78823-38-8

Basic information

• Product Name: p-toluic pivalic anhydride
• Synonyms: p-toluic pivalic anhydride
• CAS NO: 78823-38-8
• Molecular Weight: 220.268
• Mol File: 78823-38-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: p-toluic pivalic anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: p-toluic pivalic anhydride(78823-38-8)
• EPA Substance Registry System: p-toluic pivalic anhydride(78823-38-8)

Safety Data

• Hazardous Substances Data: 78823-38-8(Hazardous Substances Data)

Upstream product

• 3282-30-2 pivaloyl chloride 
• 99-94-5 p-Toluic acid 
• 201230-82-2 carbon monoxide 
• 459-44-9 4-methylbenzenediazonium tetrafluoroborate 
• 1184-88-9 sodium pivalate 

Downstream Products

• 111752-26-2 piperazin-1-yl(p-tolyl)methanone 
• 938-16-9 2,2-dimethylpropiophenone 
• 134-84-9 4-Methylbenzophenone 
• 2728-05-4 N,N-Diethyl-p-toluamid 

Relevant articles and documents

Synthesis of unsymmetrical ketones by palladium-catalyzed cross-coupling reaction of carboxylic anhydrides with organoboron compounds

On the basis of fundamental studies on oxidative addition of carboxylic anhydrides to zerovalent palladium complexes to yield acyl(carboxylato)bis(tertiary phosphine)palladium(II) complexes and their reactions with organoboronic acids to yield ketones, a novel catalytic process has been developed. This converts carboxylic anhydrides and organoboron compounds into ketones catalyzed by palladium complexes under mild conditions. The process provides a general, versatile, synthetic method to produce various symmetrical and unsymmetrical ketones with aromatic, aliphatic, and heterocyclic groups. The catalytic cycle is proposed to comprise (a) oxidative addition of a carboxylic anhydride to produce an acyl(carboxylato)palladium intermediate, (b) transmetallation with an organoboron compound to give an acyl(organo)palladium intermediate, and (c) its reductive elimination to yield a ketone. Not only homogeneous catalyst systems but also heterogeneous systems were found to give ketones under mild conditions.

Reaction of Diazonium Salts with Transition Metals. 6. Preparation of Mixed Acid Anhydrides from Arenediazonium Salts and Sodium Carboxylates under Palladium(0) Catalysis

The palladium(0)-catalyzed reaction of arenediazonium tetrafluoroborates with carbon monoxide and sodium carboxylates in acetonitrile at 25 deg C gave mixed acid anhydrides, ArCOOCOR (Ar = 3-Me-Ph, 4-Me-Ph, 2-MeO-Ph, 4-Br-Ph, 4-I-Ph, 3-NO2-Ph, 4-NO2-Ph, and Ph; R = H, Me, Et, t-Bu, and Ph) in good yields.Homoaromatic acid anhydrides, (ArCO)2O, were obtained by heating of ArCOOCOMe at 100-120 deg C under vacuum.ArCOOCO-t-Bu can be utilized to obtain the corresponding arenecarboxamides by the reaction with some amines.