73434-13-6

Basic information

• Product Name: Dibenzyl-α,α-d₂-dimethylammonium bromide
• Synonyms: Dibenzyl-α,α-d₂-dimethylammonium bromide
• CAS NO: 73434-13-6
• Molecular Weight: 308.23
• Mol File: 73434-13-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Dibenzyl-α,α-d₂-dimethylammonium bromide(CAS DataBase Reference)
• NIST Chemistry Reference: Dibenzyl-α,α-d₂-dimethylammonium bromide(73434-13-6)
• EPA Substance Registry System: Dibenzyl-α,α-d₂-dimethylammonium bromide(73434-13-6)

Safety Data

• Hazardous Substances Data: 73434-13-6(Hazardous Substances Data)

Upstream product

• 103-83-3 N,N'-dimethylbenzylamine 
• 51271-29-5 [1',1'-2H₂]benzyl bromide 

Downstream Products

• 103-83-3 N,N'-dimethylbenzylamine 
• 538-68-1 pentylbenzene 
• 3535-98-6 α-D-N,N-dimethylbenzylamine 
• 38161-07-8 Benzyldimethylamine-α,α-d₂ 
• 68639-74-7 Pentylbenzene-α,α-d₂ 

Relevant articles and documents

Azetidines. 5. Reaction of 1,1,3,3-Tetramethyl- and 1-Benzyl-1,3,3-trimethylazetidinium Ions with Butyllithium and Phenyllithium. Deuterium Labeling as a Mechanistic Probe

The reactions of 1,1,3,3-tetramethylazetidinium iodide (1) and 1-benzyl-1,3,3-trimethylazetidinium bromide (7) with butyllithium and with phenyllithium were studied in ether.The products from the reaction of 1 with butyllithium were 1,3,3-trimethylpyrrolidine (2), 3,3-dimethyl-4-(methylamino)-1-butene (3), 1-(dimethylamino)-2,2-dimethylheptane (4), neopentylpyrrolidine (5), and 1-(dimethylamino)-2,2-dimethylcyclopropane (6).With phenyllithium, 1 gave 2 and 1-(dimethylamino)-2,2-dimethyl-3-phenylpropane (11).With butyllithium, 7 gave 2-phenyl-1,4,4-trimethylpyrrolidine (8), 1-benzyl-3,3-dimethylpyrrolidine (9), and 1-neopentyl-2-phenylpyrrolidine (10).The reaction of phenyllithium with 7 gave only 8 and 9.Mechanistic information was obtained by labeling 1 with deuterium in three different ways: N-methyl-d3, 2,2-d2, and N-methyl-d3-2,2-d2.A primary kinetic isotope effect of 9.4 was found for the formation of 2 from 1-N-methyl-d3.When 2 was formed from 1-2,2-d2, a secondary kinetic isotope effect of 1.17 was measured.The formation of 4 from 1-2,2-d2 was accompanied by a primary kinetic isotope effect of 4.7, suggesting a carbene intermediate.Ylide carbanions involving decomposition to a carbene carbanion in the formation of 3 and an azomethine ylide in the formation of 5 and 9 are probable intermediates.It is postulated that the azomethine ylides react with ethylene formed from the reaction of butyllithium with the solvent ether by means of a concerted (4 + 2) cycloaddition reaction.A primary kinetic isotope effect of 20 was found for the formation of pentylbenzene from dibenzyldimethylammonium bromide and butyllithium.