61131-68-8

Basic information

• Product Name: 4-chloro-2-[(E)-2-nitroethenyl]phenol
• Synonyms: Phenol, 4-chloro-2-(2-nitroethenyl)-
• CAS NO: 61131-68-8
• Molecular Formula: C₈H₆ClNO₃
• Molecular Weight: 199.5911
• Mol File: 61131-68-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 361.6°C at 760 mmHg
• Flash Point: 172.5°C
• Density: 1.456g/cm³
• Vapor Pressure: 9.87E-06mmHg at 25°C
• Refractive Index: 1.655
• CAS DataBase Reference: 4-chloro-2-[(E)-2-nitroethenyl]phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-2-[(E)-2-nitroethenyl]phenol(61131-68-8)
• EPA Substance Registry System: 4-chloro-2-[(E)-2-nitroethenyl]phenol(61131-68-8)

Safety Data

• Hazardous Substances Data: 61131-68-8(Hazardous Substances Data)

Upstream product

• 75-52-5 nitromethane 
• 635-93-8 5-chlorosalicyclaldehyde 

Downstream Products

• 16634-90-5 2-hydroxy-3-nitro-5-chlorobenzaldehyde 
• 82842-89-5 (4-Chloro-phenyl)-carbamic acid 4-chloro-2-((Z)-2-nitro-vinyl)-phenyl ester 
• 82842-94-2 Naphthalen-1-yl-carbamic acid 4-chloro-2-((Z)-2-nitro-vinyl)-phenyl ester 
• 1220194-03-5 (R)-6-chloro-4-nitromethyl-2-phenyl-4H-chromene-3-carbaldehyde 
• 1220194-13-7 (R)-6-chloro-4-nitromethyl-2-p-tolyl-4H-chromene-3-carbaldehyde 
• 1301745-51-6 (1R,2S)-4-chloro-2-(3-hydroxy-2-methyl-1-nitromethylpropyl)phenol 
• 30335-66-1 nitro-2 chloro-5 benzofuranne 

Relevant articles and documents

Regio- and Stereoselective Cascade of β,γ-Unsaturated Ketones by Dipeptided Phosphonium Salt Catalysis: Stereospecific Construction of Dihydrofuro-Fused [2,3-b] Skeletons

Chiral (dihydro)furo-fused heterocycles are significant structural motifs in numerous natural products, functional materials and pharmaceuticals. Therefore, developing efficient methods for preparing compounds with these privileged scaffolds is an important endeavor in synthetic chemistry. Herein, we develop an effective, modular method by a dipeptide-phosphonium salt-catalyzed regio- and stereoselective cascade reaction of readily available linear β,γ-unsaturated ketones with aromatic alkenes, affording a wide variety of structurally fused heterocyclic molecules in high yields with excellent stereoselectivities. Moreover, mechanistic investigations revealed that the bifunctional phosphonium salt controlled the regio- and stereoselectivities of this cascade reaction, particularly proceeding through the initial ketone α-addition followed by O-participated substitution; and the multiple hydrogen-bonding interactions between Br?nsted acid moieties of catalyst and nitro group of aromatic alkene were crucial in asymmetric induction. Given the generality, versatility, and high efficiency of this method, we anticipate that it will have broad synthetic utilities.

Facile synthesis of chiral [2,3]-fused hydrobenzofuran: Via asymmetric Cu(i)-catalyzed dearomative 1,3-dipolar cycloaddition

Intermolecular asymmetric dearomative 1,3-dipolar cycloaddition of 2-nitrobenzofurans with azomethine ylides was enabled by using a chiral Cu(i)/(S,Sp)-iPr-Phosferrox catalyst. As a result, a series of highly stereoselective chiral [2,3]-fused hydrobenzofurans possessing four contiguous stereogenic centers were obtained with good to high yields, diastereoselectivities and enantioselectivities. The reaction has broad substrate scope tolerating various functional groups.

Organocatalytic Enantioselective Michael-Acetalization-Henry Reaction Cascade of 2-Hydroxynitrostyrene and 5-Oxohexanal for the Entry to the Hexahydro-6H-benzo[c]chromenones with Four Consecutive Stereogenic Centers and an Approach to Aflatoxin Analogues

A domino reaction with the organocatalytic enantioselective Michael-acetalization-Henry reaction of 2-hydroxynitrostyrene and 5-oxohexanal was developed for the synthesis of hexahydro-6H-benzo[c]chromenones with four consecutive stereogenic centers and high enantioselectivity (up to >99% ee). The transformation of a NaBH4-reduced adduct to the aflatoxin system via the Nef-cyclization process was achieved by the assistant of ZnBr2.