66387-70-0

Basic information

• Product Name: 6-bromo-2-phenyl-4H-3,1-benzoxazin-4-one
• Synonyms: 6-Bromo-2-phenyl-benzo[d][1,3]oxazin-4-one
• CAS NO: 66387-70-0
• Molecular Formula: C₁₄H₈BrNO₂
• Molecular Weight: 302.1228
• Mol File: 66387-70-0.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 405.9°C at 760 mmHg
• Flash Point: 199.3°C
• Density: 1.56g/cm³
• Vapor Pressure: 8.48E-07mmHg at 25°C
• Refractive Index: 1.669
• CAS DataBase Reference: 6-bromo-2-phenyl-4H-3,1-benzoxazin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-bromo-2-phenyl-4H-3,1-benzoxazin-4-one(66387-70-0)
• EPA Substance Registry System: 6-bromo-2-phenyl-4H-3,1-benzoxazin-4-one(66387-70-0)

Safety Data

• Hazardous Substances Data: 66387-70-0(Hazardous Substances Data)

Usage

Description

6-bromo-2-phenyl-4H-3,1-benzoxazin-4-one is a benzoxazinone derivative with the molecular formula C13H8BrNO2. It features a bromine atom attached to the sixth position of the benzene ring, which contributes to its unique structure and reactivity. This chemical compound holds potential in pharmaceutical and medicinal chemistry for the development of new drugs or pharmacologically active molecules, and is also of interest to researchers in organic synthesis.

Uses

Used in Pharmaceutical and Medicinal Chemistry:
6-bromo-2-phenyl-4H-3,1-benzoxazin-4-one is used as a chemical intermediate for the development of new drugs or pharmacologically active molecules, leveraging its structural features and reactivity.
Used in Organic Synthesis:
In the field of organic synthesis, 6-bromo-2-phenyl-4H-3,1-benzoxazin-4-one is used as a key compound for exploring its unique structure and reactivity, which may lead to the discovery of novel chemical transformations and reactions.

Upstream product

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Downstream Products

• 1256947-81-5 C₂₁H₁₅BrN₄O₂ 
• 1256947-94-0 C₂₁H₁₃BrN₄O 
• 87602-30-0 6-Bromo-2-phenyl-3-(5-mercapto-1,3,4-thiadiazol-2-yl)-quinazolin-4(3H)-one 
• 87888-63-9 4-(6-Bromo-4-oxo-2-phenyl-4H-quinazolin-3-yl)-2-hydroxy-benzoic acid 
• 84325-80-4 6-Bromo-3-(4-hydroxyphenyl)-2-phenyl-quinazolin-4(3H)-one 
• 77995-29-0 [4-(6-Bromo-4-oxo-2-phenyl-4H-quinazolin-3-yl)-phenylsulfanyl]-acetic acid 

Relevant articles and documents

Direct synthesis of benzoxazinones via Cp*Co(III)-catalyzed C–H activation and annulation of sulfoxonium ylides with dioxazolones

A highly novel and direct synthesis of benzoxazinones was developed via Cp*Co(III)-catalyzed C–H activation and [3 + 3] annulation between sulfoxonium ylides and dioxazolones. The reaction is conducted under base-free conditions and tolerates various functional groups. Starting from diverse readily available sulfoxonium ylides and dioxazolones, a variety of benzoxazinones could be synthesized in one step in 32%-75% yields.

Recyclable Heterogeneous Palladium-Catalyzed Cyclocarbonylation of 2-Iodoanilines with Acyl Chlorides in the Biomass-Derived Solvent 2-Methyltetrahydrofuran

A highly efficient, green palladium-catalyzed cyclocarbonylation of 2-iodoanilines with acyl chlorides has been developed that proceeds smoothly in a biomass-derived solvent 2-methyltetrahydrofuran with N,N-diisopropylethylamine as base at 100 °C under 20 bar of carbon monoxide using an 2-aminoethylamino-modified MCM-41-anchored palladium acetate complex [2N-MCM-41-Pd(OAc)2] as a heterogeneous catalyst, yielding a wide variety of 2-substituted 4H-3,1-benzoxazin-4-one derivatives in good to excellent yields. This supported palladium catalyst could be facilely obtained by a two-step procedure from easily available starting materials and readily recovered via a simple filtration process and recycled at least 8 times without any apparent decrease in catalytic efficiency. The developed methodology not only avoids the use of toxic solvents such as tetrahydrofuran and dimethylformamide but also solves the basic problem of expensive palladium catalyst recovery and reuse and prevents effectively palladium contamination of the desired product.

Design, synthesis and anticancer activity of novel triazole substituted quinazoline hybrids

Quinazolines and 1,2,4-triazoles are important class of nitrogen containing heterocyclic compounds having immense biological importance. From the literature review, pharmacokinetic properties of a drug can be modified or enhanced by building a triazole moiety into a compound like quinazoline. Therefore, the study of new hybrid systems which combines triazole system with quinazoline is still seemed warranted. In the present study, a sequence of novel 1,2,4-triazole derivatives containing quinazolinyl moiety were designed, synthesized and screened for their in vitro anticancer activity. Thirteen new hybrids are synthesized from readily accessible 5-bromoanthranilic acid. All the hybrid compounds were well explicated by IR,1H,13C NMR, and mass spectral data. Out of 13, some of the compounds manifested moderate to good antiproliferative activity against two cancer cell lines (HepG2 and MCF-7). Remarkably, compounds 8A, 16H and 16K displayed potent activity (14-49 μM) on both HepG2 (liver carcinoma) and MCF-7 (breast cancer) cell lines whereas compounds 8B, 8F, 16L, and 15 displayed substantial activity against HepG2 cancer cell line (34-65 μM). Synthetic approach described here is very simple and can be used for the syntheses of related compounds library which is useful for the exploration of further biological activities and is currently underway in our laboratory.