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HomeProduct name list2-Methyl-4H-3,1-benzoxazin-4-one

2-Methyl-4H-3,1-benzoxazin-4-one

  • CAS NO.:525-76-8
  • Empirical Formula: C9H7NO2
  • Molecular Weight: 161.16
  • MDL number: MFCD00047647
  • EINECS: 208-381-7
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-07-05 11:27:04
2-Methyl-4H-3,1-benzoxazin-4-one Structural

What is 2-Methyl-4H-3,1-benzoxazin-4-one?

The Uses of 2-Methyl-4H-3,1-benzoxazin-4-one

2-Methyl-4H-3,1-benzoxazin-4-one is a synthetic antimicrobial agent. It belongs to the quinazolinone class of drugs. It has been shown to be effective against Staphylococcus aureus and other bacteria. Quinazolinones are potent inhibitors of bacterial growth and have been used successfully in the treatment of tuberculosis and other infectious diseases. 2-Methyl-4H-3,1-benzoxazin-4-one has also been shown to inhibit the growth of some Gram-negative bacteria, such as Salmonella typhi and Escherichia coli.

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 363, 1980 DOI: 10.1021/jo01290a038

Synthesis

In 250 mL of RBF took (0.01 mole or 1.37 gm) anthranilic acid (2-amino benzoic acid) to that added 15 mL of acetic anhydride (excess) with porcelain chips. Reflux the solution at 35-40 ℃ for 50-55 min on heating mantle. TLC was done using EA: n-hexane (1:1) solvent system. Then removed the excess solvent (acetic anhydride) at low pressure using rotatory evaporator, To the remaining solid, added petroleum ether (40-60) to extract the 2-methyl-4H-3,1-benzoxazin-4-one. Repeated petroleum ether step to extract the entire product. After drying of petroleum-ether, the crystals of 2-methyl-4H-3, 1-benzoxazin-4-one was obtained and then it was recrystallized with ethanol8. M.P 80-82℃, Yield 79 %.
2-METHYL-3,1-BENZOXAZA-4-ONE

Properties of 2-Methyl-4H-3,1-benzoxazin-4-one

Melting point: 79-82 °C(lit.)
Boiling point: 144-145 °C(Press: 12 Torr)
Density  1.25±0.1 g/cm3(Predicted)
storage temp.  under inert gas (nitrogen or Argon) at 2-8°C
pka 2.84±0.20(Predicted)
InChI InChI=1S/C9H7NO2/c1-6-10-8-5-3-2-4-7(8)9(11)12-6/h2-5H,1H3
EPA Substance Registry System 4H-3,1-Benzoxazin-4-one, 2-methyl- (525-76-8)

Safety information for 2-Methyl-4H-3,1-benzoxazin-4-one

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for 2-Methyl-4H-3,1-benzoxazin-4-one

InChIKey WMQSKECCMQRJRX-UHFFFAOYSA-N
SMILES N1C2=CC=CC=C2C(=O)OC=1C

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