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

General Description

6-bromo-2-phenyl-4H-3,1-benzoxazin-4-one is a chemical compound with the molecular formula C13H8BrNO2. It is a benzoxazinone derivative and has a bromine atom attached to the sixth position of the benzene ring. 6-bromo-2-phenyl-4H-3,1-benzoxazin-4-one has potential applications in pharmaceutical and medicinal chemistry due to its structural features, which may allow for the development of new drugs or pharmacologically active molecules. It is also of interest to researchers in the field of organic synthesis due to its unique structure and reactivity. Additionally, the presence of the bromine atom in the molecule may allow for its use in various types of chemical transformations and reactions.

Upstream product

• 495-18-1 Benzohydroxamic acid 
• 19226-36-9 3-phenyl-5H-1,4,2-dioxazol-5-one 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 66416-72-6 4-bromo-2-iodoaniline 
• 98-88-4 benzoyl chloride 
• 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 
• 5794-88-7 5-Bromo-2-aminobenzoic acid 
• 35082-17-8 1-(4-bromophenyl)-2-(1-phenylethylidene)hydrazine 
• 98-86-2 acetophenone 

Downstream Products

• 115754-65-9 6-bromo-2-phenyl-3-amino-4(3H)-quinazolinone 
• 1256947-81-5 C₂₁H₁₅BrN₄O₂ 
• 1256947-94-0 C₂₁H₁₃BrN₄O 
• 1323873-31-9 6-bromo-3-(4-methanesulfonyl-phenyl)-2-phenyl-3H-quinazolin-4-one 
• 1323873-17-1 6-bromo-3-(4-methylsulfanyl-phenyl)-2-phenyl-3H-quinazolin-4-one 
• 857589-28-7 2-benzamido-5-bromobenzoic acid 
• 879556-38-4 6-bromo-3-(6-methoxy-benzothiazol-2-yl)-2-phenyl-3H-quinazolin-4-one 

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.

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.

Recyclable Heterogeneous Palladium-Catalyzed Carbonylative Cyclization of 2-Iodoanilines with Aryl Iodides Leading to 2-Arylbenzoxazinones

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.