1810-71-5

Basic information

• Product Name: 2-CHLORO-6-BROMOQUINOLINE
• Synonyms: 6-BROMO-2-CHLORO-QUINOLINE;2-Chloro-6-bromoquinoline;4,4'',4''-TRIIODOTRIPHENYLAMINE;Quinoline, 6-bromo-2-chloro-;6-broMo-2-chloro-;6-Bromo-2-chloro-1-azanaphthalene
• CAS NO: 1810-71-5
• Molecular Formula: C₉H₅BrClN
• Molecular Weight: 242.5
• EINECS: 1312995-182-4
• Product Categories: Aromatics Compounds;CHIRAL CHEMICALS;Aromatics;Heterocycles
• Mol File: 1810-71-5.mol

Chemical Properties

• Melting Point: 148-150℃
• Boiling Point: 325.7°Cat760mmHg
• Flash Point: 150.8°C
• Appearance: /
• Density: 1.673g/cm³
• Vapor Pressure: 0.000429mmHg at 25°C
• Refractive Index: 1.68
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Soluble in Chloroform and Methanol
• PKA: -0.48±0.43(Predicted)
• CAS DataBase Reference: 2-CHLORO-6-BROMOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-6-BROMOQUINOLINE(1810-71-5)
• EPA Substance Registry System: 2-CHLORO-6-BROMOQUINOLINE(1810-71-5)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN2811
• Hazardous Substances Data: 1810-71-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H5BrClN/c10-7-2-3-8-6(5-7)1-4-9(11)12-8/h1-5H

Upstream product

• 5332-25-2 6-bromoquinoline 
• 1810-66-8 6-bromoquinoline-2-ol 
• 6563-11-7 6-bromoquinoline-N-oxide 
• 54934-81-5 N-(4-bromophenyl)prop-2-enamide 
• 106-40-1 4-bromo-aniline 
• 553-03-7 3,4-dihydro-2(1H)-quinolone 
• 327058-51-5 N-(4-bromophenyl)-(E)-3-ethoxyacrylamide 
• 71205-21-5 methyl (E)-3-(2-amino-5-bromophenyl)prop-2-enoate 
• 66416-72-6 4-bromo-2-iodoaniline 
• 3279-90-1 6-bromo-3,4-dihydro-1H-quinolin-2-one 
• 1810-66-8 6-bromo-2-quinolone 

Downstream Products

• 205055-71-6 2-chloro-6-chlorosulfonylquinoline 
• 99455-05-7 2-methoxy-6-bromoquinoline 
• 1085755-63-0 methyl 1-(2-chloroquinolin-6-yl)piperidine-4-carboxylate 
• 1085755-96-9 methyl 1-(2-methoxyquinolin-6-yl)piperidine-4-carboxylate 
• 1085755-59-4 2-chloro-6-(4-phenylpiperidin-1-yl)quinoline 
• 1085755-93-6 6-bromo-2-tert-butoxyquinoline 
• 1085755-69-6 2-chloro-6-(4-phenylpiperazin-1-yl)quinoline 
• 1085755-77-6 6-bromo-2-(4-phenylpiperazin-1-yl)quinoline 
• 1085755-61-8 2-chloro-6-(4-benzylpiperidin-1-yl)quinoline 
• 1085756-00-8 C₂₁H₂₁BrN₂ 
• 1085755-85-6 2-tert-butoxy-6-(4-benzylpiperidin-1-yl)quinoline 
• 1085755-79-8 2-(4-benzylpiperazin-1-yl)-6-bromoquinoline 
• 1085755-71-0 6-(4-benzylpiperazin-1-yl)-2-chloroquinoline 
• 1085755-89-0 2-tert-butoxy-6-(4-benzylpiperazn-1-yl)quinoline 

Relevant articles and documents

Aminoquinoline-rhodium(II) conjugates as src-family SH3 ligands

High-affinity, selective ligands are sought for a variety of biomolecules but are particularly difficult to generate in the protein-protein interaction space. Rhodium(II) conjugates provide a structure-based approach to improved affinity and specificity f

IMIDAZOLIDINONE DERIVATIVES AS INHIBITORS OF PERK

The invention is directed to substituted imidazolidinone derivatives. Specifically, the invention is directed to compounds according to Formula I (I) wherein R1, R2, R3, R4, R5, R6, R7, X, Y1, Y2 and Z are defined herein. The compounds of the invention are inhibitors of PERK and can be useful in the treatment of cancer, pre-cancerous syndromes, as Alzheimer's disease, neuropathic pain, spinal cord injury, traumatic brain injury, ischemic stroke, stroke, Parkinson disease, diabetes, metabolic syndrome, metabolic disorders, Huntington's disease, Creutzfeldt-Jakob Disease, fatal familial insomnia, Gerstmann-Str?ussler-Scheinker syndrome, and related prion diseases, amyotrophic lateral sclerosis, progressive supranuclear palsy, myocardial infarction, cardiovascular disease, inflammation, organ fibrosis, chronic and acute diseases of the liver, fatty liver disease, liver steatosis, liver fibrosis, chronic and acute diseases of the lung, lung fibrosis, chronic and acute diseases of the kidney, kidney fibrosis, chronic traumatic encephalopathy (CTE), neurodegeneration, dementias, frontotemporal dementias, tauopathies, Pick's disease, Neimann-Pick's disease, amyloidosis, cognitive impairment, atherosclerosis, ocular diseases, arrhythmias, in organ transplantation and in the transportation of organs for transplantation. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting PERK activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

Regioselective Chlorination of Quinoline N-Oxides and Isoquinoline N-Oxides Using PPh3/Cl3CCN

A novel method for the regioselective C2-chlorination of heterocyclic N-oxides has been developed. PPh3/Cl3CCN were used as chlorinating reagents and the desired N-heterocyclic chlorides were obtained smoothly in satisfactory yields. The reactions proceeded in a highly efficient and selective manner across a broad range of substrates demonstrating excellent functional group tolerance. In addition, this chlorination reaction can be used for the modification of N-heterocyclic scaffolds of appealing ligands and pharmaceuticals.

Enantioselective Intermolecular [2 + 2] Photocycloaddition Reactions of 2(1H)-Quinolones Induced by Visible Light Irradiation

In the presence of a chiral thioxanthone catalyst (10 mol %) the title compounds underwent a clean intermolecular [2 + 2] photocycloaddition with electron-deficient olefins at λ = 419 nm. The reactions not only proceeded with excellent regio- and diastereoselectivity but also delivered the respective cyclobutane products with significant enantiomeric excess (up to 95% ee). Key to the success of the reactions is a two-point hydrogen bonding between quinolone and catalyst enabling efficient energy transfer and high enantioface differentiation. Preliminary work indicated that solar irradiation can be used for this process and that the substrate scope can be further expanded to isoquinolones.

INHIBITORS OF RENAL OUTER MEDULLARY POTASSIUM CHANNEL

Novel spirocyclic compounds of formula I: and pharmaceutically acceptable salts thereof are disclosed as inhibitors of the ROMK (Kir1.1) channel. The compounds may be used as diuretic and/or natriuretic agents and for the therapy and prophylaxis of medical conditions including cardiovascular diseases such as hypertension, heart failure and chronic kidney disease and conditions associated with excessive salt and water retention. Pharmaceutical compositions and methods of treatment are also included.

INHIBITORS OF THE RENAL OUTER MEDULLARY POTASSIUM CHANNEL

Novel spirocyclic compounds of formula I: and pharmaceutically acceptable salts thereof are disclosed as inhibitors of the ROMK (Kir1.1) channel. The compounds may be used as diuretic and/or natriuretic agents and for the therapy and prophylaxis of medical conditions including cardiovascular diseases such as hypertension, heart failure and chronic kidney disease and conditions associated with excessive salt and water retention. Pharmaceutical compositions and methods of treatment are also included.

A practical and mild chlorination of fused heterocyclic N-oxides

Fused azine N-oxides were selectively chlorinated at C2 in moderate to excellent yields, employing Vilsmeier reagent as both the activating agent and the nucleophilic chloride source. Remarkable features of the method include simple operation, mild reaction conditions, a wide substrate scope, and the use of only stoichiometric amount of POCl3. The potential extension of this method to a one-pot oxidation/chlorination sequence that obviates the need for isolation of the N-oxide intermediates is also validated.

Synthesis and biological evaluation of 2-substituted quinoline 6-carboxamides as potential mGluR1 antagonists for the treatment of neuropathic pain

A series of 2-amino and 2-methoxy quinoline-6-carboxamide derivatives have been synthesized and their metabotropic glutamate receptor type 1 (mGluR1) antagonistic activities were evaluated in a functional cell-based assay. The compound 13c showed the highest potency with IC50 value of 2.16μM against mGluR1. Finally, in vivo evaluation of 13c in the rat spinal nerve ligation (SNL) model exhibited weak analgesic effects with regard to both mechanical allodynia and cold allodynia.

From fragment screening to in vivo efficacy: Optimization of a series of 2-aminoquinolines as potent inhibitors of beta-site amyloid precursor protein cleaving enzyme 1 (bace1)

Using fragment-based screening of a focused fragment library, 2-aminoquinoline 1 was identified as an initial hit for BACE1. Further SAR development was supported by X-ray structures of BACE1 cocrystallized with various ligands and molecular modeling studies to expedite the discovery of potent compounds. These strategies enabled us to integrate the C-3 side chain on 2-aminoquinoline 1 extending deep into the P2′ binding pocket of BACE1 and enhancing the ligand's potency. We were able to improve the BACE1 potency to subnanomolar range, over 106-fold more potent than the initial hit (900 μM). Further elaboration of the physical properties of the lead compounds to those more consistent with good blood-brain barrier permeability led to inhibitors with greatly improved cellular activity and permeability. Compound 59 showed an IC50 value of 11 nM on BACE1 and cellular activity of 80 nM. This compound was advanced into rat pharmacokinetic and pharmacodynamic studies and demonstrated significant reduction of Aβ levels in cerebrospinal fluid (CSF).

PHOSPHATIDYLINOSITOL 3 KINASE INHIBITORS

Provided are compounds according to Formula (I), or stereoisomer, prodrug, polymorph, or pharmaceutically acceptable salt forms thereof, wherein X, Y, R1, R6 , R7, and R8 are as defined, which compounds are effective inhibitors of PI3-kinase and/or other medically and clinically relevant kinases. Also provided are pharmaceutical compositions and methods of using the compounds and compositions as PB -kinase and kinase inhibitors. More particularly, the compounds of the invention provide treatments and therapeutics for human diseases regulated by, or associated with, the activity of, PI3-kinases and/or protein kinases, or mutant or variant forms thereof.