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

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

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

• 5794-88-7 5-Bromo-2-aminobenzoic acid 
• 1663-61-2 triethoxymethylbenzene 
• 201230-82-2 carbon monoxide 
• 66416-72-6 4-bromo-2-iodoaniline 
• 98-88-4 benzoyl chloride 
• 495-18-1 Benzohydroxamic acid 
• 19226-36-9 3-phenyl-5H-1,4,2-dioxazol-5-one 
• 591-50-4 iodobenzene 
• 118-92-3 anthranilic acid 
• 189635-01-6 N-(4-bromo-2-cyanophenyl)benzamide 
• 878133-05-2 N-(4-bromo-2-iodophenyl)-2,2,2-trifluoroacetamide 
• 536-74-3 phenylacetylene 
• 1385659-98-2 N-(4-bromo-2-(phenylethynyl)phenyl)-2,2,2-trifluoroacetamide 
• 35082-17-8 1-(4-bromophenyl)-2-(1-phenylethylidene)hydrazine 

Downstream Products

• 87602-33-3 3-(5-Allylsulfanyl-[1,3,4]thiadiazol-2-yl)-6-bromo-2-phenyl-3H-quinazolin-4-one 
• 87602-36-6 6-Bromo-3-(5-oxiranylmethylsulfanyl-[1,3,4]thiadiazol-2-yl)-2-phenyl-3H-quinazolin-4-one 
• 87602-39-9 [5-(6-Bromo-4-oxo-2-phenyl-4H-quinazolin-3-yl)-[1,3,4]thiadiazol-2-ylsulfanyl]-acetic acid 
• 639482-27-2 2-benzamido-5-bromobenzamide 
• 1286247-84-4 6-bromo-2-phenyl-3-(2'-morpholinophenyl)quinazolin-4(3H)-one 
• 1256947-81-5 C₂₁H₁₅BrN₄O₂ 
• 1256947-94-0 C₂₁H₁₃BrN₄O 
• 1223089-96-0 6-bromo-2-phenyl-3-{4-[(E)-3-(4-methoxyphenyl)-acryloyl]phenyl}-3H-quinazolin-4-one 
• 1223090-03-6 6-bromo-2-phenyl-3-{4-[(E)-3-(naphthalene-2-yl)-acryloyl]phenyl}-3H-quinazolin-4-one 
• 1223090-09-2 6-bromo-2-phenyl-3-[4-(5-(p-anisyl)-4,5-dihydro-1-acetyl-1H-pyrazol-3-yl)-phenyl]-3H-quinazolin-4-one 
• 1223089-77-7 6-[4-(6-bromo-2-phenyl-4-oxo-4H-quinazolin-3-yl)-phenyl]-2-oxo-4-(furan-2-yl)-1,2-dihydropyridine-3-carbonitrile 
• 1223089-85-7 6-{4-[6-bromo-2-phenyl-4-oxo-4H-quinazolin-3-yl]-phenyl}-2-imino-4-(2-hydroxyphenyl)-1,2-dihydropyridine-3-carbonitrile 
• 1223089-92-6 6-{4-[6-bromo-2-phenyl-4-oxo-4H-quinazolin-3-yl]-phenyl}-2-amino-4-(p-tolyl)-4,4-dihydropyran-3-carbonitrile 
• 857589-28-7 2-benzamido-5-bromobenzoic 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.

From Methaqualone and Beyond: Structure - Activity Relationship of 6-, 7-, and 8-Substituted 2,3-Diphenyl-quinazolin-4(3H)-ones and in Silico Prediction of Putative Binding Modes of Quinazolin-4(3H)-ones as Positive Allosteric Modulators of GABAA

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A highly efficient and practical heterogeneous palladium-catalyzed carbonylative coupling of 2-iodoanilines with aryl iodides has been developed. The reaction occurs smoothly in toluene at 110 °C with N, N -diisopropylethylamine as base under carbon monoxide (5 bar) and offers a general and powerful tool for the construction of various valuable 2-arylbenzoxazinones with excellent atom-economy, high functional group tolerance, good to high yields, and easy recyclability of the palladium catalyst. The reaction is the first example of heterogeneous palladium-catalyzed carbonylative coupling for the preparation of diverse 2-arylbenzoxazinones from commercially easily available 2-iodoanilines and aryl iodides.

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.

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