136708-00-4

Basic information

• Product Name: α-tert-butyl-p-methylbenzyl acetate
• CAS NO: 136708-00-4
• Molecular Weight: 220.312
• Mol File: 136708-00-4.mol

Chemical Properties

• CAS DataBase Reference: α-tert-butyl-p-methylbenzyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: α-tert-butyl-p-methylbenzyl acetate(136708-00-4)
• EPA Substance Registry System: α-tert-butyl-p-methylbenzyl acetate(136708-00-4)

Safety Data

• Hazardous Substances Data: 136708-00-4(Hazardous Substances Data)

Upstream product

• 24797-40-8 4-methyl-1-(2,2-dimethylpropyl)benzene 
• 64-19-7 acetic acid 
• 30314-44-4 2,2-dimethyl-1-(4-methylphenyl)-1-propanone 
• 6013-94-1 2,2-dimethyl-1-(4-methylphenyl)propan-1-ol 
• 108-24-7 acetic anhydride 

Relevant articles and documents

Anodic Oxidation of α-Substituted p-Xylenes. Electronic and Stereoelectronic Effects of α-Substituents in the Deprotonation of Alkylaromatic Radical Cations

The effect of α-substituents on the deprotonation rate from the benzylic position of alkylaromatic radical cations, k(CH2Z)/k(CH3), has been investigated by determining the intramolecular selectivity in the anodic oxidation in acetic acid of a α-Z-substituted p-xylenes 1 (Z = H, OMe, OH, Me, tert-butyl, OAc, COOMe, CN), 5,6-dimethylindan 4 (R = H), and 2,2,5,6-tetramethylindan 4 (R = Me).Some oxidations induced by CAN have also been carried out.It has been found that, with the exception of when Z = tert-butyl, the deprotonation rate of 1.+ is always faster from the CH2Z group than from the CH3 group, independently of the electron-donating or electron-withdrawing nature of Z.The electron-donating groups (OH, OMe, Me), however, exert a larger effect than the electron-withdrawing ones (COOMe, CN).The negligible deprotonation rate from CH2-t-Bu has been ascribed to stereoelectronic effects (the bulky tert-butyl group does not allow the C-H bonds to be collinear with the ?-system), the suggestion being nicely confirmed by the observation that the deprotonation rate from the position 1(3), relative to that from the 5(6)-methyl group, is almost identical in the radical cations of 4 (R = H and Me).The effect of the other α-substituents is mainly of electronic nature and has been rationalized on the basis of a variable transition-state structure for the deprotonation process.It is suggested that with +R groups most of the charge, in the transition state, has been transferred to the Cα-H bond where it can be stabilized by the α-substituent.With electron-withdrawing groups less charge transfer has taken place and the rate-enhancing effects of these groups is ascribed to their capability to significantly decrease the strength of the Cα-H bond.