1451195-14-4

Basic information

• Product Name: (R)-4-[1-(4-chlorophenyl)-2-nitroethyl]-5-methyl-2-phenyl-2H-pyrazol-3-ol
• Synonyms: (R)-4-[1-(4-chlorophenyl)-2-nitroethyl]-5-methyl-2-phenyl-2H-pyrazol-3-ol
• CAS NO: 1451195-14-4
• Molecular Weight: 357.796
• Mol File: 1451195-14-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (R)-4-[1-(4-chlorophenyl)-2-nitroethyl]-5-methyl-2-phenyl-2H-pyrazol-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-[1-(4-chlorophenyl)-2-nitroethyl]-5-methyl-2-phenyl-2H-pyrazol-3-ol(1451195-14-4)
• EPA Substance Registry System: (R)-4-[1-(4-chlorophenyl)-2-nitroethyl]-5-methyl-2-phenyl-2H-pyrazol-3-ol(1451195-14-4)

Safety Data

• Hazardous Substances Data: 1451195-14-4(Hazardous Substances Data)

Upstream product

• 706-07-0 1-chloro-4-(2-nitrovinyl)benzene 
• 89-25-8 edaravone 

Downstream Products

• 1440199-46-1 4-(1-(4-chlorophenyl)-2-nitroethyl)-4-fluoro-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one 

Relevant articles and documents

Asymmetric cooperative catalysis in the conjugate addition of pyrazolones to nitroolefins and subsequent dearomative chlorination

Over the past decade many bifunctional amine-thioureas have been developed as active metal-free organocatalysts. Cooperative catalysis of these amino-thioureas allows high reaction rates and excellent transfer of stereochemical information. Despite these impressive advances, the design of new high-performance catalysts for applications in asymmetric catalytic reactions is of ongoing interest in organic chemistry. Herein we describe a cooperative catalyst system consisting of a chiral aminethiourea and an achiral organic acid that promotes the conjugate addition of 4-nonsubstituted pyrazolones to nitroolefins and subsequent dearomative chlorination. The corresponding adducts and the subsequent products were obtained in high to excellent yields (up to 99%) and high stereoselectivities (up to 99/1 dr, 98% ee) under mild reaction conditions. These transformations provide an easy access to enantio-enriched pyrazole derivatives, which could possess potential pharmaceutical activity.

Enantioselective Conjugate Addition of Pyrazolones to Nitroalkenes Catalyzed by Binaphthyl-modified Squaramide Organocatalyst

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Highly diastereo- and enantioselective organocatalytic one-pot sequential 1,4-addition/dearomative-fluorination transformation

Fluorination: A wide range of nitroolefins and pyrazol-5-ones undergo a sequential 1,4-addition/dearomative-fluorination transformation when treated with a catalytic amount of a tertiary-amine-thiourea compound and the terminal electrophile, N-fluorobenzenesulfonimide, to give fluorinated products in 72-95 % yield with up to 99:1 d.r. and 98 % ee. Notably, these products contain adjacent tertiary and α-fluoro quaternary stereocenters (see scheme). Copyright