552-86-3

Usage

Uses

Used in Analytical Chemistry:
2,2'-Furoin is used as a fluorogenic reagent for the selective and sensitive liquid chromatographic determination of various guanidines. Its chemical properties allow it to react with guanidines, producing a fluorescent signal that can be detected and quantified, making it a valuable tool in the analysis of these compounds.
Used in Pharmaceutical Industry:
2,2'-Furoin is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and reactivity make it a versatile building block for the development of new drugs and therapeutic agents.
Used in Chemical Research:
Due to its distinctive chemical properties, 2,2'-furoin is also used in chemical research as a model compound for studying various reaction mechanisms and exploring new synthetic routes. This contributes to the advancement of knowledge in organic chemistry and the development of novel chemical processes.

Preparation

2,2'-Furoin is prepared by the condensation of furfural with benzoin under the catalysis of potassium cyanide. 8L of water, 3L of ethanol, and 4kg of furfural were heated to 60-70°C on a water bath, and a solution of 200g potassium cyanide dissolved in 600lookchemml of water was slowly added under stirring. The reaction exotherm automatically heated up to 80-90 ° C, and crystals were precipitated later. After standing, filter, wash the crystals with water and methanol until the washing is colorless, and recrystallize with ethanol, which is the finished product of bran coupler.

Purification Methods

It crystallises from MeOH (charcoal) and distils in a vacuum. [Hartman & Dickey J Am Chem Soc 55 1228 1933.] The (-)-enantiomer crystallises from toluene or EtOH with m 131-131o, and [] 20 -4.9o (dioxane) [Neuberg et al. Arch Biochem 1 393 1943, Beilstein 19 H 204, 19 I 710, 19 II 224, 19 III/IV 2543.]

InChI:InChI=1/C10H8O4/c11-9(7-3-1-5-13-7)10(12)8-4-2-6-14-8/h1-6,9,11H/t9-/m1/s1

Upstream product

• 98-01-1 furfural 
• 151-50-8 potassium cyanide 
• 492-94-4 furil 
• 100956-82-9 1,2-di-[2]furyl-2-hydroxy-3-morpholino-propan-1-one 
• 5391-74-2 1-(phenylhydrazono)-propan-2-one 
• 64-17-5 ethanol 
• 59-43-8 vitamin B₁ 
• 96643-07-1 thiamine hydrochloride 
• 21659-48-3 β-furoin oxime 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 7732-18-5 water 
• 100-52-7 benzaldehyde 
• 292638-85-8 acrylic acid methyl ester 
• 140-88-5 ethyl acrylate 

Downstream Products

• 19021-42-2 bis-(2-nitro-stilben-4-yl)-diazene-N-oxide 
• 109448-28-4 2-p-toluidino-1,2-bis-[2]furyl-ethanone 
• 57490-73-0 2,3-di-furan-2-yl-quinoxaline 
• 492-94-4 furil 
• 36715-43-2 1-(furan-2-yl)-2-hydroxy-2-phenylethanone 
• 86352-16-1 2-(Furan-2-yl)-2-hydroxy-1-phenylethanone 
• 75501-66-5 2-hydroxy-1,2,3,5-tetraphenyl-1,5-pentanedione 
• 133527-90-9 3-(2,4-dichlorophenyl)-6,7-difuryl-5H-s-triazolo<3,4-b><1,3,4>thiadizine 
• 128742-85-8 2-phenylamino-1,2-di(2-furyl)ethan-1-one 
• 24386-17-2 2-amino-4,5-di-(2-furanyl)-furan-3-carbonitrile 
• 75-97-8 3,3-dimethyl-butan-2-one 
• 127628-72-2 1,2-Difuryl-1,2-dimethoxyethylene 
• 75-18-3 dimethylsulfide 
• 109610-92-6 5-bromo-2,2'-furil 

Relevant academic research and scientific papers

Recyclable Supported Carbene Catalysts for High-Yielding Self-Condensation of Furaldehydes into C10 and C12 Furoins

Two highly efficient and recyclable heterogeneous azolium catalyst systems, one grafted (g) onto the inorganic oxide (Silica) and the other onto the organic polymer [Merrifield's peptide or chloromethylated polystyrene (PS) resin], have been developed and employed to catalyze quantitative self-coupling (umpolung condensation) reactions of furfural and 5-hydroxymethylfurfural (HMF) into C10 and C12 furoins, respectively. Supported benzimidazolium ([BI]) salts bearing a long-chain alkyl substituent (i.e.; C12 dodecyl) on the azolium nitrogen atom, upon activation with a suitable base to generate the corresponding N-heterocyclic carbene (NHC) catalyst, are found to be far more effective catalysts for furaldehyde self-coupling reactions than the analogous catalysts carrying a short-chain alkyl substituent (i.e.; C1 methyl). Thus, supported NHC catalysts generated in situ from Silica-g-[BI]-C12 or PS-g-[BI]-C12-benzyl/base afford the C10 and C12 furoins in about 97% and 94% yield, respectively. By adopting a catalyst recycling procedure that involves activation of the precatalyst with a base to generate the NHC catalyst, catalysis in conversion of furaldehydes into furoins, and recycle of the catalyst by quenching the reaction with HCl to convert the catalyst back to the precatalyst, excellent recyclability has been achieved without loss of the catalytic activity after 10 cycles by maintaining essentially a constant furoin yield of 96-97% for all 10 cycles performed with both supported catalyst systems.

Recyclable montmorillonite-supported thiazolium ionic liquids for high-yielding and solvent-free upgrading of furfural and 5-hydroxymethylfurfural to C10 and C12 furoins

Six Na+/montmorillonite (MMT)-supported thiazolium (TM) ionic liquids (ILs), MMT-[TM], which are precatalysts to N-heterocyclic carbene (NHC) catalysts, have been synthesized and employed to catalyze the highly selective condensation of furfural (FF) and 5-hydroxymethylfurfural (HMF) into C10 and C12 furoins, respectively. Among them, five supported [TM] salts carrying the electron-donating group exhibit excellent catalytic activity. Thus, supported NHC catalysts, generated in situ from activation of MMT-[TM] with Et3N, afford C10 and C12 furoins in 97-99% and 97-98% yield, respectively. This condensation reaction is also carried out under solvent-free conditions, and the catalysts can be readily recycled, showing no noticeable loss in their catalytic activity over four consecutive recycles. Thus, these desired features possessed by the current catalyst system have enabled the development of the greener and more environmentally benign process for the upgrading of FF and HMF.

Hybrid catalysts based on N-heterocyclic carbene anchored on hierarchical zeolites

Hybrid materials have been synthesized by anchoring a N-heterocyclic carbene (NHC) precursor on different inorganic zeolitic supports with hierarchical porosity, in particular hierarchical HZSM-5 and SAPO-5. Hierarchical porous inorganic supports have been obtained both by top-down and bottom-up approaches and the role of hierarchical porosity has been evaluated. A detailed physico-chemical characterization has been performed on the organic-inorganic hybrids using a multi-technique approach (XRD, volumetric and thermogravimetric analysis, ssNMR and FTIR) in order to establish a structure-property relationship. The hybrids were tested in the benzoin condensation reaction of furfural, a base catalyzed reaction.

N-PEGylated Thiazolium Salt: A Green and Reusable Homogenous Organocatalyst for the Synthesis of Benzoins and Acyloins

N-PEGylated-thiazolium salt is used as efficient catalyst for the benzoin condensation. The catalyst was synthesized by reaction of activated polyethylene glycol 10,000 (PEG-10000) with 4-methyl-5-thiazoleethanol (sulfurol). Reaction mixture undergoes temperature-assisted phase transition and catalyst separated by simple filtration. After reaction course, catalyst can be recycled and reused without any apparent loss of activity which makes this process cost effective and hence ecofriendly. Synthesized benzoins and acyloins by this method have been characterized on the basis of melting point and 1H-NMR spectral studies. Graphic Abstract: [Figure not available: see fulltext.]

Synthesis of 1,10-decanediol diacetate and 1-decanol acetate from furfural

A green and efficient method was developed for upgrading furfural to 1,10-decanediol diacetate and 1-decanol acetate. 92% yield of the acetates was obtained through the tandem benzoin condensation and hydrodeoxygenation reaction. During the benzoin condensation, furfural was catalyzed into furoin in a quantitative yield by the immobilized NHC catalyst under solvent-free conditions. After dissolving the furoin intermediate in acetic acid, the Sc(OTf)3and Pd/C catalytic system was introduced for hydrodeoxygenation. The effects of reaction factors have been investigated in detail and the hydrodeoxygenation process has been explored by1H-NMR and GC-MS.

Sol-gel synthesis of ceria-zirconia-based high-entropy oxides as high-promotion catalysts for the synthesis of 1,2-diketones from aldehyde

Efficient Lewis-acid-catalyzed direct conversion of aldehydes to 1,2-diketones in the liquid phase was enabled by using newly designed and developed ceria–zirconia-based high-entropy oxides (HEOs) as the actual catalysts. The synergistic effect of various cations incorporated in the same oxide structure (framework) was partially responsible for the efficiency of multicationic materials compared to the corresponding single-cation oxide forms. Furthermore, a clear, linear relationship between the Lewis acidity and the catalytic activity of the HEOs was observed. Due to the developed strategy, exclusively diketone-selective, recyclable, versatile heterogeneous catalytic transformation of aldehydes can be realized under mild reaction conditions.

Total Synthesis of (+)-Hyacinthacine A1Using a Chemoselective Cross-Benzoin Reaction and a Furan Photooxygenation-Amine Cyclization Strategy

We report the shortest synthesis of glycosidase inhibitor (+)-hyacinthacine A1 using a highly chemoselective N-heterocyclic carbene-catalyzed cross-benzoin reaction as well as a furan photooxygenation-amine cyclization strategy. This is the first such cyclization on a furylic alcohol, an unprecedented reaction due to the notorious instability of the formed intermediates. The photooxygenation strategy was eventually incorporated into a three-step one-pot process that formed the requisite pyrrolizidine framework of (+)-hyacinthacine A1.

Method for preparing sebacic acid ester and derivatives thereof (by machine translation)

. Uses the compound of the formula, as the raw material, in the acid solvent selective hydrodeoxygenation to obtain.decanediol and n-decanol: and the method (I) is characterized in that the product is cheap and easily available, product in yield, high in purity, and suitable for industrial production 1,10 - in a simple, process route . The product obtained by the method has the advantages of high yield, high yield and low pollution, to the environment, and the corresponding alcohol, is obtained by saponification reaction. (by machine translation)

Oxazolium Salts as Organocatalysts for the Umpolung of Aldehydes

Oxazolium salts were successfully employed for the first time as organocatalysts for benzoin, Stetter, and redox esterification reactions. An N-mesityl oxazolium salt catalyzed homobenzoin reaction of aromatic, heteroaromatic, and aliphatic aldehydes delivered α-hydroxy ketones in high yields. This new type of catalyst proved remarkably effective for the Stetter reaction of challenging substrates such as β-alkyl-α,β-unsaturated ketones and electron-rich aromatic aldehydes in comparison to common thiazolium and triazolium salts.

Thiazole ionic liquid catalysis of furfural coupling into furoin

Furfural is an important platform compound and is a precursor for preparation of biology liquid fuel and many other important fine chemical products. However, furfural is mainly prepared by dehydration of C5 sugar. Though furfural is latent fuel for means of transportation, furfural is alkane with low carbon number and has characteristics of high fluctuation and low energy density. Thus, furfuralcannot become an ideal fuel additive. According to the invention, without a solvent, a thiazole ionic liquid with anions as weak acid radicals is utilized for catalysis of furfural coupling into furoin. Usually, an ionic liquid has the property of catalyzing furfural coupling into furoin only with the addition of alkali. As anions of the ionic liquid used in the reaction are weak acid radicals, the ionic liquid with weak acid radicals can complete catalytic action of the furfural coupling reaction and can achieve an ideal catalytic effect.