6-BROMO-2,4(1H,3H)-QUINAZOLINEDIONE Chemical Properties

Melting point:

>300

Density 

1.752±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

Solid

pka

10.37±0.20(Predicted)

color 

Off-white

InChI

InChI=1S/C8H5BrN2O2/c9-4-1-2-6-5(3-4)7(12)11-8(13)10-6/h1-3H,(H2,10,11,12,13)

InChIKey

JZDVFUAHGLJVQG-UHFFFAOYSA-N

SMILES

N1C2=C(C=C(Br)C=C2)C(=O)NC1=O

CAS DataBase Reference

88145-89-5

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

RIDADR 

UN2811

HazardClass 

IRRITANT

HS Code 

2933599590

6-BROMO-2,4(1H,3H)-QUINAZOLINEDIONE Usage And Synthesis

Uses

6-Bromoquinazoline-2,4-dione, also known as hexabromoquinazoline-2,4(1H,3H)-dione, is a common derivative of quinazoline-2,4-one. Quinazoline ones are an important class of compounds containing pyrimidine heterocycles. Due to their simple structure and ease of modification, they are important intermediates in fine chemical and pharmaceutical synthesis and are widely used in antibacterial, anti-inflammatory, antihypertensive, anticonvulsant, and antitumor drugs. Quinazoline-2,4-dione derivatives possess excellent biological activities and have been widely used in pesticides and pharmaceuticals, exhibiting bactericidal, herbicidal, insecticidal, anticonvulsant, and neuroprotective activities. Among them, 6-substituted 2,4-quinazoline diones, due to their broad biological activities, can be used as drugs such as anti-HIV agents and protein tyrosine kinase inhibitors, and also as pesticides such as insecticides and fungicides.

Synthesis

General procedure for the synthesis of 6-bromoquinazoline-2,4-dione from carbon dioxide and 2-amino-5-bromobenzonitrile: 2-amino-5-bromobenzonitrile (10 g, 52 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (30 mL, 200 mmol) were dissolved in dimethylformamide (DMF) (50 mL) at The reaction was stirred in a carbon dioxide atmosphere (maintained by an attached latex balloon) under oil bath heating at 100 °C for 48 hours. Upon completion of the reaction, the reaction solution was removed from the heating source and slowly poured into ice bath cooled 1N HCl solution (500 mL) to precipitate a solid. The solid product was collected by filtration, washed with deionized water and dried to give 6-bromo-1H-quinazoline-2,4-dione as a yellow solid (12 g, quantitative yield). Thin layer chromatography (TLC) analysis showed an Rf value of 0.27 (unfolding agent: dichloromethane solution in 5% methanol).1H NMR (DMSO-d6, 300 MHz) δ 11.41 (s, 1H), 11.27 (s, 1H), 7.91 (d, J = 2.3 Hz, 1H), 7.77 (dd, J1 = 8.8 Hz, J2 = 2.3 Hz, 1H), 7.11 (dd, J1 = 8.8 Hz, J2 = 2.3 Hz, 1H), 7.11 (dd, J1 = 2.3 Hz, 2.3 Hz, 2.3 Hz, 1H). 1H), 7.11 (d, J = 8.8 Hz, 1H). Electrospray ionization mass spectrometry (ESI-MS) analysis: m/z calculated value C8H5BrN2O2 [M]+: 240.0; measured value: 241.0 [M+H]+.

References

[1] Patent: WO2004/99159, 2004, A1. Location in patent: Page 34; 58; 68
[2] RSC Advances, 2015, vol. 5, # 7, p. 5032 - 5037
[3] Catalysis Science and Technology, 2016, vol. 6, # 5, p. 1435 - 1441
[4] Tetrahedron, 2018, vol. 74, # 24, p. 2914 - 2920
[5] RSC Advances, 2015, vol. 5, # 20, p. 15668 - 15673

6-BROMO-2,4(1H,3H)-QUINAZOLINEDIONE(88145-89-5)Related Product Information

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