102393-82-8

Basic information

• Product Name: 6-BROMO-2,4-DICHLOROQUINAZOLINE
• Synonyms: 6-BROMO-2,4-DICHLOROQUINAZOLINE;6-Bromo-2,4-dichloroquina...;2,4-Dichloro-6-broMoquinazoline;4-dichloroquinazoline;6-broMo-2,4-dichlroquinazoline
• CAS NO: 102393-82-8
• Molecular Formula: C₈H₃BrCl₂N₂
• Molecular Weight: 277.93282
• Product Categories: CHIRAL CHEMICALS
• Mol File: 102393-82-8.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 330.155 °C at 760 mmHg
• Flash Point: 153.473 °C
• Appearance: Off-white/Solid
• Density: 1.852 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.696
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: -1.19±0.30(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 6-BROMO-2,4-DICHLOROQUINAZOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-2,4-DICHLOROQUINAZOLINE(102393-82-8)
• EPA Substance Registry System: 6-BROMO-2,4-DICHLOROQUINAZOLINE(102393-82-8)

Safety Data

• Hazardous Substances Data: 102393-82-8(Hazardous Substances Data)

Usage

Description

6-BROMO-2,4-DICHLOROQUINAZOLINE is a chemical compound characterized by its quinazolines structure, with a bromo and two chloro substituents. It is a significant intermediate in the synthesis of various organic compounds and has potential applications in different industries due to its unique chemical properties.

Uses

Used in Organic Synthesis:
6-BROMO-2,4-DICHLOROQUINAZOLINE is used as a key intermediate for the synthesis of a wide range of organic compounds. Its unique structure allows for further functionalization and modification, making it a valuable building block in the development of new molecules with diverse applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 6-BROMO-2,4-DICHLOROQUINAZOLINE is used as a crucial intermediate in the development of new drugs. Its chemical properties enable the creation of novel therapeutic agents with potential applications in various medical fields.
Used in Agrochemicals:
6-BROMO-2,4-DICHLOROQUINAZOLINE is also utilized in the agrochemical industry as a vital raw material for the synthesis of various agrochemical products. Its unique structure contributes to the development of new compounds with improved efficacy and selectivity in crop protection and pest management.
Used in Dyestuff Industry:
In the dyestuff industry, 6-BROMO-2,4-DICHLOROQUINAZOLINE serves as an essential intermediate for the production of various dyes and pigments. Its chemical properties allow for the creation of new colorants with enhanced properties, such as improved color strength, stability, and fastness.

Synthesis

The synthesis of?6-BROMO-2,4-DICHLOROQUINAZOLINE is as follows:BTC (0.65 g, 2.2 mmol in 6mL of PhCl) was added to astirred solution of tris(4-methoxyphenyl)phosphine oxide 3d(0.33 g, 0.9 mmol in 5mL PhCl) dropwise in a round botttomflask placed on an ice bath. After complete addition,the mixture was stirred for 30 min at room temperature.Then isatin-3-oximes (3 mmol) were added, and the mixturewas heated to 120 C until completion of the reaction(followed by TLC, n-hexane/ethyl acetate 10:1). Aftercooling, the mixture was then poured into 50mL ice waterand extracted with ethyl acetate (320 mL). The organiclayer was dried over anhydrous Na2SO4 and concentrated invacuo. The crude product was purified over column chromatography(n-hexane/ethyl acetate 10:1) to afford thepure produce 2,4-dichloroquinazolins. Tris(4-methoxyphenyl)phosphine oxide 3d was recovered by column chromatography(n-hexane/ethyl acetate 1:1).

InChI:InChI=1/C8H3BrCl2N2/c9-4-1-2-6-5(3-4)7(10)13-8(11)12-6/h1-3H

Upstream product

• 88145-89-5 6-bromo-1H-quinazoline-2,4-dione 
• 49675-78-7 5-bromo-3-(hydroxyimino)indolin-2-one 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 39263-32-6 2-amino-5-bromobenzonitrile 
• 88145-89-5 6-bromo-quinazoline-2,4-diol 
• 24088-82-2 6-bromo-2H-[1,3]benzoxazine-2,4(3H)dione 
• 5794-88-7 5-Bromo-2-aminobenzoic acid 
• 106-40-1 4-bromo-aniline 
• 66416-72-6 4-bromo-2-iodoaniline 
• 878133-05-2 N-(4-bromo-2-iodophenyl)-2,2,2-trifluoroacetamide 
• 52727-57-8 5-bromo-2-aminobenzoic acid methyl ester 
• 503-38-8 trichloromethyl chloroformate 
• 16313-66-9 5-bromoanthranilamide 
• 57-13-6 urea 

Downstream Products

• 111218-89-4 6-bromo-2-chloroquinazolin-4-amine 

Relevant articles and documents

One-pot cascade ring enlargement of isatin-3-oximes to 2,4-dichloroquinazolines mediated by bis(trichloromethyl)carbonate and triarylphosphine oxide

An efficient and convenient one-pot cascade synthesis of 2,4-dichloroquinazolines directly from isatin-3-oximes with the addition of bis(trichloromethyl)carbonate and triarylphosphine oxide was developed, leading to substituted quinazolines in moderate to excellent yields. The efficiency of this transformation was demonstrated by compatibility with a range of functional groups. Thus, the method represents a convenient and practical strategy for the synthesis of substituted 2,4-dichloroquinazolines.

Discovery and in vivo effects of novel human natriuretic peptide receptor A (NPR-A) agonists with improved activity for rat NPR-A

Natriuretic peptide receptor A (NPR-A) agonists were evaluated in vivo by optimizing the structure of quinazoline derivatives to improve agonistic activity for rat NPR-A. A 1,4-Cis-aminocyclohexylurea moiety at 4-position and hydroxy group of D-alaninol at 2-position on the quinazoline ring were found to be important factors in improving rat NPR-A activity. We identified potent quinazoline and pyrido[2,3-d]pyrimidine derivatives against rat NPR-A, with double-digit nanomolar EC50 values. The in vivo results showed that compound 56b administered at 1.0 mg/kg/min significantly increased plasma cGMP concentration and urine volume in rats. We discovered novel potent NPR-A agonists that showed agonistic effects similar to those of atrial natriuretic peptide.

DIARYLTHIOHYDANTOIN COMPOUND AS ANDROGEN RECEPTOR ANTAGONIST

The present application belongs to the field of medicine. In particular, the present application relates to a diarylthiohydantoin compound as an androgen receptor antagonist or a pharmaceutically acceptable salt thereof, a preparation method of the same, a pharmaceutical composition comprising the compound, and a use thereof in treating a cell proliferative disease mediated by androgen. The compound of the present application has good antagonistic effect on androgen receptor and exhibits excellent antitumor effect.

Discovery and SAR of a novel series of Natriuretic Peptide Receptor-A (NPR-A) agonists

Novel thienopyrimidine compounds 2 and 3 were discovered from high-throughput screening as Natriuretic Peptide Receptor A (NPR-A) agonists. Scaffold hopping of a thienopyrimidine ring to a quinazoline ring, introduction of the basic functional group and optimization of the substituent on the 6-position of the benzene ring of quinazoline led to improved agonistic activity. We discovered compound 48, which showed potent agonistic activity for NPR-A with an EC50 value of 0.073 μM, indicating 350-fold potency compared to the hit compound 3.