205055-63-6

Basic information

• Product Name: 6-Bromo-1-chloroisoquinoline
• Synonyms: 6-BROMO-1-CHLORO-ISOQUINOLINE;1-Chloro-6-bromoisoquinoline;1-chloro -6-broMideisoquinoline;6-Bromo-1-chloroisoquinoline 1-Chloro-6-bromoisoquinoline;Isoquinoline, 6-bromo-1-chloro-
• CAS NO: 205055-63-6
• Molecular Formula: C₉H₅BrClN
• Molecular Weight: 242.5
• EINECS: -0
• Product Categories: Quinoline series;Building Blocks;Isoquinoline
• Mol File: 205055-63-6.mol

Chemical Properties

• Boiling Point: 349.497 °C at 760 mmHg
• Flash Point: 165.17 °C
• Appearance: /
• Density: 1.673
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.68
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 1.48±0.38(Predicted)
• CAS DataBase Reference: 6-Bromo-1-chloroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromo-1-chloroisoquinoline(205055-63-6)
• EPA Substance Registry System: 6-Bromo-1-chloroisoquinoline(205055-63-6)

Safety Data

• Hazard Codes: T
• Statements: 25-38-41
• Safety Statements: 26-45
• RIDADR: UN2811
• Hazardous Substances Data: 205055-63-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Bromo-1-chloroisoquinoline is used as a reactant for the preparation of phenylimidazoles, which serve as Smoothened antagonists. These antagonists are significant in the development of drugs targeting the Smoothened protein, a key component in the Hedgehog signaling pathway. This pathway is involved in various cellular processes, and its dysregulation has been associated with several cancers and congenital disorders. By acting as a reactant in the synthesis of these antagonists, 6-Bromo-1-chloroisoquinoline plays a crucial role in the development of potential therapeutic agents for such conditions.

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

Upstream product

• 82827-09-6 6-bromo-2H-isoquinoline-1-one 
• 223671-16-7 6-bromoisoquinoline nitrogen oxide 
• 34784-05-9 6-bromo-isoquinoline 
• 119-65-3 isoquinoline 

Downstream Products

• 215453-25-1 6-Bromo-1-phenoxyisoquinoline 
• 215453-26-2 (6-bromoisoquinolin-1-yl)amine 
• 552331-12-1 (6-bromo-isoquinolin-1-yl)-carbamic acid tert-butyl ester 
• 82827-09-6 6-bromo-2H-isoquinoline-1-one 
• 1541185-71-0 (S)-5-{6-[4-(2H-pyrazol-3-yl)phenoxy]isoquinolin-1-yloxymethyl}pyrrolidin-2-one 
• 1541189-39-2 C₂₉H₃₄N₄O₄Si 
• 1541189-38-1 C₁₄H₁₃BrN₂O₂ 

Relevant articles and documents

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A Rho-associated protein kinase (ROCK) inhibitor represented by formula (I), a pharmaceutical composition comprising same, and a use thereof for preventing or treating ROCK-mediated diseases.

Synthetic method of drug intermediate nitrogen-containing heterocycle-containing brominated compound

The invention relates to a method for synthesizing a pharmaceutical intermediate nitrogen heterocyclic bromo-compound. The method comprises that 6-bromoisoquinoline, dichloromethane and m-chloroperoxybenzoic acid as raw materials undergo a reaction to produce a mixture 6-bromoisoquine oxynitride, phosphorus oxychloride is added into the mixture so that solid and water phase products are obtained,the solid products are dried, the water phase products are repeatedly washed and are extracted multiple times, the organic phase is spin-dried, the solid and water phases are treated so that 6-bromo-1-chloroisoquinoline is obtained, the solid crude product and the water crude product are mixed, the mixture is treated through a silica gel column of 100-200 meshes, the mixture is eluted through a petroleum ether PE: ethyl acetate EA eluent A to form a pure product 6-bromo-1-chloroisoquinoline, trimethylbromosilane, acetonitrile and 6-bromo-1-chloroisoquinoline undergo a reaction, pH of the reaction product is adjusted to 7 so that 1, 6-dibromoisoquinoline is obtained, and the 1, 6-dibromoisoquinoline is added into dichloroditriphenyl phosphine and a homemade Grignard reagent so that a finalproduct 6-bromo-1-methylisoquinoline is obtained. The method has the advantages of clear processes, less waste, high yield, raw material saving and operation easiness.

The discovery of VU0652957 (VU2957, Valiglurax): SAR and DMPK challenges en route to an mGlu4 PAM development candidate

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Method for preparing 2-methyl-1-oxo-1, 2-dihydroisoquinolines-6-formic acid

The invention relates to a method for synthesizing 2-methyl-1-oxo-1, 2-dihydroisoquinolines-6-formic acid. The 2-methyl-1-oxo-1, 2-dihydroisoquinolines-6-formic acid is made of 6-bromoisoquinoline. The method includes adding meta-chloroperoxybenzoic acid into the 6-bromoisoquinoline and carrying out reaction on the 6-bromoisoquinoline and the meta-chloroperoxybenzoic acid under room-temperature conditions overnight to obtain a mixture which is bromoisoquinoline nitrogen oxide; adding the mixture into phosphoryl chloride in batches, carrying out temperature reaction on the mixture and the phosphoryl chloride to obtain reaction products, cooling the reaction products to precipitate a large quantity of solid and washing and drying the solid to obtain 6-bromine-1-chloroisoquinoline; extracting aqueous phases and directly carrying out spin dry on organic phases to obtain 6-bromine-1-chloroisoquinoline with the purity higher than 95%; placing the 6-bromine-1-chloroisoquinoline into THF (tetrahydrofuran) and adding n-butyl lithium and carbon dioxide gas into the 6-bromine-1-chloroisoquinoline and the THF to obtain 1-chloroisoquinoline-6-formic acid; placing the 1-chloroisoquinoline-6-formic acid into concentrated hydrochloric acid to obtain white solid which is 1-oxo-1, 2-dihydroisoquinolines-6-formic acid; placing the 1-oxo-1, 2-dihydroisoquinolines-6-formic acid into solvents, adding cesium carbonate into the 1-oxo-1, 2-dihydroisoquinolines-6-formic acid and the solvents and dropwise adding methyl iodide into the 1-oxo-1, 2-dihydroisoquinolines-6-formic acid and the solvents to obtain 2-methyl-1-oxo-1, 2-dihydroisoquinolines-6-methyl formate; adding the 2-methyl-1-oxo-1, 2-dihydroisoquinolines-6-methyl formate into methyl alcohol, adding NaOH solution into the 2-methyl-1-oxo-1, 2-dihydroisoquinolines-6-methyl formate and the methyl alcohol, removing the methyl alcohol by means of reduced-pressure distillation to obtain mixtures, regulating the PH (potential of hydrogen) of the mixtures until the PH of the mixtures is equal to 2, precipitating solid, carrying out suction filtration and washing and drying the solid to obtain a product which is the 2-methyl-1-oxo-1, 2-dihydroisoquinolines-6-formic acid. The method has the advantages of reasonable route, little wastage, high yield, easiness in operation and capability of saving raw materials.

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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.

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The present invention relates to novel imidazoisoquinoline compounds of the formula I and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof wherein A1 is N or C(R2), A2 is N or C(R3); A3 is N or C(R4); A4 is N or C(R5); A5 is N or C(R6); and where Ar, R, R1, R2, R3, R4,R5 and R6 are as defined in the claims. The compounds of formula (I), as well as the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof, are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

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