Properties and Exciting Facts About 2-Methylbenzofuran

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Photochromic diarylethene derivatives having benzofuran heteroaryl groups, bis(2-methyl-1-benzofuran-3-yl)perfluorocyclopentene and bis(2-butyl-1- benzofuran-3-yl)perfluorocyclopentene, were synthesized, and their photochromic performance was examined in hexane solution as well as in the single-crystalline phase. The compounds exhibited photochromic reactivity even in the single-crystalline phase.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H331O – PubChem

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Brominated flame retardant (BFR), which containing in printed circuit boards (WPCBs), brings a series of environmental and health problems. Hydrothermal technology was applied to decompose brominated epoxy resin in WPCBs at subcritical or supercritical water conditions. The brominated epoxy resin was decomposed into oil and the environmental influence of BFR was eliminated. The experiment was carried out in a 5.7 ml tube reactor and heated by a salt-bath. The variation of degradation rate of brominated epoxy resin with reaction temperature, time and additives were studied. The compositions of liquid products were analyzed by gas chromatography-mass spectrometry (GC-MS). When reaction temperature exceeded 300 C, retention time stayed over 30 min and alkaline additive existed, more than 80% brominated epoxy resin could be mainly decomposed into phenol, which can be used as chemical material. Two different hydrothermal decomposition pathways were discussed according to the characterization of products. The results indicated that brominated epoxy resin in WPCBs could be handled effectively by hydrothermal decomposition.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H337O – PubChem

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Tomato juice contains volatile compounds that are originally detected in fruit, such as terpenes, and others that are originated during processing by lipoxygenase activity, carotenoid co-oxidation and Maillard reaction that can be activated during the thermal treatments. This paper reports the analysis of the volatile compounds of tomato juice sampled by solid phase microextraction (SPME) and the optimization of the blanching parameters in tomato juice, using the volatile compounds as markers. One hundred and ninety volatile compounds, including ketones, aldehydes, alcohols, esters, ethers, hydrocarbons, sulfur, nitrogen and oxygen compounds, phenols, oxygen-containing heterocyclic compounds, free acids and lactones, were identified or tentatively identified by the GC-MS technique. The thermal treatment mainly modifies saturated and unsaturated C6 alcohols and aldehydes, esters, ketones and carotenoid derivatives. The optimal conditions for the blanching, selected by response surface modelling (RSM), were 67C for 24 min and 86C for 3.5 min for the cold break and the hot break treatments, respectively. Copyright (C) 2000 Elsevier Science Ltd.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H273O – PubChem

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4,6-Dinitrobenzofuroxan (DNBF) and 4,6-dinitrobenzofurazan (DNBZ) behave as conventional electrophiles toward 2,5-dimethylpyrrole, 2,5-dimethylthiophene, and 2-methylbenzofuran, adding to the unsubstituted beta-carbon to form the corresponding ? adducts in Me2SO.In contrast reactions with 2,5-dimethylfuran result in electrophilic substitution of a methyl group as the only observed process.The mechanism of the latter reaction is discussed with reference to previously reported results.This leads to some reconsideration of current notions regarding the mechanism of electrophilic side-chain reactions of 2,5-dimethyl five-membered ring heterocycles.It is also concluded that DNBF and DNBZ have an electrophilic character of the same order as that of 2,4-dinitrobenzenediazonium cation.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H290O – PubChem

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Andosols are usually formed from volcanic substrates, with thick A horizons high in organic carbon mainly in the form of stabilized humic fractions. The peculiar properties of these soils are, to large extent, affected by poorly crystalline materials like allophanes, imogolite and other Fe and Al oxyhydroxides that induce intense organo-mineral interactions which are considered to play a relevant role in OM protection against biodegradation as regards other soils developed under similar climatic conditions. Little is known about the molecular composition of this stabilized OM in a soil scenario often considered as an efficient C-sink in terms of C sequestration processes. Whole soil samples in addition to isolated humic and fulvic acids from organic A horizons of three soils with andic properties and one non-andic soil (Sodic Cambisol) from the island of Tenerife (Canary Islands, Spain) were analysed by double shot pyrolysis-gas chromatography-mass spectrometry (Py-GC/MS) in order to get some insight on the molecular composition of different structural domains of progressive structural stability. Clear differences were found between soils, both in thermal desorption and pyrolysis behaviour of humic substances. In general the results suggest large yields of aliphatic (both alkyl and carbohydrate-derived pyrolysis compounds) pointing to high-performance processes of incorporation of aliphatic humic constituents in andosols probably favoured by interactions with amorphous minerals, whereas in non-andic soils the latter are comparatively less stabilized and are removed in early pyrolysis stages as if they occurred as loosely joined, thermoevaporation-released products. In fact, compared to Cambisol, humic and fulvic acids from andic soils led to comparatively richer pyrograms and compound assemblages. The lack of similar amounts of these loosely joined, mainly aliphatic structures after thermal desorption of the whole andic soils indicate an origin for humic substances based on rapid sequestration of C-forms of recent (litter or microbial) origin.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H119O – PubChem

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A new synthetic method for the preparation of benzofurans has been developed. The key step of this method is the [3,3]-sigmatropic rearrangement of N-trifluoroacetyl-ene-hydroxylamines, which was triggered by acylation of oxime ethers. TFAA has been proved to be the best reagent to induce [3,3]-sigmatropic rearrangement for the synthesis of cyclic or acyclic dihydrobenzofurans. On the other hand, the TFAT-DMAP system is found to be the most effective for constructing various benzofurans. Synthetic utility of this reaction is demonstrated by the short synthesis of natural benzofurans without protection of the hydroxy group. The synthesis of Stemofuran A was accomplished via condensation of ketones with aryloxyamine and subsequent reaction with TFAT-DMAP in a four-step synthesis with 72% overall yield. Similarly, Eupomatenoid 6 and Coumestan were synthesized through the reaction of oxime ether with TFAT-DMAP. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H284O – PubChem

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In this work, two catalytic systems were applied for the production of 5-(hydroxymethyl)-furfural (HMF) from different water-soluble carbohydrates. These systems combined Lewis (ZnCl2 and AlCl3) and Br°nsted (HCl) acids in a biphasic system composed of an extraction solvent (ES) and a reaction solvent (RS). Tetrahydrofuran (THF) was used to control yield losses that are due to undesirable side reactions by promoting the continuous extraction of HMF from the aqueous phase, which was nearly saturated with sodium chloride (NaClaq). HMF production was enhanced when high temperatures (180 C) and high ES/RS ratios (10) were employed in short reaction times (60 min). The combination of Lewis and Br°nsted acids and the use of the THF/NaClaq biphasic system proved to be the right choice for HMF production. AlCl3/HCl was best for glucose dehydration while ZnCl2/HCl gave higher HMF yields from sucrose and sugarcane molasses (65.6 and 49.6%, respectively). Compared to synthetic mixture containing the same amount of sugars, no matrix interference was observed during dehydration of sugarcane molasses. ZnCl2/HCl humins were primarily composed of furan derivatives, whereas AlCl3/HCl humins had higher molecular mass and benzofurans content, which were a result of the higher acidity of this reaction system.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H116O – PubChem

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Electron-rich aromatic C-H bonds undergo regioselective chlorination and bromination in the presence of CuX2, LiX (X = Cl, Br) and molecular oxygen. Preliminary mechanistic insights suggest that the bromination and chlorination reactions proceed by different pathways.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H333O – PubChem

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Abstract Boron-containing phenolic resin (BPR) is a kind of the ablative resins with high-performance. Due to the lack of the exact knowledge concerning the pyrolysis mechanism of BPR, its development and application are greatly impeded. In the present paper, the chemical structure of the cured BPR and its structural evolution at high temperatures are investigated to clarify the reason for the high char yield of BPR. The results indicate that the high char yield of BPR is mainly attributed to the phenyl borates formed during curing, which can block parts of phenolic hydroxyl groups, and effectively inhibit their thermal decomposition reaction. Boron oxide is formed on the surface of carbonization products by the cleavage of O-C bonds from phenyl borates via pyrolysis, which avoids the release of volatile carbon dioxide and reduces the development of micro-structural defects of carbonization products. Introducing boron into PR improves the graphitization degree and graphite crystallites of carbonization products, which promotes the formation of a more ordered glassy carbon during pyrolysis. This study provides a new vision for the understanding of the high char yield of BPR, which makes it possible to develop a new ablative resin through molecular design.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H317O – PubChem

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The pyrolysis behavior of aluminum alginate is compared with that of alginic acid. The thermal degradation and pyrolysis behavior of aluminum alginate have been studied using a thermogravimetric analyzer coupled with Fourier transform infrared analysis and mass spectrometry (TG-FTIR-MS) and a pyrolysis-gas chromatography-mass spectrometry (Py-GC-MS), respectively. TG-FTIR-MS and Py-GC-MS results indicated that the aluminum ions influenced the devolatilization gas products upon pyrolysis process. The pyrolysis of alginic acid was found to yield much more kinds of products than aluminum alginate was. And it suggested that the aluminum ions could strongly catalyze the fragments formed in the pyrolysis process of aluminum alginate to produce the less molecular weight and more stable products, such as carbon dioxide and furfural. The results indicated that the aluminum ions had the catalysis effect on the pyrolysis process of aluminum alginate. The possible thermal degradation mechanism of aluminum alginate was proposed according to the results of Py-GC-MS of aluminum alginate. The results of our study provide useful information for understanding the flame retardant mechanism of alginates.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H184O – PubChem