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Sigma-Aldrich

2H-1,4-Benzoxazin-3(4H)-one

99%

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About This Item

Empirical Formula (Hill Notation):
C8H7NO2
CAS Number:
5466-88-6
Molecular Weight:
149.15
MDL number:
MFCD00158536
UNSPSC Code:
12352100
PubChem Substance ID:
24863974
NACRES:
NA.22

assay

99%

mp

173-175 °C (lit.)

solubility

methanol: soluble 25 mg/mL, clear, colorless

SMILES string

O=C1COc2ccccc2N1

InChI

1S/C8H7NO2/c10-8-5-11-7-4-2-1-3-6(7)9-8/h1-4H,5H2,(H,9,10)

InChI key

QRCGFTXRXYMJOS-UHFFFAOYSA-N

Related Categories

General description

2H-1,4-Benzoxazin-3(4H)-one, a benzoxazine derivative, is a heterocyclic building block for various natural and synthetic organic compounds. It has been reported as an intermediate during the biogenesis of cyclic hydoxamic acids in maize. Its standard molar enthalpy of formation and tautomerization energy of its tautomers has been evaluated by calorimetric and computational methods. It has been synthesized by reacting o-aminophenol with chloroacetyl chloride in the presence of butanone and aqueous NaHCO3.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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A general and convenient synthesis of 2H-1,4-benzoxazin-3(4H)-ones.
Shridhar DR, et al.
Organic Prep. and Proc. Int., 14(3), 195-197 (1982)
2H-1,4-benzoxazin-3(4H)-one, an intermediate in the biosynthesis of cyclic hydroxamic acids in maize.
Kumar P, et al.
Phytochemistry, 36(4), 893-898 (1994)
Calorimetric and computational study of 2H-1,4-benzoxazin-3(4H)-one and of related species.
Matos MAR, et al.
Molecular Physics, 104(12), 1833-1841 (2006)
Moreshwar B Chaudhari et al.
The Journal of organic chemistry, 85(5), 3374-3382 (2020-01-31)
We report here the Sn-catalyzed mild protocol for ring expansion of peroxyoxindoles to afford the series of substituted-2H-benzo[b][1,4]oxazin-3(4H)-one derivatives. In this protocol, we showed the in situ conversion of tert-butyl peroxy compounds into peresters with the aid of external esters
Jiu Hong Wu et al.
Bioorganic & medicinal chemistry letters, 13(13), 2223-2225 (2003-06-12)
A new inhibitor of in vitro tumor cell replication, cappamensin A (1) (2H-1,4-benzoxazin-3(4H)-one, 6-methoxy-2-methyl-4-carbaldehyde), was isolated from the roots of Capparis sikkimensis subsp. formosana using bioactivity-guided fractionation. The structure of 1 was established by spectroscopic methods, including 2D NMR analyses.
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