34784-05-9

Basic information

• Product Name: 6-Bromoisoquinoline
• Synonyms: 6-BROMOISOQUINOLINE;NSC 229320;Isoquinoline, 6-bromo-;6-Bromoisoquinoline ,97%;6-Bromoisoquinoline ,99%;6-Bromo-2-azanaphthalene;6-BroMoisoquinoline Monohydrate
• CAS NO: 34784-05-9
• Molecular Formula: C₉H₆BrN
• Molecular Weight: 208.05
• EINECS: -0
• Product Categories: Quinoline series;Heterocyclic Series;Halides;Quinolines, Isoquinolines & Quinoxalines;Isoquinoline Derivertives;Building Blocks;Isoquinoline;Quinolines;Quinolines, Isoquinolines & Quinoxalines
• Mol File: 34784-05-9.mol

Chemical Properties

• Melting Point: 44.0 to 48.0 °C
• Boiling Point: 312.3 °C at 760 mmHg
• Flash Point: >110℃
• Appearance: White/Crystalline Powder
• Density: 1.564 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.674
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 4.83±0.10(Predicted)
• CAS DataBase Reference: 6-Bromoisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromoisoquinoline(34784-05-9)
• EPA Substance Registry System: 6-Bromoisoquinoline(34784-05-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-36-20/21/22
• Safety Statements: 26-36/37/39-24/25
• WGK Germany: 1
• Hazardous Substances Data: 34784-05-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Bromoisoquinoline is used as a building block in organic synthesis for the development of pharmaceuticals, leveraging its bromine-substituted structure to create a variety of biologically active compounds with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 6-Bromoisoquinoline is utilized as a key intermediate in the synthesis of agrochemicals, contributing to the development of effective pesticides and other agricultural chemicals.
Used in Medicinal Chemistry Research:
6-Bromoisoquinoline is employed as a subject of investigation in medicinal chemistry due to its demonstrated anti-cancer, anti-inflammatory, and anti-microbial activities, making it a promising candidate for the discovery of new drugs and therapeutic agents.
Used in Drug Development and Discovery:
As a versatile starting material, 6-Bromoisoquinoline is used for the synthesis of diverse molecular scaffolds, facilitating the exploration of novel chemical entities and the advancement of drug development processes.

InChI:InChI=1/C9H6BrN/c10-9-2-1-7-3-4-11-6-8(7)5-9/h1-6H

Upstream product

• 33065-61-1 6-bromo-1H-indene 
• 1009309-65-2 dimethyl(p-bromobenzylidene)aminoacetal 
• 1122-91-4 4-bromo-benzaldehyde 
• 22483-09-6 2,2-dimethoxyethylamine 
• 7664-93-9 sulfuric acid 
• 63927-21-9 (4-bromo-benzylidenamino)-acetaldehyde diethylacetal 
• 1036378-91-2 N-(4-bromo-benzyl)-N-(2,2-dimethoxy-ethyl)-4-methyl-benzenesulfonamide 
• 1036378-89-8 2-(4-bromobenzylamino)acetaldehyde dimethyl aceta 
• 226942-29-6 6-bromo-1,2,3,4-tetrahydroisoquinoline 
• 63927-21-9 (4-bromobenzylidene)-(2,2-diethoxyethyl) amine 
• 34598-50-0 5-bromo-1-indanol 
• 34598-49-7 5-Bromo-1-indanone 

Downstream Products

• 147645-78-1 6-<4-(dibutylamino)phenyl>isoquinoline 
• 173089-82-2 isoquinoline-6-carboxylic acid methyl ester 
• 106778-42-1 isoquinoline-6-carbonitrile 
• 70125-61-0 6-phenylisoquinoline 
• 223671-16-7 6-bromoisoquinoline nitrogen oxide 
• 904324-75-0 [2-(5-isoquinolin-6-yl-pyridin-3-yloxy)-1-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 904324-74-9 [1-cyclohexylmethyl-2-(5-isoquinolin-6-yl-pyridin-3-yloxy)-ethyl]-carbamic acid tert-butyl ester 
• 850197-72-7 5-nitro-6-bromoisoquinoline 
• 675576-26-8 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-isoquinoline 
• 922718-57-8 2-methyl-6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline 
• 922718-55-6 6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline 
• 922718-56-7 2-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-isoquinolinium; iodide 
• 205055-63-6 6-bromo-1-chloroisoquinoline 

Relevant articles and documents

Synthesis of Indole-Dihydroisoquinoline Sulfonyl Ureas via Three-Component Reactions

Isoquinolines activated with sulfamoyl chlorides were reacted with indoles in a 3-component reaction to generate a library of dihydroisoquinoline derivatives. Using a differential protecting group strategy, products could be further derivatised. Synthesis of isoquinoline starting materials using several different methods is also described.

Inhibitors of the detoxifying enzyme of the phytoalexin brassinin based on quinoline and isoquinoline scaffolds

The detoxification of the phytoalexin brassinin to indole-3-carboxaldehyde and S-methyl dithiocarbamate is catalyzed by brassinin oxidase (BOLm), an inducible fungal enzyme produced by the plant pathogen Leptosphaeria maculans. Twenty-six substituted quinolines and isoquinolines are synthesized and evaluated for antifungal activity against L. maculans and inhibition of BOLm. Eleven compounds that inhibit BOLm activity are reported, of which 3-ethyl-6-phenylquinoline displays the highest inhibitory effect. In general, substituted 3-phenylquinolines show significantly higher inhibitory activities than the corresponding 2-phenylquinolines. Overall, these results indicate that the quinoline scaffold is a good lead to design paldoxins (phytoalexin detoxification inhibitors) that inhibit the detoxification of brassinin by L. maculans.

Dehydrogenation of Nitrogen Heterocycles Using Graphene Oxide as a Versatile Metal-Free Catalyst under Air

Graphene oxide (GO) has been developed as an inexpensive, environmental friendly, metal-free carbocatalyst for the dehydrogenation of nitrogen heterocycles. Valuable compounds, such as quinoline, 3,4-dihydroisoquinoline, quinazoline, and indole derivatives, have been successfully used as substrates. The investigation of various oxygen-containing molecules with different conjugated systems indicated that both the oxygen-containing groups and large π-conjugated system in GO sheets are essential for this reaction. (Figure presented.).

CARBONITRILE DERIVATIVES AS SELECTIVE ANDROGEN RECEPTOR MODULATORS

The present invention relates to a compound of Formula 1, 2 or 3: I II III wherein A is N or -CR0--, where R0 is hydrogen, C1-C6 linear or branched chain alkyl, etc., Z is -CRe --, or, -N--, where Re is hydrogen, C1 -C6 linear or branched chain alkyl, etc.; R1 is hydrogen, C1 -C6 linear or branched chain alkyl, etc.; R2 are independently hydrogen or C1-C6 linear or branched chain alkyl; R3 and R4 are independently hydrogen, C1C6 linear or branched chain alkyl, etc.;. R5 and R6 are independently hydrogen or C1-C6 linear or branched chain alkyl, etc.; R8 is hydrogen, C1 -C6 linear or branched chain alkyl, etc.; R9 and R10 are independently hydrogen or C1- C6 linear or branched chain alkyl, etc.; Q is --CO--, --(CH2)q--, --(CHRs)q--, or -(CRsRt)q- -, where Rs and Rt are independently C1-C6 linear or branched chain alkyl, aryl, alkylaryl, heteroaryl or alkylheteroaryl; where q is 0, 1, 2, or 3; and, where n is 0, 1, 2, 3, 4 or 5; or, a pharmaceutically acceptable salt thereof, for the treatment of certain diseases, particularly those affected or mediated by the androgen receptor; to compbinations comprising such compounds with a second pharmaceutically active ingredient; to compositions containing such combinations; and to such combinations for the treatment of various diseases, particularly, those affected or mediated by the androgen receptor.

Luminescent Pt(ii) complexes bearing dual isoquinolinyl pyrazolates: Fundamentals and applications

A series of four Pt(ii) metal complexes with trans-arranged isoquinolinyl azolates have been prepared, [Pt(Lx)2], x = 1-4, (1-4). The associated chelates possess various substituents; namely: one t-butyl (But) at the 6-position (L1), two But groups at the 5,7-positions (L2), one dip (2,6-di-isopropylphenyl) group at the 6-position (L3), and a single dip group at the 4-position of the 1-isoquinolinyl fragment (L4), respectively. Crystal structures of 1 and 4 were determined to shed light on the relationship of photophysics and packing arrangements. Their photophysical properties were measured and compared, for which the solid-state emission spectra of 2 and 4 are nearly identical to the solution spectra of all the Pt(ii) complexes, showing the formation of isolated molecular entities. In contrast, the Pt(ii) complexes 1 and 3 are found to be sensitive to their morphological states and external stimulus. This is confirmed by the gradual red-shifting of the emission with increasing concentration in the PMMA matrix, and the eventual formation of the broadened, metal-metal-to-ligand charge transfer (MMLCT) emission, by (i) wetting with acetone and drying in air, or (ii) grinding with a mortar and pestle, respectively. Organic light-emitting diodes (OLEDs) were also fabricated using multiple layered architecture and lowered doping concentration (e.g. 8 wt%), the latter is for avoiding dopant aggregation in the emitting layer. The associated OLED performances (i.e. ηmax = 11.5%, 8.5%, and 11.2% for 1, 2 and 3) confirmed their suitability and potential as dopants for phosphorescent OLEDs.

ARYL CARBOXAMIDE DERIVATIVES AS SODIUM CHANNEL INHIBITORS FOR TREATMENT OF PAIN

The present invention provides compounds that are inhibitors of voltage-gated sodium channels (Nav), in particular Nav 1.7, and are therefore useful for the treatment of diseases treatable by inhibition of these channels, in particular, chronic pain disorders. Also provided are pharmaceutical compositions containing such compounds and processes for preparing such compounds.

New substituted isoquinoline and isoquinolinone derivatives

The invention relates to 6-substituted isoquinoline and isochinolone derivatives of the formula (I) useful for the treatment and/or prevention of diseases associated with Rho-kinase and/or Rho-kinase mediated phosphorylation of myosin light chain phosphatase, and compositions containing such compounds.

Synthesis of N-substituted benzo[c][1,7]- and benzo[c][1,8] phenanthrolin-(5H)-6-ones through a Pd-mediated Suzuki-Miyaura heteroaryl-aryl coupling reaction

In the course of the search for non-camptothecin topoisomerase I inhibitors we have undertaken the synthesis of N-substituted benzo[c][1,7]- and benzo[c][1,8]phenanthrolinone derivatives. An intermolecular Suzuki-Miyaura heteroaryl-aryl coupling reaction was planned as the key step. Then a nitro reduction followed by a concomitant lactamization achieved the construction of the tetracycle structures. This methodology permitted a rapid and efficient elaboration of biologically potent compounds.

SUBSTITUTED ISOQUINOLINE AND ISOQUINOLINONE DERIVATIVES

The invention relates to 6-substituted isoquinoline and isochinolone derivatives of the formula (I) useful for the treatment and/or prevention of diseases associated with Rho-kinase and/or Rho-kinase mediated phosphorylation of myosin light chain phosphatase, and compositions containing such compounds.

CYCLOALKYLAMINE SUBSTITUTED ISOQUINOLONE AND ISOQUINOLINONE DERIVATIVES

The invention relates to 6-substituted isoquinoline and isoquinolinone derivatives of the formula 1 useful for the treatment and prevention of diseases associated with Rho-kinase and Rho- kinase mediated phosphorylation of myosin light chain phosphatase, and composition containing such compound