| Identification | Back Directory | [Name]
2-BROMO-9H-XANTHEN-9-ONE | [CAS]
56341-31-2 | [Synonyms]
SBB010036
2-BroMoxanthone
2-bromo-9-xanthenone
2-bromoxanthen-9-one
2-BROMO-9H-XANTHEN-9-ONE
2-bromo-1H-xanthen-9-one
9H-Xanthen-9-one, 2-bromo- | [Molecular Formula]
C13H7BrO2 | [MDL Number]
MFCD00089598 | [MOL File]
56341-31-2.mol | [Molecular Weight]
275.1 |
| Chemical Properties | Back Directory | [Melting point ]
150 °C(Solv: ethanol (64-17-5); water (7732-18-5)) | [Boiling point ]
403.2±34.0 °C(Predicted) | [density ]
1.620±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [Appearance]
White to off-white Solid | [InChI]
InChI=1S/C13H7BrO2/c14-8-5-6-12-10(7-8)13(15)9-3-1-2-4-11(9)16-12/h1-7H | [InChIKey]
DYQUGFRRGGOYCA-UHFFFAOYSA-N | [SMILES]
C1(=O)C2=C(C=CC=C2)OC2=C1C=C(Br)C=C2 |
| Hazard Information | Back Directory | [Uses]
2-Bromoxanthone is part of a group of Xanthone (X500100) derivatives that belong to an important class of oxygenated heterocycles that have potential antitumour, antidiabetic and antihypertensive activity. | [Synthesis]
General procedure for the synthesis of 2-bromo-9H-xanthen-9-one from 2-(4-bromophenoxy)benzaldehyde: 2-(4-bromophenoxy)-5-chlorobenzaldehyde (82.8 mg, 0.3 mmol), CuCl?(4.05 mg, 0.03 mmol), and NFSI (189 mg, 0.6 mmol) were added to a 15 mL thick-walled pressure-resistant reaction tube , and 3 mL of acetonitrile was added as solvent. The reaction mixture was magnetically stirred at 100 °C for 24 hours. After completion of the reaction, it was cooled to room temperature, 10 mL of water was added and extracted with dichloromethane (3 x 10 mL). The organic phases were combined and dried with anhydrous Na?SO? After filtration, the product was purified by column chromatography using petroleum ether/ethyl acetate (20:1, v/v) as eluent. The eluate containing the product was collected and evaporation of the solvent gave 2-bromo-9H-xanthen-9-one as a white solid in 70% yield. | [References]
[1] Organic Letters, 2012, vol. 14, # 3, p. 902 - 905
[2] Patent: CN107641111, 2018, A. Location in patent: Paragraph 0066; 0067; 0068
[3] Organic Letters, 2013, vol. 15, # 4, p. 928 - 931
[4] Organic and Biomolecular Chemistry, 2017, vol. 15, # 7, p. 1589 - 1592 |
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