| Identification | Back Directory | [Name]
6-BROMO-2,4(1H,3H)-QUINAZOLINEDIONE | [CAS]
88145-89-5 | [Synonyms]
6-Bromoquinazoline-2,4-dione
6-broMo-1,2,3,4-tetrahydroquin
6-bromo-1H-quinazoline-2,4-dione
6-BROMO-2,4(1H,3H)-QUINAZOLINEDIONE
6-Bromo-1H,3H-quinazoline-2,4-dione
6-bromoquinazoline-2,4(1H,3H)-dione
2,4(1H,3H)-Quinazolinedione, 6-bromo-
6-Bromoquinazoline-2,4(1H,3H)-dione,97%
6-broMo-1,2,3,4-tetrahydroquinazoline-2,4-dione | [Molecular Formula]
C8H5BrN2O2 | [MDL Number]
MFCD00462868 | [MOL File]
88145-89-5.mol | [Molecular Weight]
241.04 |
| Chemical Properties | Back Directory | [Melting point ]
>300 | [density ]
1.752±0.06 g/cm3(Predicted) | [storage temp. ]
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 |
| Hazard Information | Back Directory | [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 |
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