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

Chemical Properties

Yellow-Brown Solid

Uses

7-Bromo-6-chloro-4(3H)-quinazolinone is an important intermediate in the manufacturing of the anticoccidial drug (coccidiostat) halofuginone (Tempostatin).

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

• 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 
• 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 

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.

The drug intermediate halofuginone, fruits alkone parent nucleus synthesis method

The invention discloses a drug intermediate of halofuginone and a synthesis method of a halofuginone parent nucleus. The structural formula of the intermediate is disclosed in the specification. The synthesis method of the halofuginone parent nucleus is characterized by comprising the following steps: 1) in the presence of a catalyst, heating 3-bromo-4-chloroaniline and trimethyl orthoformate to sufficiently react, cooling, sufficiently reacting with NH3, separating, and carrying out primary purification to obtain a solid crude product; and 2) in the presence of a catalyst, sufficiently heating the obtained solid, acetic acid, CO and O2 to react, separating and purifying to obtain the end product. The synthesis method is a two-step process, and has the advantages of simple technique, environment friendliness, high yield and very low cost since the raw materials are accessible 3-bromo-4-chloroaniline and trimethyl orthoformate.

A Mild and Regioselective Route to Functionalized Quinazolines

A Rh-catalyzed ortho-amidation cyclocondensation sequence gave a range of 4-aminoquinazolines in high yield. The method features a remarkably mild C(sp2)-H activation step and can be exploited to rapidly access compounds with established biological activity.