66728-98-1

Basic information

• Product Name: 4-Bromo-1-chloroisoquinoline
• Synonyms: 4-BROMO-1-CHLOROISOQUINOLINE;1-Chloro-4-bromoisoquinoline;4-Bromo-1-chloro-2-azanaphthalene
• CAS NO: 66728-98-1
• Molecular Formula: C₉H₅BrClN
• Molecular Weight: 242.5
• EINECS: -0
• Product Categories: CHIRAL CHEMICALS
• Mol File: 66728-98-1.mol
• Article Data: 10

Chemical Properties

• Melting Point: 97 °C (decomp)
• Boiling Point: 328.8°C at 760 mmHg
• Flash Point: 152.6°C
• Appearance: /
• Density: 1.673g/cm³
• Vapor Pressure: 0.000354mmHg at 25°C
• Refractive Index: 1.68
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -0.02±0.31(Predicted)
• CAS DataBase Reference: 4-Bromo-1-chloroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-1-chloroisoquinoline(66728-98-1)
• EPA Substance Registry System: 4-Bromo-1-chloroisoquinoline(66728-98-1)

Safety Data

• Hazardous Substances Data: 66728-98-1(Hazardous Substances Data)

Usage

General Description

4-Bromo-1-chloroisoquinoline, also known as 1-bromo-4-chloroisoquinoline, is a chemical compound with the molecular formula C9H5BrClN. It is a heterocyclic compound with a fused-ring structure that contains both bromine and chlorine atoms. 4-Bromo-1-chloroisoquinoline is commonly used as a building block or intermediate in the synthesis of various pharmaceuticals and agrochemicals. It is also used as a reagent in organic chemistry reactions, particularly in the formation of carbon-carbon and carbon-heteroatom bonds. 4-Bromo-1-chloroisoquinoline is typically handled and stored under controlled conditions due to its potential hazards and reactivity.

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

Upstream product

• 491-30-5 1-hydroxyisoquinoline 
• 3951-95-9 4-Bromo-1-hydroxyisoquinoline 
• 491-30-5 1-isoquinolone 
• 1532-97-4 4-bromoisoquinoline 
• 3951-95-9 4-bromo-1,2-dihydroisoquinolin-1-one 
• 19493-44-8 1-chloroisoquinoline 
• 3749-21-1 4-bromoisoquinoline N-oxide 

Downstream Products

• 746668-73-5 4-bromo-1-methoxyisoqionoline 
• 351324-72-6 1-chloroisoquinoline-4-carbaldehyde 
• 1005772-69-9 1-methoxy-4-isoquinolinecarboxaldehyde 
• 1057681-00-1 6-[4-(1-benzylisoquinolin-4-yl)piperazin-1-yl]nicotinonitrile 
• 1374249-66-7 4-bromo-1-{4-(methoxycarbonyl)phenylcarbonyl}isoquinoline 
• 1353487-23-6 2-[1-[4-[2-(4-chlorophenyl)ethylcarbamoyl]benzoyl]isoquinolin-4-yl]oxyacetic acid 
• 1374249-71-4 tert-butyl 1-(4-{2-[(4-chlorophenyl)ethylamino]carbonyl}phenylcarbonyl)isoquinolin-4-yloxyacetate 
• 1374249-70-3 tert-butyl 1-[4-(carboxy)phenylcarbonyl]isoquinolin-4-yloxyacetate 
• 1374249-69-0 tert-butyl 1-[4-(methoxycarbonyl)phenylcarbonyl]isoquinolin-4-yloxyacetate 
• 1374249-68-9 4-hydroxy-1-{4-(methoxycarbonyl)phenylcarbonyl}isoquinoline 
• 1374249-67-8 1-{4-(methoxycarbonyl)phenylcarbonyl}-4-(3,3,5,5,-tetramethyl-2,5-dioxaborolidin-1-y1)isoquinoline 
• 848841-61-2 4-benzyloxy-6-(1-chloro-isoquinolin-4-yl)-quinazoline 
• 374555-10-9 1-chloro-4-benzylisoquinoline 
• 1071541-73-5 4-(4-bromoisoquinolin-1-ylamino)phenol hydrochloride 

Relevant articles and documents

Discovery and biological evaluation of phthalazines as novel non-kinase TGFβ pathway inhibitors

TGFβ is crucial for the homeostasis of epithelial and neural tissues, wound repair, and regulating immune responses. Its dysregulation is associated with a vast number of diseases, of which modifying the tumor microenvironment is one of vital clinical interest. Despite various attempts, there is still no FDA-approved therapy to inhibit the TGFβ pathway. Major mainstream approaches involve impairment of the TGFβ pathway via inhibition of the TGFβRI kinase. With the purpose to identify non-receptor kinase-based inhibitors to impair TGFβ signaling, an in-house chemical library was enriched, through a computational study, to eliminate TGFβRI kinase activity. Selected compounds were screened against a cell line engineered with a firefly luciferase gene under TGFβ-Smad-dependent transcriptional control. Results indicated moderate potency for a molecule with phthalazine core against TGFβ-Smad signaling. A series of phthalazine compounds were synthesized and evaluated for potency. The most promising compound (10p) exhibited an IC50 of 0.11 ± 0.02 μM and was confirmed to be non-cytotoxic up to 12 μM, with a selectivity index of approximately 112-fold. Simultaneously, 10p was confirmed to reduce the Smad phosphorylation using Western blot without exhibiting inhibition on the TGFβRI enzyme. This study identified a novel small-molecule scaffold that targets the TGFβ pathway via a non-receptor-kinase mechanism.

Novel 3-methylindoline inhibitors of EZH2: Design, synthesis and SAR

EZH2 (enhancer of zeste homologue 2) is the catalytic subunit of the polycomb repressive complex 2 (PRC2) that catalyzes the methylation of lysine 27 of histone H3 (H3K27). Dysregulation of EZH2 activity is associated with several human cancers and theref

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.