139527-55-2

Basic information

• Product Name: Pyrrolidine, 3,3,4,4-tetrafluoro-1-(4-methylbenzoyl)-
• CAS NO: 139527-55-2
• Molecular Formula: C12H11F4NO
• Molecular Weight: 261.219
• Mol File: 139527-55-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Pyrrolidine, 3,3,4,4-tetrafluoro-1-(4-methylbenzoyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrrolidine, 3,3,4,4-tetrafluoro-1-(4-methylbenzoyl)-(139527-55-2)
• EPA Substance Registry System: Pyrrolidine, 3,3,4,4-tetrafluoro-1-(4-methylbenzoyl)-(139527-55-2)

Safety Data

• Hazardous Substances Data: 139527-55-2(Hazardous Substances Data)

Upstream product

• 1841-00-5 3,3,4,4-tetrafluoropyrrolidine 
• 874-60-2 4-methyl-benzoyl chloride 

Relevant articles and documents

Base-catalyzed hydrolysis and18O=C exchange kinetics for toluamides containing amine portions of reduced basicity. N-toluoyl-3,3,4,4-tetrafluoropyrrolidine and N-toluoylpyrrole

Base-catalyzed hydrolysis and 18O=C exchange kinetics for N-toluoyltetrafluoropyrrolidine (IV) and N-toluoylpyrrole (V) have been determined as a function of [OH-] at 73 and 25°C respectively, M = 1.0 (KCl). Both amides exhibit KLhyd vs [OH-] profiles that contain First-order and second-order domains in [OH-]. For IV at low [OH-] where both the hydrolysis and exchange kinetics are first order in [OH-], kex/khyd = 9.0, and this value is progressively reduced as [OH-] increases. The solvent kinetic isotope effect for hydrolysis of IV at low [OH-] is slightly inverse (Khyd)H/D = 0.72, and at high [OH-] becomes 1.54, suggestive of a change in mechanism from one involving spontaneous expulsion of amide anion at low [OH-] to one involving a proton in flight concurrent with amide anion expulsion at high [OH-]. For V, the khyd profile from pH 8.5 to 13.7 is approximately linear but shows a small inflection point at pH 10.8. At the same time, the kex vs [OH-] profile for V at low [OH-] is first order in [OH-] (kexkhyd = 0.24) but plateaus above pH 10.8 so that the kex and khyd profiles diverge. The hydrolytic and exchange processes for these amides are analyzed as involving a mechanism wherein the low [OH-] domain involves reversible attack of OH- on the amide to form To- followed by spontaneous C-N cleavage to expel the amide anion either without general acid assistance by solvent or with a small component of it. The difference in the kex/khyd ratios for the two amides is explicable since the pyrrolide anion is a better leaving group than the tetrafluoropyrrolidide anion. At higher [OH-], second-order terms in [OH-] come into play wherein OH- deprotonates To- concurrently with expulsion of the amide anion. This process effectively halts the reversal and 18O=C exchange at high [OH-], since each time To- is produced it immediately undergoes OH- promoted breakdown to products. A unified picture of base promoted hydrolysis of toluamides containing amine portions of basicity varying over ～15 pKa units is presented.