1245725-32-9

Basic information

• Product Name: 2,3,4,5,6-pentafluoro-N,N-dimethylaniline N-oxide trifluoroacetic acid salt
• CAS NO: 1245725-32-9
• Molecular Weight: 341.158
• Mol File: 1245725-32-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2,3,4,5,6-pentafluoro-N,N-dimethylaniline N-oxide trifluoroacetic acid salt(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,5,6-pentafluoro-N,N-dimethylaniline N-oxide trifluoroacetic acid salt(1245725-32-9)
• EPA Substance Registry System: 2,3,4,5,6-pentafluoro-N,N-dimethylaniline N-oxide trifluoroacetic acid salt(1245725-32-9)

Safety Data

• Hazardous Substances Data: 1245725-32-9(Hazardous Substances Data)

Upstream product

• 359-48-8 trifluoroacetyl peroxide 
• 1801-14-5 1-(N,N-dimethylamine)pentafluorobenzene 

Downstream Products

• 1201-02-1 2,3,4,5,6-pentafluoro-N-methylaniline 
• 1801-14-5 1-(N,N-dimethylamine)pentafluorobenzene 

Relevant articles and documents

Anilinic N-oxides support cytochrome P450-mediated N-dealkylation through hydrogen-atom transfer

The mechanism of N-dealkylation mediated by cytochrome P450 (P450) has long been studied and argued as either a single electron transfer (SET) or a hydrogen atom transfer (HAT) from the amine to the oxidant of the P450, the reputed iron-oxene. In our study, tertiary anilinic N-oxides were used as oxygen surrogates to directly generate a P450-mediated oxidant that is capable of N-dealkylating the dimethylaniline derived from oxygen donation. These surrogates were employed to probe the generated reactive oxygen species and the subsequent mechanism of N-dealkylation to distinguish between the HAT and SET mechanisms. In addition to the expected N-demethylation of the product aniline, 2,3,4,5,6-pentafluoro-N,N-dimethylaniline N-oxide (PFDMAO) was found to be capable of N-dealkylating both N,N-dimethylaniline (DMA) and N-cyclopropyl-N-methylaniline (CPMA). Rate comparisons of the N-demethylation of DMA supported by PFDMAO show a 27-fold faster rate than when supported by N,N-dimethylaniline N-oxide (DMAO). Whereas intermolecular kinetic isotope effects were masked, intramolecular measurements showed values reflective of those seen previously in DMAO- and the native NADPH/O2-supported systems (2.33 and 2.8 for the N-demethylation of PFDMA and DMA from the PFDMAO system, respectively). PFDMAO-supported N-dealkylation of CPMA led to the ring-intact product N-cyclopropylaniline (CPA), similar to that seen with the native system. The formation of CPA argues against a SET mechanism in favor of a P450-like HAT mechanism. We suggest that the similarity of KIEs, in addition to the formation of the ring-intact CPA, argues for a similar mechanism of Compound I (Cpd I) formation followed by HAT for N-dealkylation by the native and N-oxide-supported systems and demonstrate the ability of the N-oxide-generated oxidant to act as an accurate mimic of the native P450 oxidant.