31499-90-8

Basic information

• Product Name: 2,1-Benzisoxazol-3(1H)-one
• Synonyms: 2,1-Benzisoxazol-3(1H)-one
• CAS NO: 31499-90-8
• Molecular Formula: C₇H₅NO₂
• Molecular Weight: 135.1201
• Mol File: 31499-90-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 112 °C
• Boiling Point: 240.8°Cat760mmHg
• Flash Point: 99.4°C
• Appearance: /
• Density: 1.323g/cm³
• Vapor Pressure: 0.0372mmHg at 25°C
• Refractive Index: 1.586
• PKA: -1.46±0.20(Predicted)
• CAS DataBase Reference: 2,1-Benzisoxazol-3(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,1-Benzisoxazol-3(1H)-one(31499-90-8)
• EPA Substance Registry System: 2,1-Benzisoxazol-3(1H)-one(31499-90-8)

Safety Data

• Hazardous Substances Data: 31499-90-8(Hazardous Substances Data)

Usage

Synthesis

The mixture of 13.1 mg (0.078 mmol) of 2-azidobenzoic acid and 10.8 mg (0.078 mmol) of potassium carbonate in 10 mL ethanol was irradiated for 1 h with intensive stirring. The reaction mixture was added to 50 mL water, extracted with benzene and eluted through silica gel. The benzisoxazole-containing solution was evaporated in vacuo affording 2,1-benzisoxazole-3(1H)-one with 75% yield. Pale yellow crystals reddening at room temperature and stored at ?20 °C. 1H NMR (400 MHz, CDCl3) δ 8.69 (s, 1H), 7.85 (d, J = 7.8 Hz, 1H), 7.68 (t, J = 7.7 Hz, 1H), 7.31 (s, 1H), 7.23 (d, J = 8.2 Hz, 1H). 13C NMR (101 MHz, CDCl3) δ 169.0, 155.6, 135.2, 125.8, 124.7, 112.6, 111.9; IR (suspension in nujol oil, cm-1 ): 3127 (ν NH); 1744, 1719 (ν C=O); 1068 (ν CO); m/z (rel, intensity) 136.02(M+ +2, 5.64), 134.91(M+ , 100.00), 118.93(2.73), 103.94(3.61), 90.92(M+-CO2, 14.07), 78.94(7.04), 76.97(5.45), 75.94(8.75), 63.98(10.01), 62.96(6.98), 51.99(11.24), 50.97(3.55), 49.95(4.86), 43.99(8.23), 39.95(2.83).

Synthesis Reference(s)

Journal of Medicinal Chemistry, 27, p. 1212, 1984 DOI: 10.1021/jm00375a022

InChI:InChI=1/C7H5NO2/c9-7-5-3-1-2-4-6(5)8-10-7/h1-4,8H

Upstream product

• 5385-87-5 o-nitrobenzyl diazomethane 
• 140472-35-1 N-(o-nitrobenzoyl)-acetamide 
• 31162-13-7 2-azidobenzoic acid 

Downstream Products

• 216446-38-7 2-(3-oxo-1,3-dihydro-2,1-benzisoxazol-1-ylmethyl)benzonitrile 
• 253668-53-0 1-(2-chloromethylbenzoyl)-2,1-benzisoxazol-3(1H)-one 
• 51310-21-5 3-(2-carbomethoxyphenyl)-4(3H)-quinazolinone 
• 1898-06-2 3-amino-2-methyl-4-oxoquinazoline 
• 14663-46-8 3-amino-3,4-dihydroquinazolin-4-one 
• 118-92-3 anthranilic acid 
• 54175-73-4 2-(benzo[d]oxazol-2-yl)benzonitrile 
• 525-76-8 2-methyl-4-oxo-3,1-benzoxazine 
• 95-21-6 2-methyl-1,3-benzoxazole 
• 776-41-0 indole-3-carboxylic acid ethyl ester 
• 573-79-5 2,2'-azoxy-di-benzoic acid 
• 635-54-1 2,2'-azobenzoic acid 
• 3342-77-6 N-formylanthranilic acid 
• 123534-30-5 1-(4'-methylphenylsulfonyl)-2,1-benzisoxazol-3(1H)-one 

Relevant articles and documents

One-Step Synthesis of 2-[(2-Carboxyphenyl)amino]-6-formylnicotinic Acid via Photolysis of 2-Azidobenzoic Acid in the Presence of Weak Bases

Abstract: 2-Azidobenzoic acid has undergone rearrangement into 2-[(2-carboxyphenyl)amino]-6-formylnicotinic acid under irradiation in aqueous-organic media in the presence of acetates of alkali or alkaline earth metals. The structure of the resulting comp

Synthesis of 2,1-benzisoxazole-3(1H)-ones by base-mediated photochemical N-O bond-forming cyclization of 2-azidobenzoic acids

The base-mediated photochemical cyclization of 2-azidobenzoic acids with the formation of 2,1-benzisoxazole-3(1H)-ones is reported. The optimization and scope of this cyclization reaction is discussed. It is shown that an essential step of the ring closure of 2-azidobenzoic acids is the formation and photolysis of 2-azidobenzoate anions.

Photochemistry of (2-nitrophenyl)diazomethane studied by the matrix isolation technique. (Nitrophenyl)carbene to (carboxylphenyl)nitrene rearrangement by successive reduction of the nitro group with the carbenic center

Irradiation (λ > 350 nm) of (2-nitrophenyl)diazomethane (1) matrix-isolated in Ar at 10 K provided 2-nitrosobenzaldehyde (3) presumably as a result of intramolecular oxygen migration in (2-nitrophenyl)carbene (2). Upon further irradiation (λ > 350 nm), 3 was decomposed to give a mixture of 2,1-benzisoxazol-3(1H)-one (4) and carbonylcyclopentadiene imine (5) along with CO2. The oxazolone (4) underwent decarboxylation to give 5 upon irradiation with shorter wavelength light (λ > 300 nm) but not at longer wavelength (λ > 350 nm), suggesting 4 is not the direct precursor for 5 in the photolysis of 3. Irradiation (λ > 350 nm) of (4-n-butyl-2-nitrophenyl)diazomethane (1b) under similar conditions resulted in the formation of carbonyloximinocyclohexadienylidene (7) which then produced the oxazolone (4b) and the imine (5b) upon further irradiation, suggesting that a 1,4-biradical generated as a result of abstraction of H at the ortho position by the photoexcited nitroso group was involved in the reaction of 3 forming 4. (2-Carboxyphenyl)nitrene (9) generated by 1,4-OH shift in the 1,4-biradical was postulated as an intermediate leading to 5, and this was actually demonstrated by independent generation of 9 by the photolysis of 2-azidobenzoic acid (8).