65078-75-3

Usage

InChI:InChI=1/C8H6Cl2N2O3/c1-4(13)11-8-6(10)2-5(9)3-7(8)12(14)15/h2-3H,1H3,(H,11,13)

Upstream product

• 108-24-7 acetic anhydride 
• 2683-43-4 2,4-dichloro-6-nitroaniline 
• 552-32-9 o-nitroacetanilide 
• 88-74-4 2-nitro-aniline 
• 103-84-4 Acetanilid 
• 554-00-7 2,4-Dichloroaniline 
• 6975-29-7 N-(2,4-dichlorophenyl)acetamide 

Downstream Products

• 113001-00-6 2-amino-4,6-dichloroacetanilide 
• 113001-08-4 N-(2,4-Dichloro-6-{[1-(2-nitro-phenyl)-meth-(Z)-ylidene]-amino}-phenyl)-acetamide 
• 2683-43-4 2,4-dichloro-6-nitroaniline 

Relevant academic research and scientific papers

Activator free, expeditious and eco-friendly chlorination of activated arenes by N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI)

N-Chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI) has been explored for the first time as a chlorinating reagent for direct chlorination of various activated arenes and heterocycles without any activator. A comparative in-silico study was performed to determine the electrophilic character for NCBSI and commercially available N-chloro reagents to reveal the reactivity on a theoretical viewpoint. The reagent was prepared by an improved method avoiding the use of hazardous t-butyl hypochlorite. This reagent was proved to be very reactive compared to other N-chloro reagents. The precursor of the reagent N-(phenylsulfonyl)benzene sulfonamide was recovered from aqueous spent, which can be recycled to synthesize NCBSI. The eco-friendly protocol was equally applicable for the synthesis of industrially important chloroxylenol as an antibacterial agent.

Regioselective ortho-nitration of N-phenyl carboxamides and primary anilines using bismuth nitrate/acetic anhydride

An efficient and one-pot synthetic method for the regioselective ortho-nitration of the N-phenyl carboxamides and primary anilines has been developed by using bismuth nitrate and acetic anhydride as the nitrating reagents. Reaction proceeds at room temperature and results in corresponding ortho-nitrated products in moderate to excellent yields. This method provides an operationally simple, regioselective, and efficient access to synthesize o-nitro anilines under the mild conditions.

The electrophilic substitution of some 2,4- and 2,6- dihaloacetanilides

The orientation of electrophilic substitution of some 2,4- and 2,6-dihaloacetanilides has been examined by NMR methods. Mixed acid nitration of 2,6-dichloro and 2-chloro-6-methylacetanilides gave predominantly the 3-nitro derivatives.