3597-63-5

Basic information

• Product Name: 3-HYDROXY-2H-1,4-BENZOXAZINE-2-ONE
• Synonyms: 3-HYDROXY-2H-1,4-BENZOXAZINE-2-ONE;2H-1,4-benzoxazine-2,3(4H)-dione;Einecs 222-744-7;3-Hydroxy-2H-benzo[b][1,4]oxazin-2-one;4H-1,4-benzoxazine-2,3-dione;4H-1,4-benzoxazine-2,3-quinone
• CAS NO: 3597-63-5
• Molecular Formula: C₈H₅NO₃
• Molecular Weight: 163.13
• EINECS: 222-744-7
• Mol File: 3597-63-5.mol
• Article Data: 10

Chemical Properties

• Melting Point: 258-259 °C(Solv: ethanol (64-17-5))
• Appearance: /
• Density: 1.402 g/cm³
• Refractive Index: 1.585
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.10±0.20(Predicted)
• CAS DataBase Reference: 3-HYDROXY-2H-1,4-BENZOXAZINE-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXY-2H-1,4-BENZOXAZINE-2-ONE(3597-63-5)
• EPA Substance Registry System: 3-HYDROXY-2H-1,4-BENZOXAZINE-2-ONE(3597-63-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 3597-63-5(Hazardous Substances Data)

Usage

Description

3-Hydroxy-2H-1,4-benzoxazine-2-one is a heterocyclic organic compound with the molecular formula C7H5NO3, featuring a benzoxazine ring. It is recognized for its potential applications in the synthesis of thermosetting resins, as well as its biological activities, such as anti-cancer and anti-inflammatory properties. Furthermore, it has been explored for its use as a corrosion inhibitor in various industries.

Uses

Used in Adhesives and Composites Industry:
3-Hydroxy-2H-1,4-benzoxazine-2-one is used as a monomer for synthesizing thermosetting resins, which are crucial in the production of high-performance adhesives and composite materials. These resins offer excellent thermal stability, mechanical strength, and chemical resistance, making them suitable for various applications in this industry.
Used in Coatings Industry:
In the coatings industry, 3-Hydroxy-2H-1,4-benzoxazine-2-one serves as a monomer in the creation of thermosetting resins that contribute to the development of durable and heat-resistant coatings. These coatings are vital for protecting surfaces in automotive, aerospace, and other industries that demand high-performance materials.
Used in Pharmaceutical Research:
3-Hydroxy-2H-1,4-benzoxazine-2-one is being studied for its potential biological activities, such as its anti-cancer properties. It may be utilized as a compound in the development of new pharmaceuticals targeting cancer treatment, offering a novel approach to managing and treating various types of cancer.
Used in Anti-Inflammatory Research:
3-HYDROXY-2H-1,4-BENZOXAZINE-2-ONE is also being investigated for its anti-inflammatory properties, which could lead to its use in the development of new medications for treating inflammation-related conditions. This application could provide an alternative or complementary treatment option for various inflammatory diseases.
Used in Corrosion Inhibition:
3-Hydroxy-2H-1,4-benzoxazine-2-one has been explored for its potential as a corrosion inhibitor in industrial applications. It can be used to protect metals and materials from corrosion, extending their service life and reducing maintenance costs in various industries, such as oil and gas, automotive, and construction.

InChI:InChI=1/C8H5NO3/c10-7-8(11)12-6-4-2-1-3-5(6)9-7/h1-4H,(H,9,10)

Upstream product

• 824-38-4 potassium 2-nitrophenoxide 
• 95-55-6 2-amino-phenol 
• 95-92-1 oxalic acid diethyl ester 
• 91-56-5 indole-2,3-dione 
• 79-37-8 oxalyl dichloride 
• 142071-82-7 3-benzoylpyrrolo[2,1-c][1,4]benzoxazine-1,2,4-trione 
• 17318-84-2 Ethyl o-Nitrophenyl Oxalate 
• 27383-59-1 ethyl (2-hydroxyphenylcarbamoyl)formate 

Downstream Products

• 27383-81-9 3-chloro-1,4-benzoxazin-2-one 
• 90292-16-3 4-{[Bis-(2-hydroxy-ethyl)-amino]-methyl}-2-[(E)-3-trifluoromethyl-phenylimino]-4H-benzo[1,4]oxazin-3-one 
• 90292-14-1 Acetic acid [3-oxo-4-(4-phenyl-piperazin-1-ylmethyl)-3,4-dihydro-benzo[1,4]oxazin-(2E)-ylidene]-hydrazide 
• 90292-18-5 4-Piperidin-1-ylmethyl-2-[(E)-3-trifluoromethyl-phenylimino]-4H-benzo[1,4]oxazin-3-one 
• 90292-17-4 4-Morpholin-4-ylmethyl-2-[(E)-3-trifluoromethyl-phenylimino]-4H-benzo[1,4]oxazin-3-one 
• 90292-20-9 4-{[Bis-(2-hydroxy-ethyl)-amino]-methyl}-2-[(E)-2-methoxy-4-nitro-phenylimino]-4H-benzo[1,4]oxazin-3-one 
• 27383-90-0 benzooxazole-2-carboxylic acid 4-chloro-phenyl ester 
• 27411-62-7 benzooxazole-2-carboxylic acid phenethylamide 
• 27384-00-5 benzooxazole-2-carbothioic acid S-benzyl ester 
• 27383-89-7 phenyl benzo[d]oxazole-2-carboxylate 
• 27411-89-8 3-(3,5-bis-trifluoromethyl-anilino)-benzo[1,4]oxazin-2-one 
• 27411-86-5 3-(3,5-dichloro-anilino)-benzo[1,4]oxazin-2-one 
• 27625-86-1 blepharin 
• 23520-34-5 Blepharigenin 

Relevant articles and documents

Cleavage of Pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones with Thiocarbonohydrazide. Synthesis of Substituted 4-Amino-1,2,4-triazines

3-Acylpyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones reacted with thiocarbonohydrazide to give mixtures of 4-amino-6-(acylmethyl)-3-sulfanylidene-3,4-dihydro-1,2,4-triazin-5(2H)-ones and 6-substituted 1,4-benzoxazine-2,3-diones which can be separated by fractional crystallization directly from the reaction mixture. The reaction is likely to involve a sequence of nucleophilic transformations with intermediate formation of spiro[pyrrole-2,6′-[1,2,4]triazines] which undergo cleavage of the C2-N1 bond in the pyrrole ring. The structure of the products was determined by X-ray analysis, and intermediate products were identified by UPLC/MS. 1,2,4-Triazine derivatives can also be synthesized independently from alkyl 2,4-dioxobutanoates or 2-oxobutanedioic acid and thiocarbonohydrazide. The known procedure for the synthesis of 4-amino-1,2,4-triazines from 4-aryl-2,4-dioxobutanoic acids and thiocarbonohydrazide was improved to meet the “green chemistry” principles. Two new methods for the synthesis of substituted 4-amino-1,2,4-triazines were developed. The obtained compounds attract interest for medicinal chemistry, pharmacology, and fine organic synthesis.

Rationalization of benzazole-2-carboxylate versus benzazine-3-one/ benzazine-2,3-dione selectivity switch during cyclocondensation of 2-aminothiophenols/phenols/anilines with 1,2-biselectrophiles in aqueous medium

The cyclocondensation reaction of 2-aminothiophenols with 1,2-biselectrophiles such as ethyl glyoxalate and diethyl oxalate in aqueous medium leads to the formation of benzothiazole-2-carboxylates via the 5-endo-trig process contrary to Baldwin's rule. On the other hand, the reaction of 2-aminophenols/anilines produced the corresponding benzazine-3-ones or benzazine-2,3-diones via the 6-exo-trig process in compliance with Baldwin's rule. The mechanistic insights of these cyclocondensation reactions using the hard-soft acid-base principle, quantum chemical calculations (density functional theory), and orbital interaction studies rationalize the selectivity switch of benzothiazole-2-carboxylates versus benzazine-3-ones/ benzazine-2,3-diones. The presence of water facilitates these cyclocondensation reactions by lowering of the energy barrier.

Synthesis of new [1,2,3]triazoles and 1H-tetrazoles via reactions of 3,(5)-(Di)chloro-2H-1,4-(benz)oxazin-2-ones with diazocompounds or sodium azide

Treatment of 3,(5)-(di)chloro-2H-1,4-(benz)oxazin-2-ones with diazo compounds or sodium azide yields bi(tri)cyclic compounds which can be converted into [1,2,3]triazoles or 1,5-disubstituted tetrazoles via reactions with nucleophiles as methanol, water and amines.