| Identification | Back Directory | [Name]
6-BROMO-2H-1,4-BENZOXAZIN-3(4H)-ONE | [CAS]
24036-52-0 | [Synonyms]
24036-52-0
6-Bromo-1,4-benzoxazin-3-one
6-bromo-4H-1,4-benzoxazin-3-one
6-Bromo-4H-benzo[1,4]oxazin-3-one
6-BROMO-3-OXO-4H-BENZO[1,4]OXAZINE
6-BROMO-2H-1,4-BENZOXAZIN-3(4H)-ONE
2H-1,4-Benzoxazin-3(4H)-one, 6-bromo-
6-BROMO-(2H)-1,4-BENZOXAZINE-3(4H)-ONE
6-Bromo-2H-benzo[b][1,4]oxazin-3(4H)-one
JR-8231, 6-Bromo-2H-[1,4]benzoxazin-3(4H)-one, 97% | [Molecular Formula]
C8H6BrNO2 | [MDL Number]
MFCD00461173 | [MOL File]
24036-52-0.mol | [Molecular Weight]
228.04 |
| Chemical Properties | Back Directory | [Melting point ]
220-225 °C
| [Boiling point ]
376.8±42.0 °C(Predicted) | [density ]
1.676 | [storage temp. ]
Room temperature. | [solubility ]
DMSO, Methanol | [form ]
Solid | [pka]
11.89±0.20(Predicted) | [color ]
Light Brown | [InChI]
InChI=1S/C8H6BrNO2/c9-5-1-2-7-6(3-5)10-8(11)4-12-7/h1-3H,4H2,(H,10,11) | [InChIKey]
UQCFMEFQBSYDHY-UHFFFAOYSA-N | [SMILES]
O1C2=CC=C(Br)C=C2NC(=O)C1 |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
22-36/37/38 | [Safety Statements ]
26-36 | [WGK Germany ]
2
| [HS Code ]
2934999090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Uses]
Building block used in the construction of pyrimidinyl substituted benzoxazinones, small molecule rennin inhibitors. | [Synthesis]
General procedure for the synthesis of 6-bromo-2H-1,4-benzoxazin-3(4H)-one from 2-amino-4-bromophenol and chloroacetyl chloride: triethylamine (TEA, 4.06 g, 40 mmol) was added to a tetrahydrofuran (THF, 150 mL) solution of 2-amino-4-bromophenol (5 g, 27 mmol). Subsequently, chloroacetyl chloride (3.33 g, 30 mmol) was added in batches at 0 °C. After 20 min of reaction, the mixture was continued to be stirred for 2 h at room temperature. The reaction mixture was again cooled to 0 °C and sodium hydride (NaH, 60% dispersed in mineral oil, 2.2 g, 54 mmol) was added in batches. After stirring at 0 °C for 20 min, the reaction mixture was brought to room temperature and stirring was continued for 2 h. The reaction mixture was then quenched with water. After completion of the reaction, the reaction was quenched with water. The solvent was removed by distillation under reduced pressure and the resulting residue was diluted with water. The precipitate was collected by filtration, washed with water and dried under vacuum to afford 6-bromo-2H-1,4-benzoxazin-3(4H)-one (5.5 g, 89% yield). | [References]
[1] Journal of Medicinal Chemistry, 2015, vol. 58, # 1, p. 333 - 346
[2] Archiv der Pharmazie, 2018, vol. 351, # 5,
[3] Patent: WO2015/153683, 2015, A1. Location in patent: Paragraph 0936
[4] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 3, p. 1288 - 1296
[5] Patent: WO2008/44022, 2008, A1. Location in patent: Page/Page column 26-27 |
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