111861-25-7

Basic information

• Product Name: 4H-1-Benzopyran-3-carbonitrile, 2-amino-7-hydroxy-4-phenyl-
• CAS NO: 111861-25-7
• Molecular Formula: C16H12N2O2
• Molecular Weight: 264.283
• Mol File: 111861-25-7.mol
• Article Data: 80

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-3-carbonitrile, 2-amino-7-hydroxy-4-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-3-carbonitrile, 2-amino-7-hydroxy-4-phenyl-(111861-25-7)
• EPA Substance Registry System: 4H-1-Benzopyran-3-carbonitrile, 2-amino-7-hydroxy-4-phenyl-(111861-25-7)

Safety Data

• Hazardous Substances Data: 111861-25-7(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 109-77-3 malononitrile 
• 108-46-3 recorcinol 
• 2700-22-3 Benzylidenemalononitrile 
• 95-01-2 2,4-Dihydroxybenzaldehyde 

Downstream Products

• 1427317-69-8 C₂₀H₁₄O₃ 
• 1427317-64-3 C₂₃H₁₇BrN₂O₂ 
• 1255790-66-9 8-hydroxy-5-phenyl-3,5-dihydro-4H-chromeno[2,3-d]pyrpyrimidin-4-one 

Relevant articles and documents

Preparation of neutral ionic liquid [2-Eim] OAc with dual catalytic-solvent system roles for the synthesis of 2-amino-3-cyano-7-hydroxy-4-(aryl)-4H-chromene derivatives

A novel ionic liquid namely 2-ethyl imidazolium acetate, [2-Eim] OAc, was synthesized, and characterized by studying its FT-IR, 1H and 13C NMR, UV, thermal gravimetric analysis (TGA), differential thermal analysis (DTA) diagrams, and

A new triazine-thiophene based porous organic polymer as efficient catalyst for the synthesis of chromenes via multicomponent coupling and catalyst support for facile synthesis of HMF from carbohydrates

Functionalized porous organic polymers are very demanding and promising material in heterogeneous catalysis due to their convenience in synthesis and versatility in framework composition. Further, owing to the tunable porosity, high specific surface area,

A green method synthesis and antimicrobial activity of 2-amino-4H-chromene derivatives

Agro-waste stuff ash extracted solution have been emerging in recent practicing green reaction catalysis in organic synthesis. The derived media have been demonstrated in reactions like Sonogashira, Dakin, Henry, Suzuki-Miyaura, amide bond formation. Trad

DABCO entrapped in agar-agar: A heterogeneous gelly catalyst for multi-component synthesis of 2-amino-4H-chromenes

An efficient method for the multi-component synthesis of 2-amino-4H-chromenes by reaction of malononitrile with various aldehydes and phenols in the presence of gel entrapped DABCO as catalyst is reported.

Synthesis and characterization of a novel Fe3O4@SiO2-BenzIm-Fc[Cl]/BiOCl nano-composite and its efficient catalytic activity in the ultrasound-assisted synthesis of diverse chromene analogs

In this study, a novel magnetically recoverable Fe3O4@SiO2-BenzIm-Fc[Cl]/BiOCl nano-composite was synthesized using a simple chemical co-precipitation method. This is the first time that a magnetic nano-catalyst bearing ionic liquid, ferrocene and BiOCl is synthesized. The Fe3O4@SiO2-BenzIm-Fc[Cl]/BiOCl nano-composite was characterized by Fourier-transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), energy-dispersive X-ray spectroscopy (EDX) and field emission scanning electron microscopy (FE-SEM) techniques. The catalytic activities of the novel magnetic nano-composite were evaluated in one-pot three-component synthesis of a wide variety of 2-amino-3-cyano-4H-chromene derivatives under ultrasound irradiation. A simple, facile and highly efficient ultrasound-assisted method was developed to synthesize 4H-chromene derivatives via one-pot, three-component reaction of aldehyde, malononitrile and active phenolic compounds (2-naphthol, 1-naphthol, 3-(dimethylamino)phenol, resorcinol and orcinol) at room temperature. The reaction of aldehyde, malononitrile and orcinol is newly introduced in this paper. The ultrasound-assisted synthesis protocol that was studied in this article exhibits some notable advantages such as short reaction times, operational simplicity, green reaction conditions, high yields and easy work-up and purification steps. In addition, the novel magnetic nano-composite could be easily recovered by an external magnetic field and reused for six-reaction cycles without significant loss of its catalytic activity.

Critical assessment of the efficiency of chitosan biohydrogel beads as recyclable and heterogeneous organocatalyst for C-C bond formation

The effectiveness of neutral pH chitosan hydrogel beads (CSHB) as a green organocatalyst for a variety of C-C bond forming reactions (i.e. aldol reaction, Knoevenagel condensation, nitroaldol (Henry) reaction, Michael addition) has been comprehensively evaluated. Reaction rates, conversions and selectivities were studied as a function of a series of input variables including size, pH and reactive surface area of the beads, catalyst loading, temperature, molecular weight of the biopolymer, concentration, solvent system and molar ratio of reactants. Moreover, the catalytic biohydrogel beads were characterized by a variety of techniques including, among others, SEM, FT-IR, TGA and DSC.

Synthesis and structure of some substituted 2-amino-4-aryl-7-propargyloxy-4H-chromene-3-carbonitriles

A series of 2-amino-7-hydroxy-4H-chromene-3-carbonitriles 4a–l were synthesized through three-component reaction using sodium carbonate as a catalyst. The reaction was carried out in 96% ethanol-water medium (1:20 ratio in volume). Propargyl ether compounds 5a–l of these chromene-3-carbonitriles were successfully synthesized from corresponding hydroxyl chromene derivatives by reaction with propargyl bromide. Two different procedures were applied in this process: the procedure that used potassium carbonate in dried acetone and the procedure that used sodium hydride in dried DMF. The latter gave the ethers 5a–l in higher yields. The single-crystal X-ray structure of propargyl ether 5g has been recorded.

Nano CuO–Ag-catalyzed synthesis of some novel pyrano[2,3-d] pyrimidine derivatives and evaluation of their bioactivity

A simple, highly efficient, and green method is developed for the synthesis of pyrano[2,3-d] pyrimidine derivatives via Knoevenagel and Michael addition in the presence of nano CuO–Ag as a catalyst. The structures of synthesized target compounds 5a–l were confirmed by spectral and elemental analysis and were screened for their antioxidant activity by 2,2-diphenyl-1-picrylhydrazyl (DPPH), H2O2, and NO methods. Their antibacterial activity against Gram-negative bacteria Pseudomonas aeruginosa and Escherichia coli, against Gram-positive bacteria such as Bacillus subtilis and Staphylococcus aureus, and antifungal activity against Candida albicans and Candida glabrata was also evaluated. The compounds showed higher bacterial activity than the standard used. Compounds 5b, 5d, 5g, 5h, and 5i exhibited higher free radical scavenging activity than the standard butylated hydroxy toluene (BHT). Compounds 5b, 5d, and 5h showed higher activity on Gram-positive bacteria, and compounds 5b, 5d, 5h, and 5i showed higher activity on Gram-negative bacteria than that of standard tetracycline. Compounds 5b, 5j, and 5l showed much higher antifungal activity against Candida globrata and C. albicans than that of standard Griseofulvin.

Green synthesis of 2-amino-7-hydroxy-4-aryl-4H-chromene-3-carbonitriles using ZnO nanoparticles prepared with mulberry leaf extract and ZnCl2

A highly efficient and environmentally benign protocol for the synthesis of 2-amino-7-hydroxy-4-aryl-4H- chromene-3-carbonitrile derivatives in good to high yields (77%{97%) by one-pot three-component coupling reaction of aromatic aldehydes, malononitrile

Ultrasonic activated efficient synthesis of chromenes using amino-silane modified Fe3O4 nanoparticles: A versatile integration of high catalytic activity and facile recovery

An efficient synthesis of 2-amino-4H-chromenes is achieved by one pot three component coupling reaction of aldehyde, malononitrile, and resorcinol using amino-silane modified Fe3O4 nanoparticles (MNPs-NH 2) heterogeneous nanocatalyst under sonic condition. The attractive advantages of the present process are mild reaction conditions, short reaction times, easy isolation of products, good yields and simple operational procedures. Combination of the advantages of ultrasonic irradiation and magnetic nanoparticles provides important methodology to carry out catalytic transformations.

The amino side chains do matter: Chemoselectivity in the one-pot three-component synthesis of 2-amino-4: H -chromenes by supramolecular catalysis with amino-appended β-cyclodextrins (ACDs) in water

In this study, the one-pot three-component synthesis of 2-amino-4H-chromenes was accomplished by supramolecular catalysis using a series of well-designed amino-appended β-cyclodextrins (ACDs) in water. The catalytic mechanism was elucidated in detail with 1D and 2D NMR and ESI-MS analyses, while the key roles of amino side chains of ACDs in the reaction chemoselectivity were addressed for the first time.

A multi-component electro-organic synthesis of 2-amino-4H-chromenes

Electrochemically induced multi-component condensation of resorcinol, malononitrile, and various aldehydes in propanol in an undivided cell in the presence of NaBr as an electrolyte results in the formation of 2-amino-4H-chromenes in good yields and short reaction time.

Synthesis and biological evaluation of new chromenes and chromeno[2,3-d] pyrimidines

A simple and efficient approach has been developed to synthesise novel and functionalised 5H-chromeno[2,3-d] pyrimidines derivatives (4a-h). This approach entails treating 2-amino-3-cyano-4H-chromenes (3a-h) with formamidine acetate under microwave irradi

Three-component coupling approach for the synthesis of 4H-pyrans and pyran-annulated heterocyclic scaffolds utilizing Ag/TiO2 nano-thin films as robust recoverable catalyst

As a segment of ongoing surveys and with the aim of expansion of environmentally benign processes, a series of biologically varied type of substituted 2-amino-3-cyano-4H-pyrans and pyran-annulated Scaffolds have been synthesized by tandem Knoevenagel-cycl