29-fold increase compared to safinamide (SI > 892). A structure activity relationship along with molecular docking simulations provided insights into enzyme ? inhibitor interactions and a rational for the observed activity. In an in vivo MPTP-induced mouse model of PD, oral administration of compound 4bf significantly protected nigrostriatal dopaminergic neurons as revealed by tyrosine hydroxylase staining and prevented MPTP-induced Parkinsonism as revealed by motor behavioral assays. Accordingly, we present compound 4bf as a novel, highly potent, and selective hMAO-B inhibitor with an effective therapeutic profile for relieving PD.

HER2 Kinase-Targeted Breast Cancer Therapy: Design, Synthesis, and in Vitro and in Vivo Evaluation of Novel Lapatinib Congeners as Selective and Potent HER2 Inhibitors with Favorable Metabolic Stability

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Mutated or amplified Her2 serves as a driver of non-small cell lung cancer or mediates resistance toward the inhibition of its family member epidermal growth factor receptor with small-molecule inhibitors. To date, small-molecule inhibitors targeting Her2 which can be used in clinical routine are lacking, and therefore, the development of novel inhibitors was undertaken. In this study, the well-established pyrrolopyrimidine scaffold was modified with structural motifs identified from a screening campaign with more than 1600 compounds, which were applied against wild-type Her2 and its mutant variant Her2-A775_G776insYVMA. The resulting inhibitors were designed to covalently target a reactive cysteine in the binding site of Her2 and were further optimized by means of structure-based drug design utilizing a set of obtained complex crystal structures. In addition, the analysis of binding kinetics and absorption, distribution, metabolism, and excretion parameters as well as mass spectrometry experiments and western blot analysis substantiated our approach.

A process for preparing the lapatinib method and intermediate (by machine translation)

A through novel intermediate to prepare lapatinib or its pharmaceutically acceptable salt of the method, the method using 5 - bromo furfural and and 2 - nitrobenzene formic acid as the starting material through the Suzuki coupling reaction. This kind of synthetic pulls the handkerchief to raise nepal method can reach 32.2% overall yield. (by machine translation)

1,2-DITHIOLANE AND DITHIOL COMPOUNDS USEFUL IN TREATING MUTANT EGFR-MEDIATED DISEASES AND CONDITIONS

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