17518-98-8

Basic information

• Product Name: 7-Bromo-6-chloro-4-quinazolinone
• Synonyms: 7-Bromo-6-Chloro-4(3H)-Quinazo;7-Bromo-6-chloro-4-quinazolinone;7-Bromo-6-chloro-4(3H)-quinazolinone;7-BROMO-6-CHLORO-QUINAZOLINE-4(3H)-ONE;7-Bromo-6-chloro-4(1H)-quinazolinone;4(3H)-Quinazolinone, 7-broMo-6-chloro-;7-broMo-6-chloro-3,4-dihydroquinazolin-4-one;7-BroMo-6-chloro-4-quinaz...
• CAS NO: 17518-98-8
• Molecular Formula: C₈H₄BrClN₂O
• Molecular Weight: 259.49
• Product Categories: Heterocycles;Aromatics Compounds;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 17518-98-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: >300°C
• Boiling Point: 481.8 °C at 760 mmHg
• Flash Point: 245.2 °C
• Appearance: yellow-brown solid
• Density: 1.95 g/cm³
• Vapor Pressure: 1.94E-09mmHg at 25°C
• Refractive Index: 1.737
• Storage Temp.: Refrigerator
• Solubility: DMSO
• PKA: -0.55±0.20(Predicted)
• CAS DataBase Reference: 7-Bromo-6-chloro-4-quinazolinone(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Bromo-6-chloro-4-quinazolinone(17518-98-8)
• EPA Substance Registry System: 7-Bromo-6-chloro-4-quinazolinone(17518-98-8)

Safety Data

• Hazardous Substances Data: 17518-98-8(Hazardous Substances Data)

Usage

Description

7-Bromo-6-chloro-4-quinazolinone is an organic compound with the molecular formula C8H4BrClN2O. It is a yellow-brown solid and is known for its significance as an intermediate in the synthesis of various pharmaceutical compounds.

Uses

Used in Pharmaceutical Industry:
7-Bromo-6-chloro-4-quinazolinone is used as an intermediate in the manufacturing process for the anticoccidial drug (coccidiostat) halofuginone (Tempostatin). 7-Bromo-6-chloro-4-quinazolinone plays a crucial role in the development of medications that help combat parasitic infections, particularly coccidiosis, which is a disease affecting poultry and other animals.
The compound's chemical structure and properties make it a valuable building block for the synthesis of other bioactive molecules, potentially expanding its applications in the pharmaceutical industry for the development of new drugs and therapies.

InChI:InChI=1/C8H4BrClN2O/c9-5-2-7-4(1-6(5)10)8(13)12-3-11-7/h1-3H,(H,11,12,13)

Upstream product

• 150812-32-1 2-amino-4-bromo-5-chlorobenzoic acid 
• 3473-63-0 formamidine acetic acid 
• 201230-82-2 carbon monoxide 
• 77287-34-4 formamide 
• 108-41-8 1-chloro-3-methylbenzene 
• 21900-32-3 4-bromo-3-chlorobenzoyl chloride 
• 25118-59-6 4-bromo-3-chlorobenzoic acid 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 1203455-38-2 (2S,3R)-3-benzyloxy-2-[2-oxo-3-(7-bromo-6-chloro-4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl ester 
• 1203455-28-0 (2R,3S)-3-benzyloxy-2-[2-oxo-3-(7-bromo-6-chloro-4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl ester 
• 1260847-61-7 7-bromo-4, 6-dichloroquinazoline 
• 17395-31-2 halofuginone hydrobromide 
• 64544-01-0 7-bromo-6-chloro-3-[3-(3-hydroxyl-2-piperidyl)-2-oxopropyl]quinazolin-4(3H)-one 

Relevant articles and documents

A convergent strategy towards febrifugine and related compounds

We report a modular five step synthetic route to the febrifugines that employs 2-(chloromethyl)allyl-trimethylsilane as a conjunctive reagent for the coupling of the piperidine and quinazolinone groups. We also demonstrate the application of a recent Rh-catalyzed quinazolinone synthesis for the facile generation of febrifugine analogs.

A novel synthesis of the efficient anti-coccidial drug halofuginone hydrobromide

Background: Halofuginone hydrobromide (1) is recognized as an effective drug against several species of Eimeria (E.) in poultry. In this paper, we describe a convenient and low cost preparation method for the compound, as well as primary validation of its activity. Methods: First, 7-bromo-6-chloroquinazolin-4(3H)-one (2) was prepared from m-chlorotoluene by a conventional process, and then chloroacetone was creatively introduced in two steps. Finally, halofuginone hydrobromide (1) was obtained from 7-bromo-6-chloro-3-(3-cholroacetonyl) quinazolin-4(3H)-one (4) by a four-step reaction sequence including condensation, cyclization, deprotection and isomerization. The structures of the relative intermediates and target compound were characterized by melting point, IR, MS and 1H-NMR. Besides, the protective effect of compound 1-supplemented chicken diet at doses of 6, 3 and 1.5 mg per 1 kg were evaluated on chickens infected with E. tenella, by reduction in mortality, weight loss, fecal oocyst excretion and gut pathology, respectively. Results: Halofuginone hydrobromide (1) was prepared successfully by and improved and innovative method based on traditional research. Moreover, the synthesized halofuginone hydrobromide significantly exhibited an anti-coccidial property. Conclusions: The fruitful work described in this Communication has resulted in halofuginone hydrobromide, which has a good pharmaceutical development prospects, becoming more available for large-scale production.

INHIBITORS OF KRAS G12C

Compounds having activity as inhibitors of G12C mutant KRAS protein are provided. The compounds have the following structure (I): or a pharmaceutically acceptable salt, tautomer, prodrug or stereoisomer thereof, wherein R1, R2a, R3a, R3b, R4a, R4b, G1, G2, L1, L2, m1, m2, A, B, W, X, Y, Z and E are as defined herein. Methods associated with preparation and use of such compounds, pharmaceutical compositions comprising such compounds and methods to modulate the activity of G12C mutant KRAS protein for treatment of disorders, such as cancer, are also provided.