5281-22-1

Upstream product

• 67-66-3 chloroform 
• 555-16-8 4-nitrobenzaldehdye 
• 2201-11-8 1,1,1-trichloro-2-(4-nitrophenyl)-ethane 
• 56-23-5 tetrachloromethane 
• 175921-95-6 (E)-1-(4-nitrobenzylidene)hydrazine 
• 1620143-51-2 ethyl [2,2,2-trichloro-1-(4-nitrophenyl)ethyl]carbonate 
• 54075-25-1 4-nitro-α-(trichloromethyl)benzyl alcohol 
• 75-62-7 Bromotrichloromethane 
• 6310-10-7 4-nitrobenzaldehyde hydrazone 
• 100-05-0 4-nitrobenzenediazonium chloride 
• 100-01-6 4-nitro-aniline 

Downstream Products

• 20264-91-9 1-(chloroethynyl)-4-nitrobenzene 
• 1353724-94-3 ethyl 1-chloro-2-(4-nitrophenyl)indolizine-3-carboxylate 
• 1353724-96-5 1-chloro-2-(4-nitrophenyl)indolizine-3-carbonitrile 
• 15852-01-4 1-chloro-4-[(4-nitrophenyl)ethynyl]benzene 
• 64583-21-7 1-fluoro-4-(2-(4-nitrophenyl)ethynyl)benzene 
• 1942-30-9 4-(phenylethynyl)nitrobenzene 
• 126521-89-9 1,3-benzothiazol-2-yl(4-nitrophenyl)methanone 
• 1367843-31-9 4-chloro-3-(4-nitrophenyl)-1-phenyl-1H-pyrazole 
• 1370287-78-7 4-chloro-1-(4-methoxyphenyl)-3-(4-nitrophenyl)-5-phenyl-1H-pyrazole 
• 1370287-77-6 4-chloro-3-(4-nitrophenyl)-1,5-diphenyl-1H-pyrazole 
• 1367843-35-3 4-chloro-3-(4-nitrophenyl)-1-p-tolyl-1H-pyrazole 
• 1367843-41-1 4-chloro-1-(4-methoxyphenyl)-3-(4-nitrophenyl)-1H-pyrazole 

Relevant academic research and scientific papers

Visible-Light-Mediated Z -Stereoselective Monoalkylation of β,β-Dichlorostyrenes by Photoredox/Nickel Dual Catalysis

Metal-catalyzed alkylation of 1,1-dihalovinyl moiety commonly suffers from both a lack of stereoselectivity and the overreaction leading to the dialkylation product. The methodology described herein features a new pathway to alkylate stereoselectively β,β-dichlorostyryl substrates to provide the Z -trisubstituted olefin only with fair to good yields. This cross-coupling reaction bears on the smooth and photoinduced formation of a C-centered radical that engages in a nickel-catalyzed organometallic cycle to form the key C sp2-C sp3bond.

Cross-coupling reactivity of 1,1-dichloroalkenes under palladium catalysis: Domino synthesis of diarylalkynes

An efficient synthesis of diarylalkynes was achieved from the domino cross-coupling reaction of 1,1-dichloroalkenes with triarylbismuth reagents under palladium-catalyzed conditions. Under the established palladium protocol, 1,1-dichloroalkenes demonstrated hitherto unknown remarkable cross-coupling reactivity with organometallic triarylbismuth reagents to furnish functionalized diarylalkynes.

Ionic liquids as a reusable media for copper catalysis. Green access to alkenes using catalytic olefination reaction

It was demonstrated that ionic liquids are superb recyclable media for copper catalyzed reactions using catalytic olefination reaction as an example. As a result a novel green access to the halogenoalkenes was elaborated. Possibility to perform up to five reaction cycles without catalyst leaching and decreasing of the yield was demonstrated. A number of various ionic liquids was screened and 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim] [BF4]) was found the solvent with highest efficiency. Mild conditions, high atom economy comparing to other known methods, low amounts of wastes and possibility to recover ionic liquid are the advantages of the proposed method.

β-(Carbonatoxy)alkyl radicals: A new subset of β-(ester)alkyl radical fragmentation during copper(I)-mediated synthesis of 1,1-dichloro-1-alkenes

A new subset of β-(ester)alkyl radicals is presented. It is the first study on the chemistry of β-(alkoxycarbonyloxy)alkyl radicals that fill the gap in the spectrum of the migrating groups in β-(ester)alkyl radical reactions. The change from less nucleofugal (acetate) group to the more nucleofugal (carbonate) group in the spectrum of the migrating group changed the reaction path from rearrangement to fragmentation. This approach has been used for the synthesis of 1,1-dichloroalkenes in high yields. The formation of dichloroalkenes was accounted by the involvement of alkene radical cation and carbonate anion pair (a CIP) as a result of heterolysis of the CO bond of the carbonate at the β-position of the β-(alkoxycarbonyloxy)alkyl radical. The alkene radical cation was trapped by nucleophilic reaction with MeOH to form methyl ester.

Convenient synthesis of 2-aryl-1-haloindolizines from pyridinium salts and 2-aryl-1,1-dihaloalk-1-enes

2-Aryl-1-haloindolizines were synthesized from pyridinium salts and 2-aryl-1,1-dihaloalk-1-enes using a DBU/THF system. 2-Aryl-1,1-dihaloalk-1-enes containing electron-withdrawing or -donating groups were efficiently converted into the corresponding 2-aryl-1-haloindolizines in moderate to excellent yields. Georg Thieme Verlag Stuttgart.

Efficient synthesis of 1,3-diaryl-4-halo-1 H-pyrazoles from 3-arylsydnones and 2-aryl-1,1-dihalo-1-alkenes

An efficient synthesis of 1,3-diaryl-4-halo-1H-pyrazoles was achieved. The synthesis involves the [3 + 2] dipolar cycloaddition of 3-arylsydnones and 2-aryl-1,1-dihalo-1-alkenes. The process proceeds smoothly in moderate to excellent yields. 1,3-Diaryl-4-

The use of bromotrichloromethane in chlorination reactions

Carbon tetrachloride is no longer used as a common solvent due to its toxicity and harmful environmental impact. The synthesis of gem-dichloroalkenes from aldehydes by using triphenylphosphine typically requires carbon tetrachloride as a solvent. We report that stoichiometric bromotrichloromethane in acetonitrile can be used in place of solvent quantities of carbon tetrachloride in this transformation. Similarly, bromotrichloromethane in dichloromethane can be used for the room-temperature Appel reaction of benzyl alcohols to form benzyl chlorides, which is commonly carried out in refluxing carbon tetrachloride. Georg Thieme Verlag Stuttgart New York.

Catalytic olefination of carbonyl compounds. Effect of the structure of the carbonyl compound on the reaction

The mechanism of the novel reaction of catalytic olefination of carbonyl compounds was studied. The reaction involves the transformation of hydrazones of aromatic aldehydes and ketones into the corresponding dichloroalkenes and symmetrical azines by the treatment with carbon tetrachloride in the presence of CuCl as a catalyst. The stability of intermediate diazoalkanes is the main factor determining the direction of the reaction. In the case of sufficiently stable diazoalkanes, other products can be formed under the reaction conditions along with the products of catalytic olefination.

Conversion of aromatic aldehydes into 1-aryl-2,2-dichloroethenes

A new general one-pot preparative method for the synthesis of 1-aryl(hetaryl)-2,2-dichloroethenes from aldehydes was developed. The method involves successive conversions of the latter into hydrazones followed by treatment with carbon tetrachloride in the

A novel synthetic approach to dichlorostyrenes

We found that N-unsubstituted hydrazones of aromatic aldehydes can be easily converted to the corresponding 1,1-dichlorostyrenes in the reaction with carbon tetrachloride using copper (I) chloride as catalyst. Factors affecting the route of the reaction and yields of the products were investigated. A proposed mechanism for the reaction is discussed. (C) 2000 Published by Elsevier Science Ltd.