144464-54-0

Basic information

• Product Name: 2-AMINO-4-(4-METHYLPHENYL)-4H-BENZO[H]CHROMENE-3-CARBONITRILE
• Synonyms: 2-AMINO-4-(4-METHYLPHENYL)-4H-BENZO[H]CHROMENE-3-CARBONITRILE
• CAS NO: 144464-54-0
• Molecular Formula: C₂₁H₁₆N₂O
• Molecular Weight: 312.36
• Mol File: 144464-54-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-AMINO-4-(4-METHYLPHENYL)-4H-BENZO[H]CHROMENE-3-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-4-(4-METHYLPHENYL)-4H-BENZO[H]CHROMENE-3-CARBONITRILE(144464-54-0)
• EPA Substance Registry System: 2-AMINO-4-(4-METHYLPHENYL)-4H-BENZO[H]CHROMENE-3-CARBONITRILE(144464-54-0)

Safety Data

• Hazardous Substances Data: 144464-54-0(Hazardous Substances Data)

Usage

Chemical compound

2-AMINO-4-(4-METHYLPHENYL)-4H-BENZO[H]CHROMENE-3-CARBONITRILE

Class

Benzo[h]chromene derivatives

Structure

Benzo[h]chromene core substituted with an amino group, a 4-methylphenyl group, and a carbonitrile group at the 3-position

Biological activities

Potential biological activities

Application

Medicinal chemistry and drug discovery research

Value

Valuable scaffold for the development of novel pharmaceutical compounds

Therapeutic applications

Particularly in the treatment of cancer, inflammation, and neurological disorders

Upstream product

• 90-15-3 α-naphthol 
• 2826-25-7 2-(4-methylbenzylidene)malononitrile 
• 104-87-0 4-methyl-benzaldehyde 
• 109-77-3 malononitrile 
• 589-18-4 4-Methylbenzyl alcohol 

Downstream Products

• 1393816-51-7 7-(p-tolyl)-9,10,11,12-tetrahydro-7H-benzo[7,8]chromeno[2,3-b]quinolin-8-amine 
• 1446242-91-6 2-oxo-4-p-tolyl-2H-benzo[h]chromene-3-carbonitrile 
• 1621314-74-6 10-chloromethyl-7-(p-methylphenyl)-7,9-dihydrobenzo[7,8]chromeno[2,3-d]pyrimidin-8-one 
• 1621314-58-6 2-chloro-N-(3-cyano-4-(p-methylphenyl)-4H-benzo[h]chromen-2-yl)acetamide 
• 1414397-81-1 C₂₂H₁₉ClN₂O₂ 
• 1613306-66-3 dimethyl 3-(4-methylphenyl)naphtho[1,2-b]furan-2,2(3H)-bis(carbimidate) 
• 1613306-52-7 methyl 2-cyano-3-(4-methylphenyl)-2,3-dihydronaphtho[1,2-b]furan-2-carbimidate 
• 1259371-49-7 10-methyl-7-(4-methylphenyl)-8,9-dihydro-7H-12-oxa-9,11-diaza-benzo[a]anthracene-8-one 
• 144464-58-4 8-Amino-10-methyl-7-p-tolyl-7H-12-oxa-11-aza-benzo[a]anthracene-9-carbonitrile 

Relevant articles and documents

Solvent Selective Polyacrylonitrile Fiber as a Recyclable Catalyst for the Knoevenagel-Michael Reaction in Water

Heterogeneous catalysis is an important branch of sustainable chemistry. In this work, a series of polyacrylonitrile fiber (PANF) fiber catalysts (PANF-E, PANF-EDs, and PANF-D) with different catalytic micro-environments are developed and characterized by

Choline chloride-coated UiO-66-Urea MOF: A novel multifunctional heterogeneous catalyst for efficient one-pot three-component synthesis of 2-amino-4H-chromenes

A new Zr-based MOF, namely, UiO-66-Urea, was prepared through polymerization between the 2-aminoterephthalate linkers of UiO-66-NH2 MOF and 1,4-phenylene diisocyanate under mild reaction conditions. Post-synthetic coating of UiO-66-Urea with ch

Bipyridinium chloride supported rice husk silica: An efficient nanocomposite for the one-pot preparation of spirooxindole pyran and 2-amino-4h-chromene derivatives

In this paper, rice-husk-silica supported n-propyl bipyridinium chloride (RHPrBPCl) has been prepared as a heterogeneous catalyst. RHPrBPCl has been successfully applied in the one-pot preparation of spirooxindole pyran and 2-amino- 4H-chromene derivative

Biocompatible Ionic Liquid Promote One-Pot Synthesis of 2-Amino-4H-Chromenes Under Ambient Conditions

Abstract: The synthesis of 2-amino-4H-chromenes through one-pot multicomponent reactions has received great attention due to the high atom efficiency and the broad bioactivities of the products. Here, the catalytic performances of a series of functional ionic liquids towards this type of reaction were investigated and the results showed that the ionic liquid, choline acetate ([Choline][Ac]), could efficiently promote this reactions under room temperature without the necessary of organic solvents. The reaction is easy to be conducted and the following work-up procedures are very simple. The pure products can be obtained through extraction and washing procedures, no column separation procedures are needed. Intriguingly, this reaction system can be easily scaled up to multi-gram, suggesting its perspective in industrial applications. In addition, the ionic liquid [Choline][Ac] can be easily prepared from cheap and biocompatible materials, and it can be feasibly recycled and reutilized for at least five cycles. Graphic Abstract: Various aldehydes, malononitrile and activated phenols could be converted to thecorresponding 2-amino-4H-chromenes with good to excellent isolated yields underthe catalysis of choline acetate at room temperature. [Figure not available: see fulltext.]

One-pot Synthesis of 2-Amino-4H-Chromenes using Chicken Eggshell Waste as Green Catalyst under Solvent-Free Conditions

Chicken eggshell waste has been employed as green and efficient catalyst for the preparation of 2-amino-4H-chromenes. The aromatic aldehydes were condensed with malononitrile and 1-naphthol or 2-naphthol under solvent-free condition in the presence of chi

Organocatalytic Cascade Knoevenagel–Michael Addition Reactions: Direct Synthesis of Polysubstituted 2-Amino-4H-Chromene Derivatives

Abstract: In this report, we documented novel strategy for the synthesis of bioactive polysubstituted 2-amino-4H-chromine derivatives under a heterogeneous Al-MCM-41-LDH@APTES (ALAM) catalysis. A synthetic procedure is developed to prepare Al-MCM-41-LDH@APTES (ALAM) heterogeneous basic catalysts. Mesoporous Al-MCM-41 is functionalized by known grafting chemistry via layered double hydroxide (LDH) nanosheets and (3-aminopropyl)triethoxysilane (APTES) moiety as a basic organocatalyst. The resulting catalysts contain amino group functionality on the external surface as well as inside the layers and the basicity can be tuned by the loading of APTES. The samples were fully characterized by 29Si and 13C CP/MAS NMR, infrared absorption spectroscopy, TEM, XPS, EDX, TGA, XRD, CO2-TPD, N2 adsorption isotherms measurements, and they were successfully examined for the cascade type Knoevenagel–Michael addition reactions. The product yields associated with these substrates were optimized, and key reaction parameters affecting the yields were identified. The present catalytic method is simple and robust for diversity oriented synthesis which proceeds good to excellent yields without generating any hazards waste. The broad substrate scope, excellent functional group compatibility makes this protocol highly useful towards synthesis of polysubstituted α-cyanoacrylates, α-cyanoacrylonitriles and 2-amino-4H-chromenes with an electron-donating or electron-withdrawing group. We have also successfully established a flow reaction system, gram-scale synthesis as well as catalyst recyclability up to six catalytic cycles without appreciable loss of its activity. Graphic Abstract: [Figure not available: see fulltext.].

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.

Triethanolamine-catalyzed expeditious and greener synthesis of 2-amino-4H-chromenes

Triethanolamine (TEOA), an inexpensive and eco-friendly base, was used to efficiently catalyze the three-component condensation reaction of heterocyclic/aromatic aldehyde, (α/β)-naphthol, and malononitrile in water to give the corresponding substituted 2-

Bipyridinium chloride supported rice husk silica: An efficient nanocomposite for the one-pot preparation of spirooxindole pyran and 2-amino-4H-chromene derivatives

In this paper, rice-husk-silica supported n-propyl bipyridinium chloride (RHPrBPCl) has been prepared as a heterogeneous catalyst. RHPrBPCl has been successfully applied in the one-pot preparation of spirooxindole pyran and 2-amino-4H-chromene derivatives

Novel task-specific ionic liquid [Et2NH(CH2)2CO2H][AcO] as a robust catalyst for the efficient synthesis of some pyran-annulated scaffolds under solvent-free conditions

A novel task-specific ionic liquid, 2-carboxy-N,N-diethylethanaminium acetate denoted as [Et2NH(CH2)2CO2H][AcO], is prepared in an easy process and fully characterized by using suitable methods such as FT-IR, 1H-NMR, 13C-NMR, and TG, DTG and DTA analyses. After preparation, the promoting ability of this catalyst for one-pot multicomponent synthesis of 2-amino-4H-chromenes, dihydropyrano[3,2-c]chromenes and dihydropyrano[2,3-c]pyrazoles using in situ-developed arylidenemalononitriles through Knoevenagel reaction under solvent-free conditions is described. The sustainable procedure, short reaction times (6–36?min), effortless work-up, non-chromatographic purification, good-to-excellent product yields (79–96%), ease of recovery and reusability of the catalyst up to six reaction runs without a decrease of activity are the notable features of the present protocol.