- Preparation and preliminary application of 5-HMF@SiO2 micro-particles
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A new approach for the surficial-modification of silica with 5-HMF as a functional molecule was first designed. The infrared spectrum, X-ray photoelectron spectroscopy and elemental analysis showed that the modified-SiO2 particles were successfully established. Full dispersion of SiO2 and the introduction of gallic acid were confirmed to be favorable for the 5-HMF content. The retention behavior of bovine serum albumin on the modified-SiO2 particle suggested that the novel particles could serve as a promising stationary phase on the identification of the particular proteins.
- Wang, Cheng,He, Huaizhen,Lin, Yuanyuan,Huang, Limin,Sun, Meng,Zhang, Tao,He, Langchong
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Read Online
- Preparation method of 5-halogenated methylfurfural
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The invention discloses a preparation method of 5-halogenated methylfurfural, which comprises the steps of (1) adding raw materials, choline chloride/choline bromide, an organic acid as a hydrogen bond donor, a metal salt and dichloroethane into a reactor, and carrying out stirring reaction at the temperature of 80-150 DEG C for 5-300 minutes to obtain a reaction phase composed of an upper layer and a lower layer, wherein the lower layer is an eutectic solvent phase, and the upper layer is a dichloroethane phase; and (2) enabling the eutectic solvent phase to be subjected to dichloroethane extraction and separation purification so as to obtain a product containing 5-halogenated methylfurfural. The selected raw materials are wide in source, low in price and easy to obtain; the reaction conditions are mild, and the reaction yield is high; and a novel thought is provided for researching the 5-halogenated methylfurfural and downstream products thereof in the future.
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Paragraph 0033-0034; 0051-0052
(2021/01/30)
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- Synthesis of various cyclopropyl methyl bromide and its derivatives from ketones and/or aldehydes and some β-dicarbonyl compounds in the presence of BrCN and Et3N
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The ultimate goal in this paper has been developed for the synthesis of structurally various bromomethyl cyclopropane via an α-bromoketone and/or aldehydes with ethyl cyanoacetate or malononitrile and cyanogen bromide (BrCN) in the presence of Et3N to give products in excellent yields within about 3?s. All structures were characterized by IR, 1H-NMR, 13C-NMR, and Mass spectroscopy techniques. The reaction mechanism was discussed.
- Gholizadeh, Saeed,Safa, Kazem D.,Noroozi Pesyan, Nader
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p. 1239 - 1253
(2019/04/27)
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- 5-hydroxymethylfurfural- and fluorescein-fused fluorescence probe of mast cells (RBL-2H3): Synthesis, photophysical properties, and bioimaging
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A fluorescent probe (Fluo-HMF) was developed via introduction of a furfural moiety into the fluorescein molecular skeleton, aiming at specially labeling cell membrane of mast cells. To illustrate its specificity, we designed and synthesized a series of fluorescent compounds based on fluorescein molecular skeleton. The fluorescent properties of Fluo-HMF were investigated, which were in accordance with theoretical calculations. Compared with other fluorescein derivatives, Fluo-HMF could specially label RBL-2H3 cells. The results suggested that Fluo-HMF could be used as a fluorescent probe for bioimaging on some related research of allergic mechanism.
- Huang, Limin,Wei, Di,Wu, Zibo,Hou, Yajing,Xie, Yitong,Liu, Zhenru,Wang, Cheng,Che, Delu,Lei, Yibo,He, Huaizhen
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p. 1963 - 1971
(2018/09/06)
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- Preparation of halogenated furfurals as intermediates in the carbohydrates to biofuel process
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Lignocellulose derived halogenated furfurals are important chemicals that can serve as starting materials for diverse products such as drugs, polymers and fuels, including fuel additives. In this paper a protocol for the synthesis of 5-chloromethyl furfural (CMF) and 5-bromomethyl furfural (BMF) is put forward. The proposed process is based on a two liquid phases reaction composed of an aqueous hydrochloric or hydrobromic acid phase and 1,2-dichloroethane (DCE) organic phase. We have optimized and compared the yields of CMF and BMF in an open flask and in a closed reaction vessels. Utilization of the close reaction vessel resulted in not only higher yields in a shorter reaction time but also eliminated the necessity of the customary lithium salts additives previously advocated for this process. These additives were required in the open reaction systems in order to achieve reasonable yields. While a closed reaction vessel was previously reported for the production of CMF, and in this work its production was further improved, it is the first time a close vessel protocol for the production of BMF has been reported. In addition, improvement of the substrate to organic solvent ratio has been carried while yields of halogenated furfurals were maintained almost intact. NMR and UV-vis spectroscopy were used for identification and quantification of the products.
- Meller, Elad,Aviv, Avishay,Aizenshtat, Zeev,Sasson, Yoel
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p. 36069 - 36076
(2016/05/19)
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- Facile synthesis of 5-hydroxymethylfurfural: A sustainable raw material for the synthesis of key intermediates toward 21,23-dioxaporphyrins
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In a simple and conceptually designed method for the dehydration of fructose on a solid support, 5-hydroxymethylfurfural (HMF) was synthesized in more than 95% isolated yield from fructose under very mild conditions at room temperature. The loading of fructose on the solid support reduced the intermolecular interactions between fructose/intermediates, diminished the formation of polymeric material (humin) and increased the selectivity towards HMF formation. The synthesized HMF was readily converted into key intermediates toward the simpler synthesis of 21,23-dioxaporphyrins.
- Rajmohan, Rajamani,Gayathri, Subramaniyan,Vairaprakash, Pothiappan
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p. 100401 - 100407
(2015/12/04)
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- Evaluation of carbohydrates and lignocellulosic biomass from different wood species as raw material for the synthesis of 5-bromomethyfurfural
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The influence of different parameters on the conversion of carbohydrates and biomass into the potential biofuel intermediate 5-bromomethylfurfural (BMF) has been studied. Our optimized conditions avoid the use of lithium salt additives, making this method cheaper and environmentally more benign compared to previously reported methods. Different wood species and their potential as a raw material in BMF and furfural production have also been evaluated. In addition, we report a very simple and efficient procedure for conversion of 5-hydroxymethylfurfural (HMF) into BMF or 5-chloromethylfurfural (CMF).
- Bredihhin, Aleksei,M?eorg, Uno,Vares, Lauri
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- Synthesis of 5-bromomethylfurfural from cellulose as a potential intermediate for biofuel
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Cellulose can be converted into 5-bromomethylfurfural (BMF), a brand new biofuel or biofuel intermediate, in 80 yield by treatment with HBr and LiBr and continuous extraction with toluene. From other carbohydrates and straw, BMF was also obtained in high yields. The mechanism of BMF formation was investigated, and the results indicate that this furfural is formed during the depolymerization of cellulose and that glucose is not an intermediate.
- Kumari, Nitee,Olesen, Jens Kruse,Pedersen, Christian M.,Bols, Mikael
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experimental part
p. 1266 - 1270
(2011/04/17)
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- 3-deoxy-glucosone is an intermediate in the formation of furfurals from D-glucose.
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The acid-catalyzed dehydration of glucose to hydroxymethylfurfural (6) can occur via two possible mechanisms. 3-deoxy-D-erythro-hex-2-ulose (3) is found to be an intermediate in the formation of 6 from glucose (1). This finding implies that elimination of the glucose 3-OH group is the important step, rather than isomerization of the carbonyl group.
- Jadhav, Harishchandra,Pedersen, Christian Marcus,S?lling, Theis,Bols, Mikael
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scheme or table
p. 1049 - 1051
(2012/04/10)
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- PYRAZOLOPYRIDINE DERIVATIVES AS ANTICANCER AGENT
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The present invention concerns compounds of following general formula (I): (Formula I) and their pharmaceutically acceptable salts, their method of preparation and their uses, notably as anticancer agent.
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Page/Page column 87
(2011/05/05)
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- Direct, high-yield conversion of cellulose into biofuel
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(Chemical Equation Presented) Fueling up with furans: Cellulose can be converted into furanic biofuels in unprecedented yields using an inexpensive, simple process involving concurrent hydrolysis, dehydration, and chlorine substitution reactions coupled with continuous extraction into an organic phase (see scheme). Furanic ethers, such as those that can be derived from the products above, are known diesel additives.
- Mascal, Mark,Nikitin, Edward B.
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body text
p. 7924 - 7926
(2009/04/18)
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- Structure-activity relationships of phenyl-furanyl-rhodanines as inhibitors of RNA polymerase with antibacterial activity on biofilms
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The dramatic rise of antibiotic-resistant bacteria over the past two decades has stressed the need for completely novel classes of antibacterial agents. Accordingly, recent advances in the study of prokaryotic transcription open new opportunities for such molecules. This paper reports the structure-activity relationships of a series of phenyl-furanyl-rhodanines (PFRs) as antibacterial inhibitors of RNA polymerase (RNAP). The molecules have been evaluated for their ability to inhibit transcription and affect growth of bacteria living in suspension or in a biofilm and for their propensity to interact with serum albumin, a critical parameter for antibacterial drug discovery. The most active of these molecules inhibit Escherichia coli RNAP transcription at concentrations of ≤10 μM and have promising activities against various Gram-positive pathogens including Staphylococcus epidermidis biofilms, a major cause of nosocomial infection.
- Villain-Guillot, Philippe,Gualtieri, Maxime,Bastide, Lionel,Roquet, Fran?oise,Martinez, Jean,Amblard, Muriel,Pugniere, Martine,Leonetti, Jean-Paul
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p. 4195 - 4204
(2008/03/15)
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- Synthese du 5-bromomethyl- et du 5-chloromethyl-2-furannecarboxaldehyde
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The action of hydrogen halides, sulfur and phosphorous halides, and halotrimethylsilanes on 5-(hydroxymethyl)-2-furancarboxaldehyde (1) led to the corresponding 5-(chloromethyl)- (2) or 5-(bromomethyl)-2-furancarboxaldehyde (3).Thus, treatment of 1 in diethyl ether solution with gaseous dry hydrogen chloride under very mild experimental conditions led to high yields of 2.The selective and quantitative conversion of 1 into 3 was achieved with bromotrimethylsilane.In the same manner, chlorotrimethylsilane gave high yields of 2 from 1.The latter compound was obtained by acid-catalyzed dehydration of D-fructose in dimethyl sulfoxide, and then converted into 2 without prior purification.
- Sanda, Komla,Rigal, Luc,Gaset, Antoine
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- Process for producing 5-halomethylfurfural
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A process for producing 5-halomethylfurfural represented by the formula, STR1 wherein X is Cl or Br, which comprises carrying out a acid-decomposition of saccharide in a water/organic solvent/magnesium halide system with hydrochloric acid, sulfuric acid, hydrogen chloride or other mineral acid in the presence or absence of surface active agent as a catalyst. The 5-halomethylfurfural is useful as an intermediate of medicines, agricultural chemicals, perfumes and the like.
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- NOUVELLE METHODE DE PREPARATION DU 5-HYDROXYMETHYL-2-FURALDEHYDE PAR ACTION DE SELS D'AMMONIUM OU D'IMMONIUM SUR LES MONO-, OLIGO- ET POLY-SACCHARIDES. ACCES DIRECT AUX 5-HALOGENOMETHYL-2-FURALDEHYDES
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In a new and simple process for preparing 5-hydroxymethyl-2-furaldehyde from mono-, oligo- and poly-saccharides, which uses immonium or ammonium salts, direct heating of the reagent and the starting material, both in solid phase, gave directly 5-hydroxymethyl-2-furaldehyde with a good purity, avoiding production of secondary products.The use of a polymeric form of the reagent constitutes an extension of the method toward an eventual industrial application.Under special conditions, a one-pot dehydration-halogenation sequence gave 5-bromomethyl-(or 5-chloromethyl)-2-furaldehyde.
- Fayet, Catherine,Gelas, Jacques
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- AN IMPROVED METHOD FOR THE CONVERSION OF SACCHARIDES INTO FURFURAL DERIVATIVES
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An improved method for the preparation of furan compounds by dehydrating saccharides with hydrochloric acid either in a mixture containing water, organic solvent and a catalytic amount of a surface active agent or in the presence of magnesium halide is described.
- Hamada, Kazuhiko,Yoshihara, Hiroshi,Suzukamo, Gohfu
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p. 617 - 618
(2007/10/02)
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