5465-66-7

Basic information

• Product Name: 1-(4-bromo-2-nitrophenyl)piperidine
• Synonyms: 1-(4-bromo-2-nitrophenyl)piperidine
• CAS NO: 5465-66-7
• Molecular Formula: C₁₁H₁₃BrN₂O₂
• Molecular Weight: 285.13712
• Mol File: 5465-66-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 388.1°Cat760mmHg
• Flash Point: 188.5°C
• Appearance: /
• Density: 1.502g/cm³
• Vapor Pressure: 3.15E-06mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: 1-(4-bromo-2-nitrophenyl)piperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-bromo-2-nitrophenyl)piperidine(5465-66-7)
• EPA Substance Registry System: 1-(4-bromo-2-nitrophenyl)piperidine(5465-66-7)

Safety Data

• Hazardous Substances Data: 5465-66-7(Hazardous Substances Data)

Usage

Description

1-(4-bromo-2-nitrophenyl)piperidine, also known as 4-bromo-2-nitrophenylpiperidine, is a chemical compound with the molecular formula C11H13BrN2O2. It is a piperidine derivative that contains a bromine atom and a nitro group attached to a phenyl ring. 1-(4-bromo-2-nitrophenyl)piperidine is characterized by its potential for versatile applications in the chemical and pharmaceutical industries due to its unique structural features.

Uses

Used in Research and Development:
1-(4-bromo-2-nitrophenyl)piperidine is used as a research compound for the development of new pharmaceuticals. Its unique structure, which includes a bromine atom and a nitro group, makes it a valuable building block for the synthesis of biologically active compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-(4-bromo-2-nitrophenyl)piperidine is used as an intermediate in the synthesis of various organic compounds. Its presence as a key structural component can contribute to the development of new drugs with specific therapeutic properties.
Used as a Ligand in Metal Ion Complexes:
1-(4-bromo-2-nitrophenyl)piperidine also serves as a ligand for the formation of metal ion complexes. This application is significant in various chemical processes and can lead to the creation of novel materials with specialized properties.
Overall, 1-(4-bromo-2-nitrophenyl)piperidine is a versatile compound with a wide range of applications in both the chemical and pharmaceutical sectors, making it an important asset for researchers and developers in these fields.

InChI:InChI=1/C11H13BrN2O2/c12-9-4-5-10(11(8-9)14(15)16)13-6-2-1-3-7-13/h4-5,8H,1-3,6-7H2

Upstream product

• 110-89-4 piperidine 
• 3460-18-2 1,4-dibromo-2-nitrobenzene 
• 55321-64-7 (4-bromo-2-nitro-phenyl)-p-tolyl ether 
• 33696-00-3 4-bromo-1-methoxy-2-nitrobenzene 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 364-73-8 4-Bromo-1-fluoro-2-nitrobenzene 
• 16588-24-2 4-bromo-1-chloro-2-nitrobenzene 

Downstream Products

• 885704-46-1 4-(3-nitro-4-(piperidin-1-yl)phenyl)morpholine 
• 1016877-65-8 5-bromo-2-(piperidin-1-yl)aniline 

Relevant articles and documents

Optimisation of 2-(N-phenyl carboxamide) triazolopyrimidine antimalarials with moderate to slow acting erythrocytic stage activity

Malaria is a devastating parasitic disease caused by parasites from the genus Plasmodium. Therapeutic resistance has been reported against all clinically available antimalarials, threatening our ability to control the disease and therefore there is an ongoing need for the development of novel antimalarials. Towards this goal, we identified the 2-(N-phenyl carboxamide) triazolopyrimidine class from a high throughput screen of the Janssen Jumpstarter library against the asexual stages of the P. falciparum parasite. Here we describe the structure activity relationship of the identified class and the optimisation of asexual stage activity while maintaining selectivity against the human HepG2 cell line. The most potent analogues from this study were shown to exhibit equipotent activity against P. falciparum multidrug resistant strains and P. knowlesi asexual parasites. Asexual stage phenotyping studies determined the triazolopyrimidine class arrests parasites at the trophozoite stage, but it is likely these parasites are still metabolically active until the second asexual cycle, and thus have a moderate to slow onset of action. Non-NADPH dependent degradation of the central carboxamide and low aqueous solubility was observed in in vitro ADME profiling. A significant challenge remains to correct these liabilities for further advancement of the 2-(N-phenyl carboxamide) triazolopyrimidine scaffold as a potential moderate to slow acting partner in a curative or prophylactic antimalarial treatment.

COMPOUNDS

The present invention relates to a compound of formula (Ia), or a pharmaceutically acceptable salt or hydrate thereof, wherein: the group X-Y is -NHSO2- or -SO2NH-; R1 is H or alkyl; R2 is selected from COOH and a tetrazolyl group; R3 is selected from H, Cl and alkyl; R4 is selected from H, Cl and F; R5 is selected from H, alkyl, alkynyl, alkenyl, haloalkyl, SO2-alkyl, Cl, alkoxy, OH, CN, hydroxyalkyl, alkylthio, heteroaryl, cycloalkyl, heterocycloalkyl and haloalkoxy; R6 is H; R7 is selected from H, CN, haloalkyl, Cl, F, SO2-alkyl, SO2NR13R14, optionally substituted heteroaryl and alkyl; R8 is selected from H, alkyl, haloalkyl and halo; R9 is H, C1-C3-alkyl, or halo; R10 and R11, together with the nitrogen to which they are attached, form an azepanyl group, wherein (a) said azepanyl group is substituted by one or more substituents, or (b) one or two carbons in said azepanyl group are replaced by a group selected from O, NH, S and CO, and said azepanyl group is optionally further substituted; or R10 and R11, together with the nitrogen to which they are attached, form an azetidinyl, pyrrolidinyl or piperidinyl group wherein (a) said azetidinyl, pyrrolidinyl or piperidinyl group is substituted by one or more substituents, or (b) one or two carbons in said azetidinyl, pyrrolidinyl or piperidinyl group are replaced by a group selected from NH, S and CO; or R10 and R11, together with the nitrogen to which they are attached, form an 8, 9 or 10-membered bicyclic heterocycloalkyl group, wherein one or two carbons in the bicyclic heterocycloalkyl ring are optionally replaced by a group selected from O, NH, S and CO, and said bicyclic heterocycloalkyl group is optionally substituted; or R10 and R11, together with the nitrogen to which they are attached, form a 6 to 12-membered bicyclic group containing a spirocyclic carbon atom, wherein one or two carbons in the bicyclic group are optionally replaced by a group selected from O, NH, S and CO, and said bicyclic group is optionally substituted, or said bicyclic group is optionally fused to a 5 or 6-membered aryl or heteroaryl group; R13 and R14 are each independently H or alkyl. Further aspects of the invention relate to such compounds for use in the field of immune-oncology and related applications.

Synthesis and bioevaluation of 1-phenyl-pyrazole-4-carboxylic acid derivatives as potent xanthine oxidoreductase inhibitors

A diverse library of 1-phenyl-pyrazole-4-carboxylic acid derivatives were synthesized and evaluated for their inhibitory potency against xanthine oxidoreductase (XOR) in vitro and vivo, and the structure-activity relationship (SAR) analyses were also pres