18931-79-8

Basic information

• Product Name: N-(2-chloro-4-methylphenyl)pivalamide
• Synonyms: N-(2-chloro-4-methylphenyl)pivalamide
• CAS NO: 18931-79-8
• Molecular Weight: 225.718
• Mol File: 18931-79-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: N-(2-chloro-4-methylphenyl)pivalamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-chloro-4-methylphenyl)pivalamide(18931-79-8)
• EPA Substance Registry System: N-(2-chloro-4-methylphenyl)pivalamide(18931-79-8)

Safety Data

• Hazardous Substances Data: 18931-79-8(Hazardous Substances Data)

Upstream product

• 21354-40-5 2,2-dimethyl-N-(4-methylphenyl)propanamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 106-49-0 p-toluidine 
• 3282-30-2 pivaloyl chloride 

Downstream Products

• 1245795-71-4 ethyl 3-chloro-5-methyl-2-(pivalamido)phenylcarbamate 

Relevant articles and documents

Palladium-catalyzed regio- and chemoselective direct desulfitative arylation of anilides with arylsulfonyl chlorides

A straightforward and practical palladium-catalyzed regioselective arylation of anilides is described. This method provides a new approach to prepare 2-aminobiaryls, which are valuable precursors for the synthesis of various N-containing heterocycles, using arylsulfonyl chlorides as readily available arylating agents.

Amide-assisted radical strategy: Metal-free direct fluorination of arenes in aqueous media

A metal- and initiator-free direct fluorination of arenes with the assistance of an amide group is developed. This reaction proceeded under simple aqueous conditions with good functional group tolerance and ortho-para selectivity, and is highly practical because it could be readily scaled up to a multigram-scale. At this stage, an exclusive mechanism could not be proposed, and several possibilities have been discussed. The possibility of the amide-assisted radical chain mechanism has been supported by experimental and computational investigations as well as a seminal work.

Solvent-free aromatic C-H functionalisation/halogenation reactions

The solvent-free, palladium-catalysed reaction of anilides with CuCl 2 in the presence or absence of copper acetate yields ortho-chlorinated anilides in good to excellent yields, even on a large scale (100 mmol). By contrast, the equivalent reactions with copper bromide, either solvent free or in 1,2-dichloroethane, in the presence or absence of palladium, under air or inert conditions, gave the products of simple electrophilic bromination. Mechanistic studies highlighted the involvement of palladacyclic intermediates, one of which was characterised crystallographically, which undergo subsequent reaction with copper(ii) chloride to yield the chlorinated anilide products.