Category: 271-95-4

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called NMR study of isomeric benzoxazoles, published in 1972, which mentions a compound: 271-95-4, Name is 1,2-Benzisoxazole, Molecular C7H5NO, Recommanded Product: 271-95-4.

NMR spectra of anthranil (I, R = H), 3-methylanthranil (I, R = Me), benzisoxazole (II, R = H), and 3-methylbenzisoxazole (II, R = Me) were compared with computer-simulated spectra. Long-range coupling (including 5J) constants were determined and discussed.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

Safety of 1,2-Benzisoxazole. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 1,2-Benzisoxazole, is researched, Molecular C7H5NO, CAS is 271-95-4, about Stability, degradation impurities and decomposition kinetics for paliperidone from osmotic tablets. Author is Cassol, Jose Pedro Etchepare; de Souza Barbosa, Fabio; Garcia, Cassia V.; Mendez, Andreas S. L..

The antipsychotic paliperidone was investigated with a focus on stability, degradation impurities and kinetics reaction profile. Osmotic tablets 3 mg (OROS) were subjected to extraction in an ultrasonic bath and the resulting acidic solution was stressed by forced conditions. Degraded samples were monitored by HPLC-DAD in different storage times for acidic and alk. hydrolysis, oxidation, heat and photolysis. Photolysis was shown to be a strong degradation factor, with a drug content of 24.64% remaining after 24 h. Oxidation (H2O2 18%) caused a slow decomposition, with a drug content of 83.49% remaining after 72 h. Through kinetics graphics, first-order reactions were found for oxidation, heat and photolysis. By UPLC-MS anal., the degraded matrix could be investigated for identification of impurities with m/z 445.3128, m/z 380.8906, m/z 364.9391, m/z 232.9832 and m/z 217.0076, allowing the identification of derivatives N-oxide and with modifications in the lactam, benzisoxazole and pyrimidine rings. Paliperidone in liquid state, like anal. solutions or formulation, must be carefully handled to avoid drug exposure, specially in storage conditions.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

Fishbein, Lawrence; Falk, Hans L.; Fawkes, John; Jordan, S. published an article about the compound: 1,2-Benzisoxazole( cas:271-95-4,SMILESS:C12=CC=CC=C1ON=C2 ).Formula: C7H5NO. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:271-95-4) through the article.

Hazards which may be encountered on repeated and prolonged inhalation or contact with pesticidal synergists are discussed; included are methylenedioxyphenyl pesticidal synergists, and other classes of synergistic agents. Detoxification and detoxification inhibition are also discussed.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Derivatives of o-Iodo-p-toluidine and of o-Iodo-p-nitrobenzoic Acid with Monoand Polyvalent Iodine》. Authors are Willgerodt, C.; Gartner, Rudolf.The article about the compound:1,2-Benzisoxazolecas:271-95-4,SMILESS:C12=CC=CC=C1ON=C2).Formula: C7H5NO. Through the article, more information about this compound (cas:271-95-4) is conveyed.

o-Iodo-p-toluidine, MeC6H3INH2, from 2-iodo-4-nitro-1-toluene and Fe(OH)2, in presence of aqueous NH3. Long, colorless needles, m. 37°. It is a very feeble base and its salts are decomposed by H2O. Hydrochloride, long, dark needles. Sulphate, lustrous plates. Nitrate, well developed, rhombic crystals, less soluble than the salts described above. Oxalate, small, rhombic crystals, m. and decomposes 103°. Carbamide, well developed, rhombic crystals, m. 194°. Nitrosocarbamide, yellow, lustrous needles, m. and decomposes 99°. It is unstable in air. Acetyl derivative,MeC6H3INHAc, colorless, interlaced needles, m. 130°. In alkaline soluble KMnO4 converts it into o-iodop-acetaminobenzoic acid (see below). With Cl it forms the iodo-dichloride, yellow needles, decomposes about 100°. Phenyl-p-acetaminotolyliodinium hydroxide, MeC6H3 (NHAc)IPhOH, from the preceding compound and HgPh2; alkaline. Iodide, pale yellow needles, m. 145°. It is unstable in air. Bromide, colorless rods, m. 159.5-60°. Bichromate, reddish brown needles, decomposes 80°. Chloroplatinate, small, yellow crystals, decomposes 110°, m. and evolves gas 125°. 2-Iodo-4-nitro-1-toluene, with HNO3 (d. 1.28), at 110-5° yields o-iodo-p-nitrobenzoic acid, O2NC6H3ICO2H; very long, pale yellow needles, m. 142°. Silver salt, colorless needles, unstable in air. Barium salt, crystals with I H2O. Methyl ester, long needles, m. 89°. Ethyl ester, large, highly lustrous rods, m. 44°. Chloride, yellow needles, b18 196°. Amide, yellow, rhombic crystals, m. 205°. o-Iodo-p-nitrobenzophenone, O2NC6H3IBz, from the chloride, AlCl3 and C6H6. Bundles of small needles, m. 90-1°. Oxime, from EtOH and HONH3Cl. Small rods, m. 161-1.5°. Indoxazene, formula (I) below, from the ketone, HONH3Cland alkali. Small, rhombic crystals, m. 139°. p-Nitrobenzoic acid o-iodo dichloride,yellow needles. Iodoso derivative (II) or (III), from the preceding compound and NaOH. Colorless, interlaced needles; various specimens m. 190-201°. It gives yellow solutionswith alkalies and concentrate H2SO4; when heated the latter solution liberates I. In Ac2Oand PhNH2 the color is red; after adding H2O the liquid shows a green fluorescence. The acid is stable towards boiling HCO2H, but Ac2O converts it into the iodo-nitrobenzoic acid. By the action of NaOH it yields NaIO3, and sodium iodonitrobenzoateand p-nitrobenzoate. The following derivatives of the iodoso acid have been prepared.Sodium salt, brown plates. Silver salt, small needles, explodes when heated. Bariumsalt, yellow needles. Copper salt, light green and amorphous. Lead salt, yellow powder. Methyl ester, small, interlaced needles, m. 180-1°. Iododichloride, yellow and crystalline. o-lodoxy-p-nitrobenzoic acid, O2IC6H3(NO2)CO2H, from the iodosoacid and KMnO4 in acid solution, or from NaOCl. Colorless needles, m. and explodesslightly 205°. It decomposes carbonates as also does the iodoso acid, and has a sourtaste. Silver salt, small needles, explodes violently when heated. Lead salt, paleyellow and amorphous. o-Iodo-p-acetaminobenzoic acid, AcNHC6H3ICO2H, from theiodoacettoluidide described above and KMnO4, in presence of MgSO4 to neutralize theKOH formed during the reaction. Needles, m. 213-4°. o-Iodo-p-aminobenzoic acid,from the preceding compound and HCl, or by reducing the nitro acid with SnCl2 inpresence of glacial AcOH. Needles, m. and decomposes 180°. Hydrochloride, welldeveloped rods, decomposes in air. Silver salt, small needles, darkens rapidly on exposure to light. Methyl ester, needles, m. 112°.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Derivatives of o-Iodo-p-toluidine and of o-Iodo-p-nitrobenzoic Acid with Monoand Polyvalent Iodine》. Authors are Willgerodt, C.; Gartner, Rudolf.The article about the compound:1,2-Benzisoxazolecas:271-95-4,SMILESS:C12=CC=CC=C1ON=C2).Formula: C7H5NO. Through the article, more information about this compound (cas:271-95-4) is conveyed.

o-Iodo-p-toluidine, MeC6H3INH2, from 2-iodo-4-nitro-1-toluene and Fe(OH)2, in presence of aqueous NH3. Long, colorless needles, m. 37°. It is a very feeble base and its salts are decomposed by H2O. Hydrochloride, long, dark needles. Sulphate, lustrous plates. Nitrate, well developed, rhombic crystals, less soluble than the salts described above. Oxalate, small, rhombic crystals, m. and decomposes 103°. Carbamide, well developed, rhombic crystals, m. 194°. Nitrosocarbamide, yellow, lustrous needles, m. and decomposes 99°. It is unstable in air. Acetyl derivative,MeC6H3INHAc, colorless, interlaced needles, m. 130°. In alkaline soluble KMnO4 converts it into o-iodop-acetaminobenzoic acid (see below). With Cl it forms the iodo-dichloride, yellow needles, decomposes about 100°. Phenyl-p-acetaminotolyliodinium hydroxide, MeC6H3 (NHAc)IPhOH, from the preceding compound and HgPh2; alkaline. Iodide, pale yellow needles, m. 145°. It is unstable in air. Bromide, colorless rods, m. 159.5-60°. Bichromate, reddish brown needles, decomposes 80°. Chloroplatinate, small, yellow crystals, decomposes 110°, m. and evolves gas 125°. 2-Iodo-4-nitro-1-toluene, with HNO3 (d. 1.28), at 110-5° yields o-iodo-p-nitrobenzoic acid, O2NC6H3ICO2H; very long, pale yellow needles, m. 142°. Silver salt, colorless needles, unstable in air. Barium salt, crystals with I H2O. Methyl ester, long needles, m. 89°. Ethyl ester, large, highly lustrous rods, m. 44°. Chloride, yellow needles, b18 196°. Amide, yellow, rhombic crystals, m. 205°. o-Iodo-p-nitrobenzophenone, O2NC6H3IBz, from the chloride, AlCl3 and C6H6. Bundles of small needles, m. 90-1°. Oxime, from EtOH and HONH3Cl. Small rods, m. 161-1.5°. Indoxazene, formula (I) below, from the ketone, HONH3Cland alkali. Small, rhombic crystals, m. 139°. p-Nitrobenzoic acid o-iodo dichloride,yellow needles. Iodoso derivative (II) or (III), from the preceding compound and NaOH. Colorless, interlaced needles; various specimens m. 190-201°. It gives yellow solutionswith alkalies and concentrate H2SO4; when heated the latter solution liberates I. In Ac2Oand PhNH2 the color is red; after adding H2O the liquid shows a green fluorescence. The acid is stable towards boiling HCO2H, but Ac2O converts it into the iodo-nitrobenzoic acid. By the action of NaOH it yields NaIO3, and sodium iodonitrobenzoateand p-nitrobenzoate. The following derivatives of the iodoso acid have been prepared.Sodium salt, brown plates. Silver salt, small needles, explodes when heated. Bariumsalt, yellow needles. Copper salt, light green and amorphous. Lead salt, yellow powder. Methyl ester, small, interlaced needles, m. 180-1°. Iododichloride, yellow and crystalline. o-lodoxy-p-nitrobenzoic acid, O2IC6H3(NO2)CO2H, from the iodosoacid and KMnO4 in acid solution, or from NaOCl. Colorless needles, m. and explodesslightly 205°. It decomposes carbonates as also does the iodoso acid, and has a sourtaste. Silver salt, small needles, explodes violently when heated. Lead salt, paleyellow and amorphous. o-Iodo-p-acetaminobenzoic acid, AcNHC6H3ICO2H, from theiodoacettoluidide described above and KMnO4, in presence of MgSO4 to neutralize theKOH formed during the reaction. Needles, m. 213-4°. o-Iodo-p-aminobenzoic acid,from the preceding compound and HCl, or by reducing the nitro acid with SnCl2 inpresence of glacial AcOH. Needles, m. and decomposes 180°. Hydrochloride, welldeveloped rods, decomposes in air. Silver salt, small needles, darkens rapidly on exposure to light. Methyl ester, needles, m. 112°.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Formation and constitution of indoxazenes》. Authors are Lindemann, Hans; Pickert, Walter.The article about the compound:1,2-Benzisoxazolecas:271-95-4,SMILESS:C12=CC=CC=C1ON=C2).COA of Formula: C7H5NO. Through the article, more information about this compound (cas:271-95-4) is conveyed.

Heating o-HOC6H4CMeNOAc with NaOH on the H2O bath gives 2-methylindoxazene (I); with an excess of NaOH the corresponding oxime is obtained. 2-Hydroxy-4,6-dimethylbenzaldoxime, m. 130°; Ac derivative, m, 109°; with the calculated amount of NaOH this gives 3,5-dimethylindoxazene (II), b14 117°; with 20% NaOH on the H2O bath II gives 2-hydroxy-4,6-dimethylbenzonitrile, m. 180° (Ac derivative, m. 54°). Reduction of 2,4-dimethylindoxazene (III) in AcOH with Pd on BaSO4. gives 5,2-Me(OH)C6H3COMe; in absolute Et2O the corresponding imine, yellow, m. 167° (decomposition) is formed. In concentrated H2SO4-HNO3, II gives a 4-nitro derivative, m. 112°; NaOH transforms this into 2-hydroxy-4,6-dimethyl-5-nitrobenzonitrile, m. 193°. Indoxazene, d420.4 1.1729, n 1.5554, 1.56161, 1.57721 and 1.59124 for α, D, β and γ at 20.4°; 1, d419.9 1.1260, n 1.54472, 1.55098, 1.56624, 1.58074 at 19.9°; 111, d419.8 1.0955, n 1.53887, 1.54461, 1.55841, – at 19.8°; II, d420.2 1.1061, n, 1.54755, 1.55362, 1.56823, 1.58186 at 20.2°. The constitutions of these compounds are discussed in the light of the spectrochem. data.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Lewis acid-catalyzed [4+2] annulation between propargylic alcohols with benzo[d]isoxazoles, published in 2017, which mentions a compound: 271-95-4, Name is 1,2-Benzisoxazole, Molecular C7H5NO, Quality Control of 1,2-Benzisoxazole.

An unprecedented copper(II) trifluoromethanesulfonate-catalyzed [4+2] cascade annulation of propargylic alcs. with benzo[d]isoxazoles proceeded through a sequential ring opening/Meyer-Schuster rearrangement/intermol. cyclization. This protocol tolerated a broad variety of functional groups, offers a versatile, modular and atom-economical access to a new class of fascinating quinoline derivatives in good yields under mild conditions. The transformation could be scaled up to a gram scale efficiently, thus highlighting the synthetic utility of this methodol.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Gazzetta Chimica Italiana called Reactions with hydrazoic acid in sulfuric acid solutions. XIX. Formation of oxazoles and isoxazoles, Author is Caronna, Gaetano; Palazzo, Salvatore, which mentions a compound: 271-95-4, SMILESS is C12=CC=CC=C1ON=C2, Molecular C7H5NO, Application In Synthesis of 1,2-Benzisoxazole.

cf. CA 45, 2007b; 52, 15481c. The addition of HN3 to o-hydroxy aldehydes occurred without addition of the entire mol. of HN3. 2,5-HO(O2N)C6H3CHO (5 g.) added to 50 ml. CHCl3 and the yellow solution stratified with 15 ml. concentrated H2SO4 (d. 1.84), treated portionwise with 4.2 g. NaN3 with evolution of N and the mixture kept 12 hrs., the colorless CHCl3 layer decanted and the residue washed by decantation with CHCl3, poured slowly onto ice and the H2O-washed product crystallized (alc., C) gave 5-nitro-1,2-benzisoxazole (I), m. 126-7°, also obtained from the CHCl3 mother liquors to give a final yield of 85%. I hydrolyzed in dilute alkali and the orange red solution acidified with dilute HCl gave 2,5-HO(O2N)C6H3CN, m. 190-4°. The original dilute H2SO4 mother liquor made alk. with Na2CO3 and extracted repeatedly with Et2O, the extract evaporated and the residue crystallized from alc. yielded authentic 2-amino-5-nitrobenzoxazole, m. 288°. 5,2-Cl(OH)C6H3CHO (5 g.) in 30 ml. CHCl3 and 10 ml. concentrated H2SO4 treated portionwise with 4.5 g. HN3 and the mixture worked up as before gave 5-chloro-1,2-benzisoxazole, m. 70°, hydrolyzed to the corresponding 5,2-Cl(O2N)C6H3CN, m. 164-5° (H2O), and 2-amino-5-chlorobenzoxazole, m. 184°, together with a small amount of 5,2-Cl(HO)C6H3CN. 2,3,5-HO(Cl2)C6H2CHO (5 g.) in 30 ml. CHCl3, stratified with 30 ml. concentrated H2SO4 and treated portionwise with 4 g. NaN3 yielded, on working up, 5,7-dichloro-1,2-benzisoxazole, m. 107°, converted by alk. hydrolysis to 2,3,5-HO(Cl2)C6H2CN, m. 139°, and 2-amino-5,7-dichlorobenzoxazole, m. 251°. The average yields of benzisoxazoles from the corresponding aldehydes were about 90%. A probable mechanism for the cyclization was discussed.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Aminobenzothiazoles. XI. Synthesis of 5,4′-disubstituted 1-anilinobenzothiazoles from nuclear substituted thiocarbenilides》. Authors are Dyson, George M.; Hunter, Robert F.; Soyka, Charles.The article about the compound:1,2-Benzisoxazolecas:271-95-4,SMILESS:C12=CC=CC=C1ON=C2).Reference of 1,2-Benzisoxazole. Through the article, more information about this compound (cas:271-95-4) is conveyed.

cf. C. A. 23, 835. (p-BrC6H4NH)2CS and Br in CHCl3 yield a perbromide, which, on heating, gives a hydropentabromide(I), C13H8N2Br2S.HBr.Br4, orange-red needles, m. 170° (decomposition) and rapidly loses Br on exposure to moist air suspended in H2SO3 and treated with SO2, there results 5,4′-dibromo-1-anilinobenzothiazole(II), m. 221°; Ac derivative, m. 205-6°; HBr salt, m. 250° (decomposition); Br gives I. 1-Chloro-5-bromobenzothiazole, m. 89°, b13 157-9°, results by heating p-BrC6H4NCS and PCl5 30-40 hrs. at 170-80° warming with p-BrC6H4NH2 gives II. p-BrC6H4NHCSNHPh and Br in CHCl3 give the hydrotribromide, m. 148° (decomposition), which is reduced to 4′-bromo-1-anilinobenzothiazole (III), m. 214-5°, also obtained from 1-chlorobenzothiazole and p-BrC6H4NH2. Bromination of III gives II. 1-Anilinobenzothiazole yields a hexabromide, m. 140°, which yields II on being dissolved in boiling absolute EtOH. Hugershoff’s dibromoanilinobenzothiazole (Ber. 36, 3121(1903)) appears to consist mainly of II, although the m. p. could not be raised above 200°. Bromination of II gives an unstable orange hexabromide, m. 254°, which gives with hot absolute EtOH a tetra-Br substitution derivative, m. 196-8°. (p-ClC6H4NH)2CS and Br in CHCl3 yield a hydrotribromide, orange, m. 165-7° (decompm); reduction gives 5,4′-dichloro-1-aminobenzothiazole, m. 224°; Ac derivative, m. 186-7°; HBr salt. yellow, m. 217°; hexabromide, orange, m. 263° (decomposition). p-ClC6H4NHCSNHPh yields a Br addition compound, orange, m. 130° (decomposition); 4′-chloro-1-anilinobenzothiazole, m. 196°; this is also obtained from 1-chlorobenzothiazole and p-ClC6H4NH2. (p-IC6H4NH)2CS and Br in CHCl3 yield a red bromide, m. 185°, and a yellow, m. 211°; both, on reduction, yield 5,4′-diiodo-1-anilinobenzothiazole, m. 193° (decomposition); this also results by treating 1-anilinobenzothiazole in AcOH with ICl, warming the solution and diluting with H2O. (p-FC6H4NH)2CS gives a hydrotribromide, orange, m. 150-2° (decomposition); 5,4′-difluoro-1-anilinobenzothiazole, m. 227-8°. 5,4′-Dinitro-1-anilinobenzothiazole, brilliant yellow, in. 280°; this also results on nitration of 1-anilinobenzothiazole. (p-NCC6H4NH)2CS and Br give an addition product, golden, m. 159-60° (decomposition): 5,4′-dicyano-1-anilinobenzothiazole, m. 222°. (p-EtO2CC6H4NH)2CS yields a hydropentabromide, orange, m. 110° (decompn); reduction gives Et 1-anilinobenzothiazole-5,4′-dicarboxylate, m. 190-2°; hydrolysis gives the free acid, does not m. 290°. (p-MeOC6H4NH)2CS yields a brick-red bromide, m. 137° (decomposition), reduced to a dibromo-5,4′-dimethoxy-1-anilinobenzothiazole, m. 240°. PhNHCSNAcPh yields a hydrotribromide, orange, m. 167° (decomposition); the same compound is obtained from 1-acetanilinobenzothiazole, HBr and Br (Hugershoff, Ber. 36, 3136(1903)); Br in CHCl3 gives an orange hexa-Br addition compound, m. 163° (decomposition).

This literature about this compound(271-95-4)Reference of 1,2-Benzisoxazolehas given us a lot of inspiration, and I hope that the research on this compound(1,2-Benzisoxazole) can be further advanced. Maybe we can get more compounds in a similar way.

Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Benzisoxazoles. III》. Authors are Borsche, Walther; Scriba, Wilhelm.The article about the compound:1,2-Benzisoxazolecas:271-95-4,SMILESS:C12=CC=CC=C1ON=C2).Application In Synthesis of 1,2-Benzisoxazole. Through the article, more information about this compound (cas:271-95-4) is conveyed.

cf. C. A. 33, 8197.5. Meyer (Cathcart and M., Ber. 25, 3291 (1892)) was of the opinion that benzisoxazoles could not be prepared from oximes of o-acylated halo- or nitrobenzenes unless the radical XC6H4C(:NOH) is bound with a neg. group. It is now shown that this is not true. o-BrC6H4CN and MeMgI give 85% of 2-BrC6H4Ac, b16 118-20°; oxime (I), m. 129°. 2-BrC6H4CO2Me and MeMgI give some dimethyl-2-bromophenylcarbinol, b16 128-30°; BrC6H4Ac was not formed. Heating I with KOH in 50% MeOH gives 80% of 3-methylbenzisoxazole, b15 104-8°. o-BrC6H4CN and EtMgBr give 90% of 2-bromopropiophenone, yellowish oil, b16 135-40°; 2,4-dinitrophenylhydrazone, orange-yellow, m. 115-16°; oxime, b16 164-72°; with KOH in 50% MeOH (9 h. at 120°) there results a mixture of unchanged oxime and ethylindoxazene. o-BrC6H4CN (18.2 g.) and PhCH2MgCl give about 12 g. of 2-bromophenyl benzyl ketone, b15 206-8° (2,4-dinitrophenylhydrazone, orange, m. 149°; oxime, m. 116°); KOH in 50% MeOH (8 h. at 110-15°) gives 85% of 3-benzylbenzisoxazole, m. 87°. 4,3-Br(H2N)C6H3Me gives about 70% of 3-cyano-4-bromotoluene, m. 65°; MeMgI gives 3-acetyl-4-bromotoluene, b15 132-6°; 2,4-dinitrophenylhydrazone, orange, m. 170°; oxime, m. 131-2° (cf. Claus, J. prakt. Chem. 46, 26(1892), who states that it could not be converted to II); KOH in 50% MeOH (9 h. at 150°) gives 3,5-dimethylbenzisoxazole (II), b14 116-18° (NO2 derivative, m. 72°). 2-ClC6H4CN (6.4 g.) gives 4 g. 2-ClC6H4Ac; 2,4-dinitrophenylhydrazone, dark yellow, m. 206°; semicarbazone, m. 178-9°. 2-BrC6H4Ac, BzH and 10% NaOH in MeOH give 2-cinnamoylbromobenzene, b14 234-8°, as a yellow, viscous oil; 2,4-dinitrophenylhydrazone, red, m. 236-7°; an oxime could not be prepared 6,3-Br (O2N)C6H3Ac (4.88 g.) and 4 g. PhNHNH2.HCl in MeOH, heated 18 h. at 150°, give 3.1 g. of 3-methyl-1-phenyl-5-nitroisoindazole, yellow, m. 131-2°; catalytic reduction gives the 5-NH2 derivative, m. 127-8° (Bz derivative, m. 160-1°); a byproduct, yellow, m. 336°, is probably the corresponding azoxy compound Removal of the NH2 group gives 3-methyl-1-phenylisoindazole, m. 73-4°.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI