190777-77-6

Basic information

• Product Name: 5-BROMOISOQUINOLIN-1(2H)-ONE
• Synonyms: 5-BROMOISOQUINOLIN-1(2H)-ONE;5-Bromo-1(2H)-isoquinolinone;5-bromoisoquinolin-1-ol;5-Bromo-1,2-dihydro-1-oxoisoquinoline;5-Bromo-2H-isoquinolin-1-one;5-Bromoisoquinolin-1(2H);5-bromo-1,2-dihydroisoquinolin-1-one
• CAS NO: 190777-77-6
• Molecular Formula: C₉H₆BrNO
• Molecular Weight: 224.05
• Mol File: 190777-77-6.mol

Chemical Properties

• Boiling Point: 443.15 °C at 760 mmHg
• Flash Point: 221.809 °C
• Appearance: /
• Density: 1.620
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.63
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.19±0.20(Predicted)
• CAS DataBase Reference: 5-BROMOISOQUINOLIN-1(2H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMOISOQUINOLIN-1(2H)-ONE(190777-77-6)
• EPA Substance Registry System: 5-BROMOISOQUINOLIN-1(2H)-ONE(190777-77-6)

Safety Data

• Hazardous Substances Data: 190777-77-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
5-bromoisoquinolin-1(2H)-one is used as an intermediate for the synthesis of potential therapeutic agents, contributing to the development of new medications with diverse therapeutic properties.
Used in Agrochemical Production:
In the agrochemical industry, 5-bromoisoquinolin-1(2H)-one serves as a starting material for the production of herbicides and pesticides, helping to create effective solutions for weed and pest control in agriculture.
Used in Organic Synthesis:
5-bromoisoquinolin-1(2H)-one is utilized as a reagent in organic synthesis, particularly for the preparation of various heterocyclic compounds, which are essential building blocks in the creation of complex organic molecules with specific applications in different fields.

InChI:InChI=1/C9H6BrNO/c10-8-3-1-2-7-6(8)4-5-11-9(7)12/h1-5H,(H,11,12)

Upstream product

• 1711-09-7 3-bromobenzoyl chloride 
• 585-76-2 m-bromobenzoic acid 
• 108-05-4 vinyl acetate 
• 1427180-45-7 (3-bromophenyl)formamido 2,2-dimethylpropanoate 
• 1109230-25-2 5-bromo-1,2,3,4-tetrahydroisoquinolin-1-one 
• 15115-60-3 4-bromo-2,3-dihydroinden-1-one 
• 223671-17-8 5-bromoisoquinolin-2-ium-2-olate 
• 34784-04-8 5-bromoisoquinoline 
• 77747-69-4 5-nitro-1H-isochromen-1-one 
• 70758-25-7 5-aminoisocoumarin 
• 245677-36-5 5-bromoisocoumarin 
• 1026708-78-0 (E)-3-(2-Bromo-phenyl)-acryloyl azide 

Downstream Products

• 1367905-79-0 5-bromo-2-methyl-2H-isoquinolin-1-one 
• 1207448-46-1 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-dihydroisoquinolin-1-one 

Relevant articles and documents

Efficient visible light mediated synthesis of quinolin-2(1H)-ones from quinolineN-oxides

Quinolin-2(1H)-ones are one of the important classes of compounds due to their prevalence in natural products and in pharmacologically useful compounds. Here we present an unconventional and hitherto unknown photocatalytic approach to their synthesis from easily available quinoline-N-oxides. This reagent free highly atom economical photocatalytic method, with low catalyst loading, high yield and no undesirable by-product, provides an efficient greener alternative to all conventional synthesis reported to date. The robustness of the methodology has been successfully demonstrated with easy scaling up to the gram scale.

MALT1 MODULATORS AND USES THEREOF

Provided herein are compounds, compositions, and methods useful for modulating MALT1 and for treating related diseases, disorders, and conditions.

New Series of Potent Allosteric Inhibitors of Deoxyhypusine Synthase

Deoxyhypusine synthase (DHPS) is the primary enzyme responsible for the hypusine modification and, thereby, activation of the eukaryotic translation initiation factor 5A (eIF5A), which is key in regulating the protein translation processes associated with tumor proliferation. Although DHPS inhibitors could be a promising therapeutic option for treating cancer, only a few studies reported druglike compounds with this inhibition property. Thus, in this work, we designed and synthesized a new chemical series possessing fused ring scaffolds designed from high-throughput screening hit compounds, discovering a 5,6-dihydrothieno[2,3-c]pyridine derivative (26d) with potent inhibitory activity; furthermore, the X-ray crystallographic analysis of the DHPS complex with 26d demonstrated a distinct allosteric binding mode compared to a previously reported inhibitor. These findings could be significantly useful in the functional analysis of conformational changes in DHPS as well as the structure-based design of allosteric inhibitors.

Light-induced [2 + 2] cycloadditions for the construction of cyclobutane-fused pyridinyl sulfonyl fluorides

Cyclobutanes are an important class of motifs present in a wide range of natural products and other biologically significant molecules. A photocatalytic [2 + 2] cycloaddition between pyridones or isoquinolones and ethenesulfonyl fluoride was achieved, providing a portal to a class of unique cyclobutane-fused pyridinyl sulfonyl fluorides with quaternary rigid rings (30 examples). Further applications of these novel sulfonyl fluoride molecules in SuFEx click chemistry were also accomplished, providing the corresponding sulfonates and sulphonamides with reasonable yields.

A nitrogen oxide C2 - bit hydroxylated method (by machine translation)

The present invention relates to nitrogen oxide C2 - bit hydroxylated method, in particular under reflux conditions in dichloroethane, three pyrrole alkyl bromide (PyBrop) [...] phosphate, sodium acetate, water and nitrogen oxides produced by the reaction of hydroxyl-substituted product. The process has simple operation, mild condition, high reaction selectivity, substrate wide applicability, high yield and the like. The application for the first time using this method to synthesize a series of 2 - hydroxyquinoline, 2 - hydroxy pyridine and 1 - hydroxy isoquinoline compound, in the establishment of the compounds of the library synthesis application have broad prospects. (by machine translation)

CARBAZOLE COMPOUNDS AND METHODS OF USING SAME

The present invention provides carbazole compounds of the formula (I), which can be used for treating microbial, protozoan, viral infections and cancer. ?

CARBAZOLE COMPOUNDS AND METHODS OF USING SAME

The invention relates to carbazole compounds of formula (I) that can be used for treating microbial infections, in particular, fungal infections, and selectively kill cancer cells.

FUSED INDOLE COMPOUNDS AND METHODS OF USING SAME

The invention relates to fused indole compounds of formula (I) that can be used for treating microbial infections, in particular, fungal infections, and selectively kill cancer cells.

Expeditious Synthesis of the Topoisomerase i Inhibitors Isoindolo[2,1- b ]isoquinolin-7(5 H)-one and the Alkaloid Rosettacin Based on Aryl Radical Cyclization of Enamide Generated by Using N -Acylaiminium Chemistry

A short and effective approach to the synthesis of the topoisomerase I inhibitor isoindolo[2,1-b]isoquinolin-7(5H)-one and the alkaloid rosettacin belonging to the aromathecin family is presented. The key step of this sequence, which resulted in the formation of a five-membered ring, was the aryl radical cyclization of enamides generated using N-acyliminium chemistry.

Enantioselective template-directed [2+2] photocycloadditions of isoquinolones: Scope, mechanism and synthetic applications

A strategy for the enantioselective [2+2] photocycloaddition of isoquinolones with alkenes is presented, in which the formation of a supramolecular complex between a chiral template and the substrate ensures high enantioface differentiation by shielding one face of the substrate. Fifteen different electron-deficient alkenes and ten different substituted isoquinolones undergo efficient photocycloaddition, yielding the cyclobutane products in excellent yields and with outstanding regio-, diastereo- and enantioselectivities (up to 990 ee). The mechanism of the reaction is investigated by means of triplet sensitization/quenching and radical clock experiments, the results of which are consistent with the involvement of a triplet excited state and a 1,4-biradical intermediate. The variety of functionalized cyclobutanes obtained using this approach can be further increased by straightforward synthetic transformations of the photoadducts, allowing rapid access to libraries of compounds for various applications.