149550-68-5

Basic information

• Product Name: 2-AMINO-4-(3,4-DIMETHOXYPHENYL)-4H-BENZO[H]CHROMENE-3-CARBONITRILE
• Synonyms: 2-AMINO-4-(3,4-DIMETHOXYPHENYL)-4H-BENZO[H]CHROMENE-3-CARBONITRILE
• CAS NO: 149550-68-5
• Molecular Formula: C22H18N2O3
• Molecular Weight: 358.39
• Mol File: 149550-68-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-AMINO-4-(3,4-DIMETHOXYPHENYL)-4H-BENZO[H]CHROMENE-3-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-4-(3,4-DIMETHOXYPHENYL)-4H-BENZO[H]CHROMENE-3-CARBONITRILE(149550-68-5)
• EPA Substance Registry System: 2-AMINO-4-(3,4-DIMETHOXYPHENYL)-4H-BENZO[H]CHROMENE-3-CARBONITRILE(149550-68-5)

Safety Data

• Hazardous Substances Data: 149550-68-5(Hazardous Substances Data)

Usage

Classification

Benzo[h]chromene derivative

Functional groups

Amino group, two methoxy groups

Potential applications

Pharmaceutical and chemical research

Use

Development of new drugs, probe in biological studies

Unique properties

Complex structure, potential biological activity, interesting candidate for further investigation

Upstream product

• 90-15-3 α-naphthol 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 109-77-3 malononitrile 

Downstream Products

• 845649-71-0 C₂₅H₂₃N₃O₃ 
• 1446242-90-5 4-(3,4-dimethoxyphenyl)-2-oxo-2H-benzo[h]chromene-3-carbonitrile 

Relevant articles and documents

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.].

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