223671-15-6

Basic information

• Product Name: 7-BROMO-1-HYDROXYISOQUINOLINE
• Synonyms: 7-BROMO-1-HYDROXYISOQUINOLINE;7-Bromoisocarbostyril;7-BROMO-1-HYDROXYISOQUINOLINE, 98+%;7-bromoisoquinolin-1-ol;7-BroMoisoquinolin-1-one;7-Bromo-1(2H)-isoquinolinone;7-broMoisoquinolin-1(2H)-one;7-Bromoisoquinolin-1-ol, 7-Bromo-1-hydroxy-2-azanaphthalene
• CAS NO: 223671-15-6
• Molecular Formula: C₉H₆BrNO
• Molecular Weight: 224.05
• EINECS: -0
• Product Categories: Building Blocks;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Isoquinolines;in stock
• Mol File: 223671-15-6.mol

Chemical Properties

• Melting Point: 248-250°C
• Boiling Point: 427.5 °C at 760 mmHg
• Flash Point: 212.4 °C
• Appearance: /
• Density: 1.620±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 1.63E-07mmHg at 25°C
• Refractive Index: 1.63
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 12.34±0.20(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 8405244
• CAS DataBase Reference: 7-BROMO-1-HYDROXYISOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-BROMO-1-HYDROXYISOQUINOLINE(223671-15-6)
• EPA Substance Registry System: 7-BROMO-1-HYDROXYISOQUINOLINE(223671-15-6)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-41-37/38-22
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 223671-15-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
7-BROMO-1-HYDROXYISOQUINOLINE is used as a pharmaceutical intermediate for the development and synthesis of various drugs. Its unique chemical structure allows it to be a versatile building block in the creation of new medications with potential therapeutic applications.
Additionally, 7-BROMO-1-HYDROXYISOQUINOLINE is used to prepare 1-amino-4-bromoisoquinoline, which is another important compound in the pharmaceutical industry. 7-BROMO-1-HYDROXYISOQUINOLINE can be further utilized in the synthesis of various drugs with specific therapeutic properties.

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

Upstream product

• 1200-07-3 trans-4-bromocinnamic acid 
• 27465-66-3 4-bromocinnamoyl chloride 
• 58794-09-5 7-bromoisoquinoline 
• 108-05-4 vinyl acetate 
• 1427180-45-7 (3-bromophenyl)formamido 2,2-dimethylpropanoate 
• 585-76-2 m-bromobenzoic acid 
• 1711-09-7 3-bromobenzoyl chloride 
• 1122-91-4 4-bromo-benzaldehyde 
• 215453-51-3 7-bromo-1-chloroisoquinoline 
• 223671-18-9 7-bromo-isoquinoline N-oxide 

Downstream Products

• 444898-46-8 C₃₅H₂₆BrNO₈ 
• 658081-95-9 4-(7-bromo-1-oxo-1H-isoquinolin-2-ylmethyl)-benzoic acid tert-butyl ester 
• 658082-39-4 methyl 1-oxo-2H-isoquinoline-7-carboxylate 
• 256477-77-7 1,4-dichloro-7-isoquinolinecarbonyl chloride 
• 223671-87-2 7-bromo-4-chloro-2H-isoquinolin-1-one 
• 1372889-99-0 methyl 2-benzyl-1-oxo-1,2-dihydroisoquinoline-7-carboxylate 
• 1372890-00-0 methyl 2-(4-methoxyphenyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate 
• 1372890-24-8 methyl 2-[3-(4-methoxyphenoxy)propyl]-1-oxo-1,2-dihydroisoquinoline-7-carboxylate 
• 1372890-26-0 methyl 2-[2-(4-methoxyphenoxy)ethyl]-1-oxo-1,2-dihydroisoquinoline-7-carboxylate 
• 1372890-33-9 methyl 2-{2-[(4-methoxyphenyl)amino]ethyl}-1-oxo-1,2-dihydroisoquinoline-7-carboxylate 
• 1372890-37-3 methyl 2-[3-(bromomethyl)benzyl]-1-oxo-1,2-dihydroisoquinoline-7-carboxylate 
• 1372890-38-4 methyl 2-{3-[(diethylamino)methyl]benzyl}-1-oxo-1,2-dihydroisoquinoline-7-carboxylate 
• 1372890-53-3 methyl 1-oxo-2-(2-{[3-(1H-pyrazol-1-yl)phenyl]amino}ethyl)-1,2-dihydroisoquinoline-7-carboxylate 
• 1372890-54-4 methyl 2-(2-{(cyclopropylcarbonyl)[3-(1H-pyrazol-1-yl)phenyl]amino}ethyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate 

Relevant articles and documents

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.

C(sp2)-H Trifluoromethylation of enamides using TMSCF3: Access to trifluoromethylated isoindolinones, isoquinolinones, 2-pyridinones and other heterocycles

A method for the direct C(sp2)-H trifluoromethylation of enamides, including biologically relevant isoindolinones, isoquinolinones and 2-pyridinones using TMSCF3 under oxidative conditions is presented. The protocol is convenient, operationally simple and exhibits high tolerance across a multitude of relevant handles and functional groups.

DGAT1 INHIBITOR AND PREPARATION METHOD AND USE THEREOF

The present invention discloses a novel DGAT1 inhibitor, especially the compound of formula (I) or a pharmaceutically acceptable salt thereof, preparation and pharmaceutical composition thereof, as well as their uses in the preparation of a medicament for the prevention and treatment of Familial hyperchylomicronemia (FCS), obesity, hyperlipoproteinemia or hypertriglyceridemia.

Artificial Ligands of Streptavidin (ALiS): Discovery, Characterization, and Application for Reversible Control of Intracellular Protein Transport

Artificial ligands of streptavidin (ALiS) with association constants of 106 M-1 were discovered by high-throughput screening of our chemical library, and their binding characteristics, including X-ray crystal structure of the streptavidin complex, were determined. Unlike biotin and its derivatives, ALiS exhibits fast dissociation kinetics and excellent cell permeability. The streptavidin-ALiS system provides a novel, practical compound-dependent methodology for repeated reversible cycling of protein localization between intracellular organella.

Protozoan Parasite Growth Inhibitors Discovered by Cross-Screening Yield Potent Scaffolds for Lead Discovery

Tropical protozoal infections are a significant cause of morbidity and mortality worldwide; four in particular (human African trypanosomiasis (HAT), Chagas disease, cutaneous leishmaniasis, and malaria) have an estimated combined burden of over 87 million disability-adjusted life years. New drugs are needed for each of these diseases. Building on the previous identification of NEU-617 (1) as a potent and nontoxic inhibitor of proliferation for the HAT pathogen (Trypanosoma brucei), we have now tested this class of analogs against other protozoal species: T. cruzi (Chagas disease), Leishmania major (cutaneous leishmaniasis), and Plasmodium falciparum (malaria). Based on hits identified in this screening campaign, we describe the preparation of several replacements for the quinazoline scaffold and report these inhibitors' biological activities against these parasites. In doing this, we have identified several potent proliferation inhibitors for each pathogen, such as 4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-6-(4-((4-methyl-1,4-diazepan-1-yl)sulfonyl)phenyl)quinoline-3-carbonitrile (NEU-924, 83) for T. cruzi and N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-7-(4-((4-methyl-1,4-diazepan-1-yl)sulfonyl)phenyl)cinnolin-4-amine (NEU-1017, 68) for L. major and P. falciparum.

Rhodium(III)-catalyzed C-H activation/annulation with vinyl esters as an acetylene equivalent

The behavior of electron-rich alkenes in rhodium-catalyzed C-H activation/annulation reactions is investigated. Vinyl acetate emerges as a convenient acetylene equivalent, facilitating the synthesis of sixteen 3,4-unsubstituted isoquinolones, as well as select heteroaryl-fused pyridones. The complementary regiochemical preferences of enol ethers versus enol esters/enamides is discussed.

Selective urokinase-type plasminogen activator inhibitors. 4. 1-(7-Sulfonamidoisoquinolinyl)guanidines

1-Isoquinolinylguanidines were previously disclosed as potent and selective inhibitors of urokinase-type plasminogen activator (uPA). Further investigation of this template has revealed that incorporation of a 7-sulfonamide group furnishes a new series of potent and highly selective uPA inhibitors. Potency and selectivity can be achieved with sulfonamides derived from a variety of amines and is further enhanced by the incorporation of sulfonamides derived from amino acids. The binding mode of these 1-isoquinolinylguanidines has been investigated by X-ray cocrystallization studies. uPA inhibitor 26 was selected for further evaluation based on its excellent enzyme potency (Ki 10 nM) and selectivity profile (4000-fold versus tPA and 2700-fold versus plasmin). In vitro, compound 26 is able to inhibit exogenous uPA in human chronic wound fluid (IC50 = 0.89 μM). In vivo, in a porcine acute excisional wound model, following topical delivery, compound 26 is able to penetrate into pig wounds and inhibit exogenous uPA activity with no adverse effect on wound healing parameters. On the basis of this profile, compound 26 (UK-371,804) was selected as a candidate for further preclinical evaluation for the treatment of chronic dermal ulcers.

A convenient synthesis of 1-amino-7-(piperidin-4-yl)isoquinoline

An optimized synthesis of 2-amino-7-(piperidin-4-yl)isoquinoline, starting from 4-bromocinnamic acid, was developed.

Selective urokinase-type plasminogen activator (uPA) inhibitors. Part 3: 1-Isoquinolinylguanidines

A series of 1-isoquinolinylguanidines are shown to be potent inhibitors of uPA with selectivity over tPA and plasmin. Potency is enhanced by the presence of a 4-halo and a 7-aryl substituent, particularly when substituted by a 3-carboxylic acid group. Compound 13j (UK-356,202) combines excellent potency and selectivity, and has been selected as a candidate for clinical evaluation.

1-aroyl-piperidinyl benzamidines

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