6078-02-0

Basic information

• Product Name: Phenol, 2-[(2-furanylmethylene)amino]-
• CAS NO: 6078-02-0
• Molecular Formula: C11H9NO2
• Molecular Weight: 187.198
• Mol File: 6078-02-0.mol

Chemical Properties

• CAS DataBase Reference: Phenol, 2-[(2-furanylmethylene)amino]-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol, 2-[(2-furanylmethylene)amino]-(6078-02-0)
• EPA Substance Registry System: Phenol, 2-[(2-furanylmethylene)amino]-(6078-02-0)

Safety Data

• Hazardous Substances Data: 6078-02-0(Hazardous Substances Data)

Upstream product

• 98-01-1 furfural 
• 95-55-6 2-amino-phenol 

Downstream Products

• 86818-41-9 N-(2-hydroxyphenyl)-2-furfurylamine 
• 881-60-7 2-(furan-2-yl)benzoxazole 
• 192565-63-2 (S)-S-ethyl 3-(2'-furyl)-3-[(2'-hydroxyphenyl)amino]propanethioate 

Relevant articles and documents

Novel R3M (M = Si, Ge) substituted furan and thiophene-derived aldimines: Synthesis, electrochemistry, and biological activity

New furan and thiophene derivatives of aldimines o-HO-C6H4N[dbnd]CHC4H4X(R) (X = O, S; R = H, SiMe3, SiEt3, GeMe3, GeEt3) were synthesized by condensation of o-aminoph

A highly efficient environmental-friendly adsorbent based on schiff base for removal of cu(Ii) from aqueous solutions: A combined experimental and theoretical study

Removal of heavy metals from drinking water sources and rivers is of strategic health importance and is essential for sustainable ecosystem development, in particular in polluted areas around the globe. In this work, new hybrid inorganic-organic material

N,O-Amino-phenolate Mg(II) and Zn(II) Schiff base complexes: Synthesis and application in ring-opening polymerization of ε-caprolactone and lactides

Solventless grinding of 2-aminophenol and the corresponding aldehyde furnished compounds 2-(pyridin-2-ylmethylene)aminophenol (L1), 2-(pyridin-4-ylmethylene)aminophenol (L2), 2-(thiophen-2-ylmethylene)aminophenol (L3) and 2-(furan-2-ylmethylene)aminopheno

Hemoglobin: A New Biocatalyst for the Synthesis of 2-substituted Benzoxazoles via Oxidative Cyclization

Efficient and mild synthesis of a series of 2-substituted benzoxazoles via oxidative cyclization catalyzed by hemoglobins reported here for the first time. Satisfactory yields (84 %–97 %) and mild reaction conditions make this method highly viable for practical applications.

Enantioselective Strecker and Allylation Reactions with Aldimines Catalyzed by Chiral Oxazaborolidinium Ions

Chiral oxazaborolidinium ion (COBI)-catalyzed enantioselective nucleophilic addition reactions of aldimines using tributyltin cyanide and allyltributylstannane have been developed. Various α-aminonitriles and homoallylic amines were synthesized in high yi

OMS-2/H2O2/Dimethyl Carbonate: An Environmentally-Friendly Heterogeneous Catalytic System for the Oxidative Synthesis of Benzoxazoles at Room Temperature

A manganese octahedral molecular sieve (OMS-2) was found to be an efficient and recyclable heterogeneous catalyst for the oxidative synthesis of benzoxazoles in the gram-scale from phenolic imines at room temperature. H2O2 and biobased reagent dimethyl carbonate (DMC) were successfully employed as the environmentally friendly oxidant and solvent, respectively, in an OMS-2-catalysted redox reaction for the first time. Benzoxazoles could also be obtained from N-substituted 2-aminophenols via Cu(OH)x/OMS-2-catalyzed sequential oxidative transformation at elevated temperatures.

Sustainable Synthesis of 2-Arylbenzoxazoles over a cobalt-based nanocomposite catalyst

A new cobalt-based heterogeneous catalyst was prepared by adsorbing in situ produced nitrogen-ligated cobalt(II) acetate complexes on commercially available SiO2 and subsequent pyrolysis at 800 °C for 2 h under N2 atmosphere. By applying this catalyst under the O2 balloon, the aerobic oxidation of phenolic imines proceeded smoothly and gave various 2-arylbenzoxazoles in good yields. Meanwhile, on the basis of the experimental results, a plausible reaction pathway was described to elucidate the reaction mechanism.

General synthetic approach towards annelated 3a,6-epoxyisoindoles by tandem acylation/IMDAF reaction of furylazaheterocycles. Scope and limitations

An efficient and versatile one-pot synthesis of 3,6a-epoxyisoindoles annelated with oxazine, oxazole, thiazine, thiazole, pyrimidine fragments and with their benzoannelated analogues is presented. The method is based on tandem N-acylation/intramolecular cycloaddition (the intramolecular Diels-Alder reaction of furan, IMDAF) reaction between α,β-unsaturated acid anhydrides and α-furyl substituted azaheterocycles. The latter can be easily prepared by condensation of diverse furfurals and 1,2- or 1,3-N,X-binucleophiles (aminoalcohols, aminothiols, diamines). The observed IMDAF reaction is stereoselective: exo-adducts are formed exclusively with large prevalence of one of the diastereoisomers. In most cases, the condensation/N-acylation/IMDAF reaction sequence may be carried out via a one-pot domino protocol. The scope and limitations of the proposed approach are thoroughly investigated. The obtained Diels-Alder adducts are attractive and useful substrates for further transformations. Fused isoindoles can be prepared from them in one-step by aromatization of the 7-oxabicyclo[2.2.1]heptene ring. Other transformations, including halogenation, ring cleavage, and Wagner-Meerwein skeletal rearrangement, are also demonstrated. The spatial structures of the obtained compounds have been established by X-ray diffraction analyses.

Comparison of chelating ability of NO-, NS-, ONS-, and ONO-type Schiff base derivatives and their stability constants of Bis-complexes with copper(II)

The present study includes important findings relating to the number of donor atoms, species of ligands, and stabilities of complexes. Stabilities of complexes between Cu(II) ion and NO-, NS-, ONS-, and ONO-type Schiff bases were compared. Acid-base properties of the Schiff bases were explained at 25 ± 0.1 ° C and ionic strength (I) of 0.1 M supported by NaCl. The Hyperquad computer program was used for calculation of dissociation and stability constants. The overall stability constants of their Cu(II) complexes were calculated and the various formed complexes between the Schiff bases with Cu(II) ion formulated as CuL2, CuHL2, CuH2L 2, and CuH-1L2(Cu (OH) L2). The complexes of ONS- and ONO-type tridentate ligands were more stable than those of NO- and NS-type bidentate ligands. TUeBITAK.

Cyanide as a powerful catalyst for facile synthesis of benzofused heteroaromatic compounds via aerobic oxidation

Highly efficient synthesis of benzofused heteroaromatic compounds via aerobic oxidation catalyzed by cyanide anion has been developed. The Schiff bases derived from 2-aminophenol and aldehydes provided the corresponding benzoxazoles in high yields in the presence of a catalytic amount of cyanide in an open flask under ambient conditions without the use of any external metal co-oxidants and bases. Furthermore, we have developed a catalytic sequential one-step protocol for the synthesis of benzoxazoles by adding a catalytic amount of NaCN to Schiff bases generated in situ from 2-aminophenol and aldehydes without the isolation of imine intermediates. This one-pot protocol was further extended to the synthesis of benzothiazoles from 2-aminothiophenol and aldehydes. A variety of aldehydes could be applied to this sequential one-pot protocol and the desired benzofused azole products were obtained in high yields.