7-Bromo-2H-benzo[b][1,4]oxazin-3(4H)-one Chemical Properties

Boiling point:

381.5±42.0 °C(Predicted)

Density 

1.676

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

11.76±0.20(Predicted)

Appearance

Light brown to brown Solid

InChI

InChI=1S/C8H6BrNO2/c9-5-1-2-6-7(3-5)12-4-8(11)10-6/h1-3H,4H2,(H,10,11)

InChIKey

ZAXUQDMKVBOVCR-UHFFFAOYSA-N

SMILES

O1C2=CC(Br)=CC=C2NC(=O)C1

Safety Information

HS Code 

2934999090

7-Bromo-2H-benzo[b][1,4]oxazin-3(4H)-one Usage And Synthesis

Uses

7-Bromo-2H-benzo[b][1,4]oxazin-3(4H)-one is used in the pharmaceutical field as an anticancer agent component, and in organic synthesis as a synthetic reaction reagent or intermediate component.

Synthesis

2. 2-Amino-5-bromophenol (2.53 g, 18.2 mmol, 1.0 eq.) was dissolved in a solvent mixture of 15 mL of isobutylmethyl ketone and 15 mL of water, and cooled to 0 °C. Subsequently, NaHCO3 (3.67 g, 2.4 eq.) and chloroacetyl chloride (2.36 g, 1.67 mL, 1.15 eq.) were added. The reaction mixture was heated to reflux and stirred overnight, then cooled to room temperature. After completion of the reaction, the mixture was diluted with ethyl acetate, washed sequentially with water, dried with MgSO4 and finally concentrated under vacuum. Purification by silica gel column chromatography afforded 7-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-one in 77% yield. After analyzed by low resolution mass spectrometry (LRMS), the molecular ion peak (M + H)+ was measured to be 180.1, which was consistent with the theoretical value of C9H10NO3.

References

[1] Journal of Medicinal Chemistry, 2015, vol. 58, # 1, p. 222 - 236
[2] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 5, p. 592 - 597
[3] MedChemComm, 2015, vol. 6, # 7, p. 1375 - 1380
[4] ChemMedChem, 2015, vol. 10, # 11, p. 1821 - 1836
[5] Patent: US6534535, 2003, B1

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• BUTTPARK 120\07-73