110079-37-3

Basic information

• Product Name: [1-(3-Bromo-phenyl)-meth-(E)-ylidene]-ethyl-amine
• Synonyms: [1-(3-Bromo-phenyl)-meth-(E)-ylidene]-ethyl-amine
• CAS NO: 110079-37-3
• Molecular Weight: 212.089
• Mol File: 110079-37-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: [1-(3-Bromo-phenyl)-meth-(E)-ylidene]-ethyl-amine(CAS DataBase Reference)
• NIST Chemistry Reference: [1-(3-Bromo-phenyl)-meth-(E)-ylidene]-ethyl-amine(110079-37-3)
• EPA Substance Registry System: [1-(3-Bromo-phenyl)-meth-(E)-ylidene]-ethyl-amine(110079-37-3)

Safety Data

• Hazardous Substances Data: 110079-37-3(Hazardous Substances Data)

Upstream product

• 110079-28-2 C₉H₁₁BrClN 
• 3132-99-8 m-bromobenzoic aldehyde 
• 75-04-7 ethylamine 

Downstream Products

• 90389-91-6 N-(3-bromobenzyl)ethanamine 

Relevant articles and documents

Reactions of N-(arylsulfonoxy)-N-alkylbenzylamines with MeONa-MeOH. Steric effect on the structure of the imine-forming transition state

Elimination reactions of N-(arylsulfonoxy)-N-alkylbenzylamines 1-5 with MeONa-MeOH have been studied kinetically. The elimination reactions are regiospecific, producing only corresponding benzylidenalkylamines. The rate equation for the reactions is kobs = k0 + k2[MeONa], indicating that the reactions proceed by competing solvolytic- and base-promoted pathways. The relative rates of elimination for the k2 and k0 pathways are 1, 0.67, 0.53, 0.35, and 0.27 for R = Me, Et, i-Pr, s-Bu, and t-Bu and 1, 4.1, 5.1, and 8.7 for R = Et, i-Pr, s-Bu, and t-Bu, respectively. For MeONa-promoted elimination from 1-5, Hammett ρ and kH/kD decrease but ρ1g and |β1g| increase with a bulkier alkyl substituent. However, the values for the solvolytic eliminations are nearly the same for all substrates and are similar to those for the base-promoted pathway, except for the ρ values, which have opposite signs. From these results, the changes in transition-state structure wrought by variation of N-alkyl substituents are assessed.

Reactions of N-Chlorobenzylalkylamines with Sodium Methoxide in Methanol. Steric Effects in Elimination Reactions

Reactions of N-chlorobenzylalkylamines in which the alkyl group is Me, Et, i-Pr, t-Bu, and sec-Bu with MeONa-MeOH have been investigated kinetically.The eliminations are quantitative and regiospecific, producing only benzylidenealkylamines.The reactions are first order in base and first order in substrate, and an E2 mechanism is evident.The relative rates of elimination at 25 deg C are 1/0.5/0.3/0.2/0.01 for Me/Et/i-Pr/sec-Bu/t-Bu alkyl substituents, respectively.The results are attributed to repulsive interaction between the alkyl group and the base in the transition state.Hammett ρ and kH/kD values decreased, but the ΔH(excit.) and ΔS(excit.) values increased with bulkier alkyl substituents.Changes in the transition-state parameters with the substrate steric effect are interpreted with variation in structure of the imine-forming transition states.