2-(2-Hydroxyphenyl)-4H-benzo[e][1,3]oxazin-4-one

Name: 2-(2-Hydroxyphenyl)-4H-benzo[e][1,3]oxazin-4-one
Brand: ChemScene
Availability: InStock
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CAS No. 1218-69-5
Cat. No. CS-0315238
Purity≥95%
MDL No.MFCD02234511

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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2-(2-Hydroxyphenyl)-4H-benzo[e][1,3]oxazin-4-one|CS-0315238

Structure of 1218-69-5

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General Information

CAS No. 1218-69-5
Cat. No. CS-0315238
Purity ≥95%
MDL No. MFCD02234511
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₉NO₃
Molecular Weight 239.23
Synonym(s) 4H-1,3-Benzoxazin-4-one, 2-(2-hydroxyphenyl)-
SMILES C1=CC=C(C(=C1)C2=NC(=O)C3=CC=CC=C3O2)O

Description

This oxazinone scaffold features a hydroxyl group positioned ortho to the phenyl ring, enabling intramolecular hydrogen bonding that enhances stability and modulates reactivity. The fused heterocyclic system imparts electron-deficient character at the carbonyl-bearing carbon, facilitating nucleophilic attack in synthetic transformations. This structural motif serves as a key intermediate in the synthesis of bioactive compounds and functional materials, particularly those requiring rigid, planar architectures with defined polarity.

Application

2-(2-Hydroxyphenyl)-4H-benzo[e][1,3]oxazin-4-one serves as a versatile heterocyclic building block for medicinal chemistry and materials science applications. Its fused oxazinone core exhibits enhanced stability and favorable solubility, enabling efficient derivatization via electrophilic substitution or transition-metal-catalyzed coupling. The phenolic hydroxyl group facilitates direct functionalization or metal chelation, while the lactam carbonyl supports orthogonal reactivity—making this scaffold valuable in the synthesis of bioactive compounds and functional polymers.

Synthesis

Route1
- 1972-71-0
- ~92%
- In-stock
  
  1218-69-5
References
- FUJIFILM Corporation Patent: EP2460799 A1, 2012 ; Location in patent: Page/Page column 40-41 ;
Route2
- 65-45-2
- 69-72-7
- ~56%
- In-stock
  
  1218-69-5
References
- Steinhauser, Stefan; Heinz, Uwe; Bartholomae, Mark; Weyliermueller, Thomas; Nick, Hanspeter; Hegetschweiler, Kaspar European Journal of Inorganic Chemistry, 2004 , # 21 p. 4177 - 4192
Route3
- 65-45-2
- 1441-87-8
- ~64%
- In-stock
  
  1218-69-5
References
- ERREGIERRE S.P.A.; FERRARI, Massimo; GALLI, Matteo Patent: WO2012/131017 A1, 2012 ; Location in patent: Page/Page column 7 ;

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 63.33
LogP 2.5606
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Other aromatic heterocycles compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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2-(2-Hydroxyphenyl)-4H-benzo[e][1,3]oxazin-4-one

CAS No. 1218-69-5

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